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Holiday Homes and Apartments Preston, MD and nearby

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    All 21 Rentals in the Preston Area
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    The following rentals are within 30 kilometres of Preston, Maryland.

    From
    $115
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    1 / 32
    5 of 5 stars (2) Excellent
    Trappe
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
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    $908
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    1 / 38
    4.5 of 5 stars (3) Very good
    Church Creek
    3 Bedrooms / 2 Bathrooms / Sleeps 9
    Overview Reviews (3) Make Enquiry
    From
    $640
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    1 / 18
    5 of 5 stars (6) Excellent
    Cambridge
    6 Bedrooms / 3 Bathrooms / Sleeps 18
    Overview Reviews (6) Make Enquiry
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    $1,407
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    1 / 22
    5 of 5 stars (5) Excellent
    Cambridge
    7 Bedrooms / 6 Bathrooms / Sleeps 28
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Private Fishing...
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    Experience the lavish surroundings of Captain's Quarters. Whether your pleasure is sailing, fishing, water sports, relaxing by the pool and jacuzzi or nestling up on the veranda with a good book, Captain's Quarter's provides luxury around every corner. This unrivaled waterfront estate accommodates... View all property information
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    Location Information
    Cambridge, Maryland 21613
    5 of 5 stars Reviewed 22 May 2014
    I had my wedding at this property. The landlord, Frank, was very polite and easy going. He allowed for our dogs to stay for a low fee and was very good at returning calls. The...
    5 of 5 stars Reviewed 4 August 2012
    I would not change a single thing. Our family enjoyed the six day stay at this awesome place. The amenities were great, the location was central to other sights, and the...
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    $576
    / Night
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    1 / 13
    5 of 5 stars (5) Excellent
    St. Michaels
    3 Bedrooms / 3 Bathrooms / Sleeps 10
    travellers have booked this property
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Beautiful in town location! Just steps to shops, restaurants, winery, brewery, community pool, museums, boat ramp, and waterfront. This home has been renovated with amenities that will ensure a great time in St. Michaels. Home has three bedrooms; main floor master with a king and full bath,... View all property information
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    Location Information
    St. Michaels, Talbot County 21663
    5 of 5 stars Reviewed 10 September 2014
    The home was absolutely beautiful. Right around the corner from the town. Perfect location! We had been to St. Michaels 3 times before this trip and now we finally found our...
    5 of 5 stars Reviewed 20 August 2014
    Very comfortable, well furnished and equipped house with both modern and historical features. We took advantage of the great location to walk to tourist sites, restaurants and...
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    $1,535
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    1 / 39
    5 of 5 stars (2) Excellent
    Cambridge
    5 Bedrooms / 4 Bathrooms / Sleeps 18
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Swan Cove awaits your family vacation or group! It's also an ideal place for a most memorable wedding. This incredible, newly redesigned waterfront home with a private dock offers spectacular views with a large swimming pool, 4 kayaks, outdoor firepit (firewood is furnished), playground and a large... View all property information
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    Location Information
    Cambridge, Maryland 21613
    From
    $574
    / Night
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    1 / 30
    4.5 of 5 stars (9) Very good
    Cambridge
    6 Bedrooms / 5 Bathrooms / Sleeps 16
    Overview Reviews (9) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Private Fishing...
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Fabulous, recently-built premier vacation home on 500 feet of Chesapeake waterfront. A gorgeous home; beach, dock, private pool, boats, bikes, porches & mile-wide view With 6 acres of property, wide water & sandy beaches, this private luxury vacation rental is minutes from Cambridge,... View all property information
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    Location Information
    Cambridge, Maryland 21677
    4 of 5 stars Reviewed 2 April 2014
    We had a group of 9 women stay here for a crafting weekend. The house was perfect for us. We brought a few folding tables and were able to all be in the large open rooms together...
    3 of 5 stars Reviewed 29 July 2013
    Our family spent a week at Saddle Beach House on the Eastern Shore over 4th of July. Unfortunately it was not the vacation we were hoping for. We chose this property because of...
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    $249
    / Night
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    1 / 13
    5 of 5 stars (1) Excellent
    St. Michaels
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
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    Location Information
    St. Michaels, Talbot County NA
    5 of 5 stars Reviewed 19 August 2014
    Location location location! Walk to perhaps the cutest town ever! Friendly people ,dog loving community, sail boats, restaurants and such a lovely little town.. Perfection found!
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    From
    $574
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    1 / 27
    4.5 of 5 stars (11) Very good
    Cambridge
    7 Bedrooms / 5 Bathrooms / Sleeps 18
    Overview Reviews (11) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    New premier waterfront vacation home - 6bed / 5bath home w/ beach & private pool. All of this on over 3 acres and +- 400 feet of stunning waterfront Near Cambridge Maryland, also Easton, St. Michaels and Oxford. The den also serves as an additional bdrm with full bath making it 7bdrms. Ideal... View all property information
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    Location Information
    Cambridge, Maryland 21613
    5 of 5 stars Reviewed 29 October 2014
    The Ideal Family Vacation This summer, our family decided to try something different and rent a house on the eastern shore of Maryland. After spending a day reconnoitering a...
    4 of 5 stars Reviewed 13 October 2014
    Really excellent location by the water, and the pool adds additional options. House itself is large, and is great for 2-3 families with kids. We were a group of friends, which...
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    From
    $243
    / Night
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    1 / 20
    5 of 5 stars (12) Excellent
    St. Michaels
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Reviews (12) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    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
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    Location Information
    St. Michaels, Talbot County 21663
    5 of 5 stars Reviewed 22 August 2014
    The pictures of this house do not lie. It is that nice. We parked our car and didn't need again until we left. Close to everything. Walk to the water , sit on the bench and...
    5 of 5 stars Reviewed 21 July 2014
    We fully enjoyed our relaxing stay in the sleepy little town of St. Michaels, and would definitely return when given the chance. The location is perfect - within a one block walk...
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    From
    $480
    / Night
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    1 / 22
    5 of 5 stars (1) Excellent
    St. Michaels
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
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    Location Information
    St. Michaels, Talbot County 21612
    From
    $461
    / Night
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    1 / 23
    5 of 5 stars (2) Excellent
    St. Michaels
    7 Bedrooms / 3 Bathrooms / Sleeps 11
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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
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    Location Information
    St. Michaels, Talbot County 21663
    5 of 5 stars Reviewed 27 September 2014
    Friends and family stayed at the home to watch my nephew get married on 9/20/14. I must say, the house was as much of the event as the wedding celebration. We went from 6 of us...
    5 of 5 stars Reviewed 24 July 2014
    Our daughter was married at the Tidewater Inn in Easton. We rented this lovely, large home the week before the wedding to have a place for the bride to relax while we spent time...
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    From
    $320
    / Night
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    1 / 5
    3 of 5 stars (1) Average
    Cambridge
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Charming, historic home in the Neck District, Maryland's most beautiful, unspoiled area. This adorable east-facing 100-year-old home sits on a generous lot (over an acre) with forever waterviews, mature shade trees, flowering perennials, roses, large fenced vegetable garden, breezy patio, wide... View all property information
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    Location Information
    Cambridge, Maryland 21613
    From
    $971
    / Night
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    1 / 38
    St. Michaels
    6 Bedrooms / 6 Bathrooms / Sleeps 12
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Walk to the attractions of St. Michaels, MD, yet private and quiet on a point of land with 500' shoreline, Bay Cottage is your home on the Chesapeake Bay with a relaxing waterside pol, private harbor and pier, organic culinary gardens, fruit farm, wellness studio, and warm hospitalities. There are... View all property information
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    Location Information
    St. Michaels, Talbot County 21663
    From
    $141
    / Night
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    1 / 34
    Greensboro
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Fishing...
    • Safe
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    HOME ON THE RIVER: A view of Choptank River (read James Michener's 'Chesapeake') from all rooms in cozy 2 bedroom apartment with full kitchen & bath. Separate entrance, patio, dock with canoe and kayaks. Peaceful setting within 2 miles of town and relatively close to Washington D.C., Baltimore.&... View all property information
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    Location Information
    Greensboro, Maryland 21639
    From
    $640
    / Night
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    1 / 18
    St. Michaels
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Fishing...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    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
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    Location Information
    St. Michaels, Talbot County 21653
    From
    $1,919
    / Night
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    1 / 7
    Oxford
    Studio / 4 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Fishing...
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Secluded, tranquil home located on the water, between Easton and Oxford, Maryland. Includes five bedrooms, four bathrooms, fully equipped kitchen, sun porch, swimming pool and tennis courts. Grounds include private driveway, miles of walking paths, and dock with two kayaks. View all property information
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    Location Information
    Oxford, Talbot County 21654
    From
    $320
    / Night
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    1 / 12
    Easton
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Exclusive 2 bedroom upstairs waterfront apartment with private entrance located 20 minutes from historic Easton and St. Michaels and 30 minutes from Oxford. Enjoy the sunrise each morning on your own private deck overlooking one of the most peaceful and unique surroundings the Eastern Shore has to... View all property information
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    Location Information
    Easton, Talbot County 21601
    From
    $358
    / Night
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    1 / 9
    St. Michaels
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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
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    Location Information
    St. Michaels, Talbot County 21662
    From
    $243
    / Night
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    1 / 40
    Cambridge
    3 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Hot Tub
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    'The Cottage' at Heron Cove is a cozy home situated on a scenic peninsula with water views from every window. Awake each morning to watch the sun glisten off the gentle waters. Explore ten acres of land and 1000 feet of shoreline. Relax on the wrap around screened in porch or soak in the 450 gallon... View all property information
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    Location Information
    Cambridge, Maryland 21613
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    From
    $1,095
    / Night
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    1 / 29
    Trappe
    8 Bedrooms / 6 Bathrooms / Sleeps 16
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Private Fishing...
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Martins Point is a late 18th Century house and cottages on Maryland's historic Eastern Shore where the Underground Railroad once passed through the property. It is located on a secluded finger of land, surrounded by water on three sides, a place to unwind, immerse yourself in the natural beauty of... View all property information
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    Location Information
    Trappe, Talbot County 21673