We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Grasonville Holiday Homes

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    $532 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Grasonville area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 44 Rentals in Grasonville
    Sort by:
    Default
    The following rentals are within 25 kilometres of Grasonville.
    Charming and Spacious Annapolis Victorian1 / 24
    (3)Excellent
    Annapolis
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Beautiful Murray Hill Home (Annapolis)1 / 30
    (3)Very good
    Annapolis
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Beautiful Eastport Home, Walk to Naval Academy1 / 15
    (2)Excellent
    Annapolis
    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Annapolis
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • DVD Player
    • Patio
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We bought and renovated this rowhouse in 2007 for a second home for friends and family to stay when they visited and it eventually evolved into one of the most popular rental properties in all of Historic Annapolis. A former " Home of the Week" in the Capital Gazette it is also one of the most...
    View all property information
    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    Stevensville
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Patio
    • Balcony
    • Washer
    • Central Heating
    • Terrace
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of your everyday stress. Leave...
    View all property information
    Location Information
    Stevensville, Kent Island 21666
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Annapolis
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Patio
    • Washer
    • Grill
    • Satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Your family will thank you for choosing this Severn River Waterfront Retreat for Vacation! From the moment you enter this 5 bedroom home you will appreciate the spectacular views of the Severn River. Four of the five bedrooms view the Severn River, so your family will love waking up to views of...
    View all property information
    Location Information
    Annapolis, Maryland 21032
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
    Make Enquiry
    Captain's Quarters, a waterfront  couples retreat1 / 12
    (1)Excellent
    Rock Hall
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2017
    Lovely, comfortable,clean, friendly with direct access to dock and bay. Lovely views from the many windows. Space is bright and modern while still sortingva large claw foot tube...
    See all reviews
    About this property
    Enjoy the gentle tidal waters of the Chesapeake Bay and its tributaries from your private overlook. The Captain’s Quarters at Spring Cove is a crisp and contemporary second floor living space with great water views. An exterior stairway leads to an ample deck where you can enjoy breakfast and...
    View all property information
    Location Information
    Rock Hall, Maryland 21661
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Stevensville
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of your everyday stress. Leave...
    View all property information
    Location Information
    Stevensville, Kent Island 21666
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Waterfront Cottage at Spring Cove1 / 15
    (2)Very good
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 September 2014
    My sisters and mother stayed three nights in this quaint house with great views of one of the marina's and cove area. The downstairs was perfect my mother, with a screened in...
    Reviewed 19 August 2014
    My family was looking for a relaxing getaway that would be an alternative to another week at the beach. We found the perfect spot at this cottage near Rock Hall. We rented with...
    See all reviews
    About this property
    The Cottage takes advantage of its unique environment with a large deck overlooking the extensive lawn and the tranquil waters of Spring Cove. The deck includes a dining set and barbeque grill.The first level includes a screened porch accessed through a first floor bedroom The Cottage is oriented...
    View all property information
    Location Information
    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Annapolis
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Waterfront
    • Satellite TV
    • DVD Player
    • Grill
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront Property (built in 2000) minutes outside Annapolis, Maryland. Expansive views of the river from this gated custom built home (2176 sq ft excluding basement) with 278' pier on private lot with your own 50' sandy beach. This comfortable home boasts 3-4 bedrooms (and Murphy bed in the...
    View all property information
    Location Information
    Annapolis, Maryland 21146
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Peaceful 3BR Annapolis House on Oyster Creek w/ Amazing Views of the Chesapeake Bay1 / 26
    (1)Average
    Annapolis
    3 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Washer
    • Internet Access
    • Patio
    • Balcony
    • Air Conditioning
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 September 2016
    Location quiet with good views.Disappointed that house was advertised with hot tub which was one of the main reasons this home was selected, and there was no hot tub. Owner...
    See all reviews
    About this property
    Come stay in this beautiful 3-bedroom, 3.5-bathroom single-family home on Oyster Creek – You’ll be able to enjoy fantastic views of the Chesapeake Bay from almost every single room! There’s enough room for 9 guests to comfortably sleep here, so it’s a great size for a family retreat. The...
    View all property information
    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 9
    Make Enquiry
    *BOOK NOW* Beautiful Cottage in historic Annapolis1 / 25
    (15)Excellent
    Annapolis
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Porch
    • Grill
    • Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 December 2016
    We absolutely loved our time in this home! We were in town for the Annapolis Half Marathon. We walked to the starting line from the house, and even walked downtown and the...
    Reviewed 9 November 2016
    This quaint home has loads of charm and plenty of space. Convenient to all the locations that were important to us, we walked to the Navy-Marine Corp Memorial Stadium and only...
    See all reviews
    About this property
    Half a block to walk to the Naval Academy Stadium and minutes away from stunning Annapolis town center. This adorable little cottage has lots of sleeping and great outdoor space. <BR>Sun Porch & Plenty of parking.<BR>A perfect place to relax and enjoy Annapolis, the property is available all year...
    View all property information
    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    * 3 Bedroom Rental House in Historic Rock Hall MD1 / 17
    (3)Excellent
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Satellite TV
    • Patio
    • DVD Player
    • Porch
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Spacious Home provides 3 Bedrooms and 2 bathrooms. Each room sleeps 2 people comfortably, and an old fashion cot is provided to sleep one more. This home is completely equipped with all the comforts of home. The Central location is in the heart of the Marina district, steps from Waterman’s...
    View all property information
    Location Information
    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    Charming Home close to historic district1 / 29
    (2)Excellent
    Annapolis
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Wi-Fi
    • Grill
    • Porch
    • Air Conditioning
    • Washer
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 December 2016
    My two friends and I wanted a place to get away close to our homes in PA and we found it.Annapolis provided everything we were looking for and the house was beautiful and...
    See all reviews
    About this property
    A Charming detached one-family home located in one of the most vibrant neighborhoods of Annapolis. Perfectly located in a quiet residential street, only 0.8 miles from the United States Naval Academy and a short walk from Main street. The home is situated only a few steps away from West street and...
    View all property information
    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Annapolis Waterfront very near USNA1 / 19
    (1)Excellent
    Annapolis
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Grill
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 April 2017
    A clean, peaceful retreat with spectacular views; that is exceptionally stocked!I had no need to buy anything! At one point, I asked the owner if/or where the hand mixer was...
    See all reviews
    About this property
    Waterfront timber frame large cottage in Annapolis, MD. Private, wooded setting with excellent views. Please inquire to the property owner for rates and quote. This house is an energy efficient 9 year old house perched atop a small bluff overlooking picturesque Mill Creek and an...
    View all property information
    Location Information
    Annapolis, Maryland 21409
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    McDaniel
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Halo's Haven is a true piece of Heaven!! Bring your boat and your bathing suit. Twenty picturesque acres on a beautiful point of land off of the Chesapeake Bay near historic St. Michael's, Maryland. This property is beautifully landscaped, has a waterfront pool, pool house with bathroom, boat dock...
    View all property information
    Location Information
    McDaniel, St. Michaels 21647
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Walk to Shops/Eateries Charming Cottage. Dogs Wel.1 / 50
    (1)Excellent
    Annapolis
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Grill
    • DVD Player
    • Housekeeping Included
    • Patio
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This City-inspected vintage cottage in Upper Eastport, located on a cul de sac, is a short walk to the Historic Harbor & just blocks from Spa Creek. History, waterfront, rooftop restaurants, wine bars, sailing, kayaking and more. We have everything here in Annapolis - USNA, sailing, culture,...
    View all property information
    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    ENDLESS SUNSETS - The perfect getaway!1 / 11
    (5)Excellent
    Claiborne
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Washer
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 June 2015
    We were a group of two couples each with a young child. There was more than enough room for the 6 of us. The home is well located in Claiborne, about 5 min from downtown...
    Reviewed 11 October 2014
    Very new, very clean, very spacious, very comfortable. The family thoroughly enjoyed our stay here with plenty of room to spread out, a huge kitchen, meals on the deck and...
    See all reviews
    About this property
    Beautiful like new waterfront home on the Chesapeake Bay, 5 minute drive to Historic St. Michaels. Minutes to many quaint watermen villages. Shared waterside pool, beach, kayaks, small boat, childrens playset. The property was designed to take advantage of the incredible views of the Chesapeake...
    View all property information
    Location Information
    Claiborne, Talbot County 21663
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Waterfront House, Eastern Shore Chesapeake Bay1 / 34
    (21)Excellent
    Centreville
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Internet Access
    • Porch
    • Satellite TV
    • Grill
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We welcome your inquiries and would be glad to answer any questions you have before booking. In response to inquiries and booking requests, we will send you our standard rental agreement for your information and approval. This house is on the estate of John Raskob, builder of the Empire State...
    View all property information
    Location Information
    Centreville, Maryland 21617
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Annapolis
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROTECTED WATERS, GREAT ANCHORAGES... …gorgeous natural scenery, unique towns and villages, and a forgiving bottom make the Chesapeake an excellent choice for sailors, novice and expert alike. Historic Annapolis, the crown jewel of the Mid-Atlantic, is the best sailing destination on the East...
    View all property information
    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    Wittman
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Washer
    • Patio
    • Grill
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shipwright Cottage is a fully-renovated 2 bedroom, 1 1/2 bath house that is a perfect getaway for couples or small families. Upstairs features two sleeping areas - a bedroom with two extra long twin beds that can be combined to make a king and an open, loft-style bedroom with a queen bed and...
    View all property information
    Location Information
    Wittman, Talbot County 21676
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Charming Townhouse - Steps to City Dock and USNA1 / 7
    (1)Terrible
    Annapolis
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • DVD Player
    • Central Heating
    • Internet Access
    • Grill
    • Patio
    • Washer
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shellback house is a three bedroom, one and 1/2 bath historic townhouse in the heart of Downtown Annapolis with a private garden. The house has views of Ego Alley (Annapolis Waterfront) from the front stoop and the master bedroom. BOOK NOW FOR 2015 LEGISLATIVE SESSION AT STIPEND RATES! Please...
    View all property information
    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Annapolis
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • DVD Player
    • Parking
    • Washer
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A perfect home to enjoy time in Annapolis!  Located on King George Street, walking distance to the Academy or downtown, this home is open year round with a 2-night minimum stay. It is an outstanding home for Weddings, Academy Events, Alumni Gatherings or Family Vacations.  This stunningly...
    View all property information
    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
    Make Enquiry
    Easton
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Wi-Fi
    • Waterfront
    • Ocean Views
    • Washer
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4+ acres on Shipshead Creek off of St. Michaels road. Fully furnished (2 king and 4 twin beds), heated pool, deep water dock, tennis court,and pet friendly. Boat, Jet Ski, Paddle Board, Kayak, Canoe, and Bike rentals can be arranged-Inquire if interested The Space Pet Friendly waterfront...
    View all property information
    Location Information
    Easton, Talbot County 21601
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Cape Saint Claire
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    located in a safe residential neighborhood with free parking. We are close to shopping, restaurants and the Chesapeake Bay; just minutes drive to the naval academy and downtown Annapolis. Our space is super clean, super spacious, and super comfortable! We are committed to providing you a great...
    View all property information
    Location Information
    Cape Saint Claire, Maryland 21409
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    Make Enquiry
    Annapolis
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is a 5 bedroom quality built home. This room is an office converted in to an extra bedroom space for guests to enjoy. It is located on the main level just inside the main entrance. It had double french doors which lock for privacy. Its a clean and cozy space and an expensive way to travel....
    View all property information
    Location Information
    Annapolis, Maryland 21409
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Stevensville
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Waterfront
    • Balcony
    • Housekeeping Included
    • Ocean Views
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to our private luxury waterfront property that sits on 17 acres located on the Chester River where it meets the mouth of the Chesapeake Bay on Maryland's Eastern Shore. Get away from the city and enjoy the scenic view while having fun on the water. Love Point Bay Luxury Waterfront is at the...
    View all property information
    Location Information
    Stevensville, Kent Island 21666
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    Amazing Waterfront Annapolis & easy walk downtown1 / 24
    (1)Very good
    Annapolis
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Waterfront
    • Hot Tub
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 October 2015
    Myself and five coworkers rented this house for a meeting. As we are from different areas across the country we usually meet at hotels. I thought we would try something...
    See all reviews
    About this property
    A Peaceful Oasis Overlooking Annapolis Waterfront and easy walking distance to downtown. Check out this great video of the home & property. Cut and paste the following link: AnnapolisWaterfrontRentals..om This incredible home has 100' of floor-to-ceiling windows nestled in the tree canopy for...
    View all property information
    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
    Make Enquiry
    Annapolis
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • DVD Player
    • Secure Parking
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Balcony
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Best location in Eastport ,We restored this lovely victorian house over the past sixteen years. The upstairs is modern and has all the great amenities that a renovated building provides. anderson windows to keep the place warm and toasty. Seperate heating/air conditioning controls.Wooden floors,...
    View all property information
    Location Information
    Annapolis, Maryland 21403
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    RESTORED WATERFRONT COTTAGE1 / 24
    (10)Excellent
    Royal Oak
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You can tell right away, from the warm sage green exterior and the peaceful creekside setting, that this charming vacation cottage promises a fun, relaxing getaway. With a 180 degree expanse of spectacular Oak Creek waterfront, the River House at Royal Oak is the pefect choice for year 'round...
    View all property information
    Location Information
    Royal Oak, Talbot County 21662
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    Annapolis
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My place is good for couples, solo adventurers, and business (URL HIDDEN) school just down the street , Great location for naval academy parents for parents day etc. A gourmet kitchen if you prefer to cook your own meals or cook your fish you have caught on your fishing trip on the bay,we can...
    View all property information
    Location Information
    Annapolis, Maryland 21403
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Annapolis
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Private Garden
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Walk to historic City Dock, waterfront restaurants, U.S. Naval Academy. Open, sunny floor plan ideal for entertaining. Craftsman style 3 BRM + den + office + front porch swing + screened back porch + game room + ample parking. Well-furnished. Sleeps 6-8 comfortably or up to 10 with available...
    View all property information
    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    Annapolis
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Outdoor Dining Area
    • DVD Player
    • Balcony
    • Washer
    • Parking
    • Porch
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    HOUSE<BR>This fully renovated, circa 1890 ,Victorian house is located in the middle of the Eastport peninsula . The house is within walking distance, or a three minute taxi ride, to downtown historic Annapolis and the US Naval Academy, as well as shopping, several marinas, theater, numerous...
    View all property information
    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Make Enquiry
    Annapolis
    5 Bedrooms, 3 Bathrooms, Sleeps 20 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Ocean Views
    • Hot Tub
    • Internet Access
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfort & Style: Enjoy stunning Chesapeake Bay Views, Beach, Pier, Boat Slips, Park, Water Access, Fire Pit, Patio Heater and more! Charming cottage & detached studio/game room (both upgraded in 2013) offer gourmet kitchen with new stainless steel appliances, a second full kitchen in garden...
    View all property information
    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 20
    Make Enquiry
    Annapolis
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is the newly renovated 780 sf studio unit that is on the ground floor of a main house that is similarly titled and on the same property. Striking and dramatic 8700 - 9000 sf contemporary, new loft style renovation of the main house with exposed structure and mechanical systems that serves as...
    View all property information
    Location Information
    Annapolis, Maryland 21401
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Annapolis
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • Terrace
    • DVD Player
    • Central Heating
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is in a very nice, safe neighborhood (two blocks to firehouse and 2 blocks to police station) within walking distance to historic downtown Annapolis. It is also less than a block to the Navy football stadium and easily walkable to grocery store, pharmacy, liquor store and...
    View all property information
    Location Information
    Annapolis, Maryland 21401
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Make Enquiry
    Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)1 / 21
    (3)Excellent
    Chester
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Patio
    • Satellite TV
    • Waterfront
    • Wi-Fi
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 January 2016
    We have stayed in this home several times and will return in July. It is a wonderful house with a private master suite at one end, two bedrooms with a 2nd bath at the other.The...
    Reviewed 29 July 2013
    First I would like to say thanks, to Harry, and Scott. They were the best host, I've encountered. They have a property, they can be proud of. The house was just excellent...
    See all reviews
    About this property
    Waterfront Rancher on 3 acres, centrally located between Washington DC, St. Michaels, Annapolis, and Baltimore. 4 Bed/2 Bath home with central air sleeps 8. This home has been in our family for over 50 years and is a special place. Over the years there have been many updates to the home. The...
    View all property information
    Location Information
    Chester, Kent Island 21619
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Annapolis
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Waterfront
    • Satellite TV
    • Wi-Fi
    • Grill
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Yellow House is a magnificent Waterfront Property, with interior and exterior appointments, that are truly outstanding-76 five Star reviews can be viewed on our sister site-vacation rentals by owner dot com. 230476 With its magazine worthy gardens, and spacious 6 bedrooms, designed and...
    View all property information
    Location Information
    Annapolis, Maryland 21403
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
    Make Enquiry
    Rock Hall
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Washer
    • Grill
    • Parking
    • Porch
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming 3 bed / 1 bath single family home with screened in front porch. Relax on the rocking chairs as you take in the charm of this lovely town on one of the prettiest streets in Rock Hall. Ample parking, large back yard with BBQ, tables and chairs to relax with family and friends after spending...
    View all property information
    Location Information
    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
    Make Enquiry
    Impressive 3BR Stevensville House Overlooking Eastern Shore w/Wifi, Private Swimming Pool & Game Room - Minutes From the Beach, Golfing & More!1 / 26
    (1)Excellent
    Stevensville
    3 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 May 2016
    From the moment you ride up the driveway you already know you are in for a wonderful experience. From the cathedral ceilings to the beautiful decor this home welcomes you. The...
    See all reviews
    About this property
    Have the ultimate Maryland getaway by staying at this remarkable Stevensville vacation rental home, surrounded by approximately 20 breathtaking acres of open space with picturesque Eastern Shore views. Whether you're in the mood for a relaxing escape in the great outdoors or a vacation filled with...
    View all property information
    Location Information
    Stevensville, Kent Island 21666
    Holiday Rental House - 3 Bedrooms, 5 Bathrooms, Sleeps 8
    Make Enquiry
    Grandview at Pleasure Point1 / 34
    (10)Excellent
    Bozman
    8 Bedrooms, 6 Bathrooms, Sleeps 27 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Satellite TV
    • Patio
    • Internet Access
    • Washer
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 November 2016
    We thoroughly enjoyed our stay in one of the little cottages on the property. We arrived late Friday night and the property sign was not lit up, so it took a while to find it...
    Reviewed 10 June 2015
    Perfectly situated on the water. The views are amazing, as is the pool. There is a huge lawn which is perfect for children of all ages. A short drive to St. Michael's, which is...
    See all reviews
    About this property
    Main House: Beautiful NEW kitchen... Featuring two interior eating/serving areas, custom french windows that open to a sitting area on the porch, 4 bedrooms & Enclosed Sleeping Porch 2 ½ baths, fireplace, 3 TV’s, DVD, cable, wireless internet, large living room, dinning room, screened porch,...
    View all property information
    Location Information
    Bozman, Talbot County 21612
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 27
    Make Enquiry
    Annapolis
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Internet Access
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Known as the “Athens of America,” Annapolis is a city abundant with history and culture. This former capital of the United States has a little something for every interest and taste, whether you're a history buff, a sports enthusiast, or someone simply looking for a peaceful retreat!   Have the...
    View all property information
    Location Information
    Annapolis, Maryland 21403
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Luxury vacation condominum with private beach1 / 35
    (13)Excellent
    Chester
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Hot Tub
    • Waterfront
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Secure Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 January 2016
    My family used this home for 10 days over Christmas and New Year. It was just perfect. Plenty of room for our Christmas tree, decorations and packages. Spotlessly clean bedrooms...
    See all reviews
    About this property
    Swan Cove Condominiums at Kent Narrows(#49064) with private beach and views of the Chesapeake bay! - Brand new luxury condominium with 3000 sq ft, 4 bedrooms, 3 ½ bathrooms, one large family room with open kitchen, one large sunny living room and dinning area. There are 2 king size bed, 2 queen...
    View all property information
    Location Information
    Chester, Kent Island 21619
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    Stevensville
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Patio
    • Waterfront
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you’re searching for the perfect place for a family retreat in Stevensville, look no further than this 5-bedroom, 2-bathroom vacation rental house which sleeps 12 in scenic Kent Island. Situated on the shores of Chesapeake Bay, this spacious home boasts 2,600 square feet, plenty of outdoor space...
    View all property information
    Location Information
    Stevensville, Kent Island 21666
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
    Make Enquiry
    List your property
    Owner log in