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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

Compare 165 Vacation Homes in Preston with updated reviews, rates, and availability.

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Outdoor pool

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

10.0 out of 10, Exceptional, (85)
"Gorgeous views and surroundings"
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Grasonville Home w/ Private Pool on the Water
Pool

Grasonville Home w/ Private Pool on the Water

9.8 out of 10, Exceptional, (20)
"We started an annual tradition to rent this house with friends. Love the property, beautiful views and great location. Making great memories that will last a lifetime. Thank you for allowing us to use your beautiful home! :)"
Grasonville Home w/ Private Pool on the Water
Time Stands Still At the Dock.
Outdoor dining

Time Stands Still At the Dock.

10.0 out of 10, Exceptional, (2)
"What a wonderful experience! A relaxing time with an amazing view! Thank you Jennifer"
Time Stands Still At the Dock.
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
Exterior

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

9.8 out of 10, Exceptional, (40)
"Our group of longtime friends from different states wanted a convenient location to meet for a weekend getaway. The Eastern Shore was a good location and this property was a wonderful and comfortable place for our group. The house was spacious and had plenty of areas for members of the group to enjoy all together or in smaller conversation groups. Our group meals were easy to prepare in the large and well-equipped kitchen. The dining room easily accommodated our group for our dinners and the...
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
Waterfront Getaway with Dock
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (38)
"Stayed at the rental for a day sandwiched between two nights. Perfect for R&R. "
The price is AED 845
AED 1,020 total
includes taxes & fees
7 Mar - 8 Mar
Waterfront Getaway with Dock
Luxury Waterfront Retreat with in ground pool and close to town
Miscellaneous

Luxury Waterfront Retreat with in ground pool and close to town

10.0 out of 10, Exceptional, (34)
"12 of my friends and i stayed here for my birthday, not only did the hosts leave me a nice birthday gift, but a wonderful place to hang out for a weekend. The place is immaculate and well thought out. They paid attention to every detail! The kitchen is fully stocked so that we could cook for and feed all 13 of us. The entire weekend people kept telling me it was so comfortable, so clean, surprisingly well stocked, beautiful, fun to be in, etc.! Will definitely return! Mindy was very responsive...
Luxury Waterfront Retreat with in ground pool and close to town
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Interior

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

2.0 star property
9.6 out of 10, Exceptional, (4)
"Very clean, well stocked with towels, paper products and everything else you need. Lots of space for a large group. I liked the master bedroom on the first floor. Having a second coffee maker upstairs is a nice touch. Walking distance to downtown. "
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Fridge, microwave, stovetop, dishwasher

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

9.6 out of 10, Exceptional, (21)
"Very large nicely appointed house with lots of space for large groups. Unfortunately the pool heater was out of service but they gave us a rebate for the inconvenience. One major deficiency is the internet/WIFI with is satellite and somewhat slow and dropped frequently . If you need streaming for work or other activities you might be frustrated."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Minutes from Downtown Cambridge | Private Dock | Pool | Kayaks
Smart TV, fireplace, video games, DVD player

Minutes from Downtown Cambridge | Private Dock | Pool | Kayaks

9.4 out of 10, Exceptional, (16)
"Very well equipped home at a beautiful location overlooking the water. The pool was a real treat for the kids in our group. The property manager was in regular communication and quickly dealt with one item that needed attention."
Minutes from Downtown Cambridge | Private Dock | Pool | Kayaks
Walk to Everything House
Fridge, microwave, oven, stovetop

Walk to Everything House

10.0 out of 10, Exceptional, (76)
"Clean and nice place to stay"
Walk to Everything House
Gorgeous Creek Side Ranch-Style Estate With Dock
Fridge, microwave, oven, stovetop

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (6)
"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "
Gorgeous Creek Side Ranch-Style Estate With Dock
Modern Family Retreat – Roomy, Chic, and Close to DE Turf, Casino & the Beaches!
Fridge, microwave, oven, stovetop

Modern Family Retreat – Roomy, Chic, and Close to DE Turf, Casino & the Beaches!

The price is AED 1,102
AED 1,408 total
includes taxes & fees
31 Mar - 1 Apr
Modern Family Retreat – Roomy, Chic, and Close to DE Turf, Casino & the Beaches!
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*
Terrace/patio

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

10.0 out of 10, Exceptional, (55)
"The family had a lovely time. The home was beautiful and the landscape surrounding the home was magnificent. "
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Property grounds

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

10.0 out of 10, Exceptional, (7)
"The Lighthouse cottage was super clean & comfortable, beautifully decorated and stocked with supplies, and located on a lovely block overlooking water l. As a bonus, it was walking distance from downtown’s many shops and restaurants. "
The price is AED 514
AED 1,257 total
includes taxes & fees
9 Mar - 10 Mar
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf
Property grounds

Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

9.6 out of 10, Exceptional, (5)
"The owners made sure the driveway was shoveled and left us a seashell!"
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf
Serene Waterfront Minutes from St Michaels.
Terrace/patio

Serene Waterfront Minutes from St Michaels.

9.8 out of 10, Exceptional, (7)
"We truly loved our stay! The home was super comfortable and well stocked for making Thanksgiving dinner for 6. We loved just looking out at the geese, swans and blue herons ! Really lovely. We’ll be back!"
Serene Waterfront Minutes from St Michaels.
Stylish Home on the Choptank River (with Tidal Beach)
Property grounds

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (32)
"A beautiful and serene setting mapping the contours of nature, tranquility & relaxation. Steven is an exceptional host."
Stylish Home on the Choptank River (with Tidal Beach)
Tilghman Island Retreat By Knapps Narrows!
TV, books

Tilghman Island Retreat By Knapps Narrows!

2.0 star property
Tilghman Island Retreat By Knapps Narrows!
Sunset Breezes - quiet waterfront retreat
Property grounds

Sunset Breezes - quiet waterfront retreat

10.0 out of 10, Exceptional, (35)
"Great "
Sunset Breezes - quiet waterfront retreat
Downtown Oxford | Charming | Pet Friendly
Exterior

Downtown Oxford | Charming | Pet Friendly

9.8 out of 10, Exceptional, (38)
"A lovely quaint Oxford home in a great location. Quiet, with views of the Harbor and the Tred Avon River from the street. A first floor bedroom and 2 upstairs, make it possible to include older parents in a family stay. To relax together with coffee in the morning and share wine porch side in the afternoon is an experience that no hotel can duplicate."
Downtown Oxford | Charming | Pet Friendly
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Preston

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Outdoor pool

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

10.0 out of 10, Exceptional, (85)
"Gorgeous views and surroundings"
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Outdoor dining

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (173)
"Great location! Antique furniture in a well maintained beautiful old house. Exactly what we needed."
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (220)
"This was a winter getaway to a very comfortable house with all the amenities on a quiet tributary of the Chesapeake. A rare vacation for and just what we wanted. Conveniently located near St Michael’s and Easton. Communication was excellent and everything was just as described. Would go back if we get the opportunity. "
Relaxing Waterfront Cottage Near St Michaels, Maryland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.