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.
Tripadvisor
Talbot County
Post
Inbox
Search

Talbot County Holiday Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
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
    Location
    Any Distance
    from
    Price
    per night
    AU$579 Average
    |||
    |||
    AU$0AU$1,000+
    Suitability
    More filters
    Travellers to Talbot County are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    All 72 Rentals in Talbot County
    Sort by:
    Default
    Waterfront Vacation Home with Private Beach1 / 55
    (5)Average
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    RESTORED WATERFRONT COTTAGE1 / 24
    (10)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Comfortable, Spacious & Fun! 6+ Acres Pool & Shore. 4 Master Suites Waterview1 / 36
    (3)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Large Historic Thomas Harrison House on Harbor in St. Michaels Town1 / 30
    (14)Very good
    7 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Waterfront
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 November 2019
    For our annual fall getaway, my friends and I selected St. Michaels and we could not have been happier with our choice. The town is very charming and walkable with a number of...
    Reviewed 5 August 2019
    This beautiful home is right in the middle of the historic St. Michaels harbor. The water and the benches on Muskrat Park are basically right in your front yard. The place is...
    See all reviews
    About this property
    The historic Thomas Harrison House is located on the harbor in the center of the town of St. Michaels. This Eastern Shore/Chesapeake Bay vacation rental has magnificent water VIEWS and can accomodate up to 12 people. The house is a short walk from all the museums, parks, restaurants, churches, and...
    View all property information
    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 9
    Carpenter St. Cottage in the Heart of St. Michaels - Walk To Everything!1 / 23
    (11)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 August 2019
    The CSH came highly recommended and it did not disappoint. The home was very nicely appointed. The house is much larger than it appears from the front. Large screen porch and...
    Reviewed 29 May 2019
    This is a great location in St. Michaels - a minute walk to the historic district and a minute to the harbor and lighthouse. The setting is beautiful with a wonderful...
    See all reviews
    About this property
    The recently renovated Carpenter St. Cottage is centrally located in village of St. Michaels. The Cottage is just steps to the harbor and to museums, shops, restaurants, parks etc. The house is a 2 bedroom 2 full bathroom house with plenty of living space and a large screened porch facing a large...
    View all property information
    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Location Location! St Michaels-- In Town Cottage!1 / 27
    (24)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Air Conditioning
    • Patio
    • Grill
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 January 2018
    My family and I spent the week after Christmas in St. Michaels in this amazing historic cottage in the heart of town. We nestled in next to the fire most nights, cooked some...
    Reviewed 10 October 2017
    Everything is exactly as pictured! I love the hardwood floors and enjoyed sitting outside on the patio! As noted in the name, this cottage is centrally located to the shops...
    See all reviews
    About this property
    The recently restored historic Washington Melson House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, town pool, parks, restaurants, library, churches and shops in St. Michaels. The house was built around 1840 by Washington Melson, a sailor,...
    View all property information
    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Premier Cottage in St. Michaels- In Town Location!1 / 24
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Grill
    • Air Conditioning
    • Washer
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 May 2019
    Like other prior reviews, the location of the Thomas Blades House is perfect. One short block to the waterfront Muskrat Park and one block to the heart of Talbot St and and it's...
    Reviewed 28 July 2017
    Very clean, very cute rental! The location could not be better. One block from Talbot St, where all the shops and restaurants are, and one block form the marina. only complaint...
    See all reviews
    About this property
    The historic and recently restored Thomas Blades House is a 2 bedroom, 1.5 bathroom vacation cottage that is a short walk from the harbor, all museums, parks, restaurants, town pool, library, churches and shops in St. Michaels. The house was built around 1850 by Thomas Blades, a young sailor....
    View all property information
    Location Information
    St. Michaels, Talbot County NA
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Waterfront Room Rentals 1 with Private Beach1 / 34
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Internet Access
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 September 2018
    Dimitri was very kind and helpful. We throughly enjoyed our stay. The view of the Choptank was beautiful.
    See all reviews
    About this property
    Great setting for a getaway relaxing weekend in a waterfront setting with a private beach. A variety of places to visit in the area, and fun outdoor activities. Two night minimum stay on weekends please. Swimming, fishing and lots of sunbathing. Amazing sunsets! This room is the master bedroom...
    View all property information
    Location Information
    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Waterview Cottage In St. Michaels!1 / 25
    (5)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Parking
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 October 2019
    My wife and I just got back from a wonderful few days at a beautifully restored historic cottage in St MichaelsCozy, comfortable with incredible water view Watched the...
    Reviewed 29 March 2019
    We had a wonderful stay at the John Bruff House. The house was very comfortable and decorated beautifully. The property has magnificent views of the harbor and park, and is a...
    See all reviews
    About this property
    The fully restored historic John Bruff House, located on the Town park, has magnificent St. Michaels harbor and Miles River water views. The house is 2 bedroom, 3 bathroom cottage with plenty of living space and a rear screened porch. It is a short walk from all museums, parks, restaurants,...
    View all property information
    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
    Waterfront Room Rentals 2 with Private Beach1 / 40
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great setting for a getaway relaxing weekend in a waterfront setting with a private beach. A variety of places to visit in the area, and fun outdoor activities. Two night minimum stay on weekends please. Swimming, fishing and lots of sunbathing. Amazing sunsets! This room is the master bedroom...
    View all property information
    Location Information
    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Save time - get the best Talbot County rentals sent straight to your email!
    Get the List
    Cottage 2 at Grandview Pleasure Point1 / 9
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Porch
    • Patio
    • Grill
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, valences, sofas, wing and lounge chairs and collectibles. All the cottages are fully furnished including solaria porch, gas fireplaces,...
    View all property information
    Location Information
    Bozman, Talbot County 21612
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Ingleton! Relax by the pool. Fish or crab or picnic at the end of the pier. Do all three. Go biking. Go hiking. Go boating. Visit historic St. Michaels, Easton and Oxford. Watch the sunset from the Adirondack chairs at the water's edge. Eat. Shop. Play golf. Play yard games. Play board...
    View all property information
    Location Information
    Royal Oak, Talbot County 21601
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Internet Access
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great setting for a getaway relaxing weekend in a waterfront setting with a private beach. A variety of places to visit in the area, and fun outdoor activities. Two night minimum stay on weekends please. Swimming, fishing and lots of sunbathing. Amazing sunsets! This room is the master bedroom...
    View all property information
    Location Information
    Trappe, Talbot County 21673
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The ambiance of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, new sleep sofas, wing chairs and sleeper lounge chairs, as well as antiques, reproductions and other eclectic furnishings All the...
    View all property information
    Location Information
    Bozman, Talbot County 21612
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Main House at Grandview at Pleasure Point1 / 34
    (13)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Unheated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 November 2018
    This is our 4th year coming to the St. Michaels area for our anniversary. This was our first time staying at the grand view. We were in cottage 1B. PerfectLocation, quiet...
    Reviewed 21 September 2018
    What a terrific week we had . Young and old enjoyed our stay. Perfect weather and plenty of crabs made our visit special. Grandview is the perfect family vacation spot.
    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 - 5 Bedrooms, 3 Bathrooms, Sleeps 13
    Sandy Pines:  Enjoy Harris Creek w/Pool and Boats1 / 22
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Internet Access
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2018
    Took the whole family for a big birthday weekend and the house was perfect. Owner Brad is very responsive and booking was a breeze. The house was spacious, clean, and even has a...
    Reviewed 27 January 2017
    We had a group of women here to celebrate a birthday. We wanted to hang out, relax, eat, drink, and sleep and were pleased with our choice to stay at Sandy Pines. The view is...
    See all reviews
    About this property
    Sandy Pines, with its own waterfront, dock, and swimming pool, offers a peaceful retreat within the quiet natural beauty of the Chesapeake Bay region. The very private home, sited on broad Harris Creek, enjoys stunning sunset views across the Chesapeake tributary, and is fully-equipped and...
    View all property information
    Location Information
    St. Michaels, Talbot County 21612
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Phenomenal Vacation Rental by Water in St Michaels - Walk to Town! 4 ADULTS MAX1 / 18
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 July 2017
    Very beautifully decorated place very clean and well taken care of on a very quiet street just a block from the water and about a fifteen minute walk to the hart of st michaels...
    Reviewed 4 July 2017
    The location was perfect - about a 10 minute walk to the central part of St. Michael's. If you prefer to drive, it will only take you about 2 minutes. The owner was helpful...
    See all reviews
    About this property
    Near the water, near the town. Steps to shopping, winery, brewery and more. Enjoy the former renowned painters studio remade into a loft for sleeping, chilling out. You're close to everything at Long Lane Lodge - no need to drive! Enjoy grilling out or building a firepit. St. Michaels has it all....
    View all property information
    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The 'Land of Pleasant Living' awaits your arrival at Blue Bird Cottage, a 2-bedroom, 2-bathroom Neavitt vacation rental house! Numerous amenities and spectacular peninsula location within walking distance to the water and marina provide up to 4 guests with a serene Maryland getaway. Venture to St....
    View all property information
    Location Information
    Neavitt, Talbot County 21652
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Washer
    • Waterfront
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cranford on the Miles is a waterfront home located on 3+ acres, in St. Michaels. Fully renovated, with Wi-Fi, there is a Master Bedroom with king bed, sitting room, and private balcony; Second Bedroom with a double bed; Third Bedroom with both a double and twin bed; and a Den with a trundle bed...
    View all property information
    Location Information
    St. Michaels, Talbot County 21653
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The ambience of each cottage is one of relaxed comfort. Fashionable cottage decor is enhanced with coordinating spreads & dust ruffles, moldings, 2” wood blinds, new sleep sofas, wing chairs and sleeper lounge chairs, as well as antiques, reproductions and other eclectic furnishings All the...
    View all property information
    Location Information
    Bozman, Talbot County 21612
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    List your property for free!
    List your holiday rental where Tripadvisor travellers can find it.
    Add a Listing
    Pot Pie House1 / 12
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2016
    Absolutely lovely stay! The home is spotless and cozy, set in a secluded neighborhood just a short drive away from St. Michaels, so we had our choice of easily getting into town...
    See all reviews
    About this property
    Pot Pie House - Newly Renovated Historic Cottage Located Close to St. Michaels MD Welcome to Pot Pie House! Immerse yourself in Eastern Shore culture in this newly renovated historic cottage located in the quaint waterfront village of Wittman, just minutes from St. Michaels. According to locals,...
    View all property information
    Location Information
    St. Michaels, Talbot County 21676
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Time to book your 2020 Sunset vacation!1 / 21
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Tilghman, Talbot County 21671
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Cable/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
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Waterfront
    • Washer
    • Private Garden
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unique apartment sleeps 5 and is part of the elegant house sitting on 17 private acres in historic Wye Mills with access to a lake. This place is perfect for kayaking, fishing and an overall countryside experience abundant with wildlife. Wye Mills is home to the historic Old Wye Grist Mill...
    View all property information
    Location Information
    Wye Mills, Talbot County 21679
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Housekeeping Included
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Easton, Talbot County 21601
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Housekeeping Included
    • Patio
    • Parking
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Easton, Talbot County 21601
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    St. Michael's Premier in Town Summer Cottage!1 / 7
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other traveller has booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping Included
    • Grill
    • DVD Player
    • Internet Access
    • Washer
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 July 2019
    My three sisters and I stayed here for two nights in June and loved this cottage. Even before arriving, I had a good feeling because Carol, the owner, is very responsive and...
    See all reviews
    About this property
    Harbor Hideaway's in town location is a rare find! HH's in town location is just steps away from everything that St. Michael's has to offer, including the public access to the water! A charming story and a half cottage that has been completely renovated with amenities that will help ensure a great...
    View all property information
    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    St. Michaels award-winning waterfront BayCottage, pool, docks, sundeck, grounds1 / 38
    (1)Average
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
    other travellers have booked this property
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2017
    We rented Bay Cottage for two weeks and were looking forward to the six bedroomhouse and large waterfront property with pool and dock on the MIles River. We arrived to find a...
    See all reviews
    About this property
    A St. Michaels 3.5-acre waterfront vacation rental property with 500' shoreline, private pier, deep-water boat slips, dinghy dock, waterside pool, fire pit, and sundeck. We offer the warmest hospitality and the finest comfort. Walk to St. Michaels, MD attractions - shops, restaurants, brewery,...
    View all property information
    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Parking
    • Internet Access
    • Washer
    • Patio
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Oxford, Talbot County 21654
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    AWARD WINNING WATERFRONT VACATION HOME WITH POOL AND DOCK DISCOUNTS FOR AUGUST1 / 30
    (2)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • DVD Player
    • Washer
    • Patio
    • Internet Access
    • Balcony
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    Newly available rental:  Relaxing Waterfront Cottage Near St Michaels, Maryland1 / 34
    (59)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Parking
    • Washer
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Wittman, Talbot County 21676
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Large waterfront estate with breathtaking sunset views1 / 29
    (31)Very good
    8 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Internet Access
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Wittman, Talbot County 21676
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 12
    Fully remodel 2 bedroom country cottage.1 / 14
    (26)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Washer
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Tilghman, Talbot County 21671
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Escape To This Oxford, Md Waterfront Home - Kayaking, Canoeing & Relaxing1 / 24
    (36)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Washer
    • DVD Player
    • Balcony
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Oxford, Talbot County 21654
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Comfy home on beautiful Leadenham Creek. Book now for summer!1 / 25
    (15)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Washer
    • Parking
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Bozman, Talbot County 21612
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Romantic Retreat  on Chesapeake Bay with Gorgeous Sunsets1 / 16
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Internet Access
    • DVD Player
    • Patio
    • Parking
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Tilghman, Talbot County 21671
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    St. Michael's Waterfront Vacation Cottage1 / 27
    (40)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Parking
    • Patio
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Royal Oak, Talbot County 21662
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    TRUE IN-TOWN SAINT MICHAELS 5.5 ACRE WATERFRONT w/POOL!!!1 / 40
    (21)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 8
    Charming Waterfront Cottage Outside St. Michaels Close to the Oaks1 / 30
    (25)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Washer
    • Parking
    • Air Conditioning
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Royal Oak, Talbot County 21662
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Elegant, Waterfront Cottage on Six Acres in Historic Area1 / 24
    (22)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Washer
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Patio
    • Air Conditioning
    • Parking
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Micheals / Easton1 / 49
    (22)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Washer
    • Parking
    • Patio
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Easton, Talbot County 21601
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Spectacular Sunsets , Fantastic Home on Chesapeake Bay1 / 32
    (22)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Patio
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Tilghman, Talbot County 21671
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Delightful Close to town1 / 18
    (15)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Washer
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Waterfront Serenity w/Pool, Kayaks, Dock mins. to Best Eastern Shore Attractions1 / 43
    (25)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Parking
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Easton, Talbot County 21601
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    St. Michael's Waterfront Vacation Home1 / 20
    (22)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Parking
    • Patio
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Royal Oak, Talbot County 21601
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Private Lakefront Home on 17 acres in historic town, w/ a Canoe & Organic Garden1 / 24
    (26)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Washer
    • Parking
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Wye Mills, Talbot County 21679
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Waterfront Home with Magnificent Views1 / 25
    (23)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Patio
    • Air Conditioning
    • Balcony
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Parking
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Wittman, Talbot County 21676
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    FALL ESCAPE - Private Residence on Harris Creek1 / 34
    (26)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Air Conditioning
    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Wittman, Talbot County 21676
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 6
    Cottage downtown on a quiet street1 / 30
    (36)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Classic Eastern Shore Waterfront Manor House1 / 23
    (9)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Patio
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    St. Michaels, Talbot County 21663
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    1
    List your property
    Owner log in