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Compare 172 Vacation Homes in Preston with updated reviews, rates, and availability.

Walk to Everything House
Front of House

Walk to Everything House

10.0 out of 10, Exceptional, (72)
"We thoroughly enjoyed the convenience of walking to shops, restaurants, and waterfront! Residence was charming and clean! Only minor issue was we couldn’t locate the iron- just the ironing board! We still had fun but we’re just a bit wrinkled!😁"
Walk to Everything House
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
Nature,Outdoors,Scenery,Water,Waterfront

Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

10.0 out of 10, Exceptional, (4)
"We had the most wonderful time at this charming house on Tillman Island! While the pics are great, it is even better in person. The house is perfectly nestled on the waterway, offering stunning views. The backyard pool was a true highlight, and we spent countless hours splashing around, the pool in the sun."
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Cambridge Vacation Rental | 7BR | 5.5BA | Stairs Required | 10,333 Sq Ft

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

9.6 out of 10, Exceptional, (17)
" October 11-14, 2024, we rented the “Willoughby” for a family reunion. Let me start out by saying this home is amazing. It looks exactly as pictured based on the website photos. It was even better than I expected. If you are considering this property, I highly recommend booking it! Believe me when I say the Willoughby is a rare gem. The location of the home is perfect and extremely private. The grounds are pristine and the view of the water is breathtaking. The home sits on the Hudson...
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Luxury on the river, steps to downtown &boat ramp!
Exterior

Luxury on the river, steps to downtown &boat ramp!

10.0 out of 10, Exceptional, (5)
"Stayed for three nights with a few friends with a focus on birding. The house is in a great location for "
The price is AED 797
AED 1,620 total
includes taxes & fees
2 Dec - 3 Dec
Luxury on the river, steps to downtown &boat ramp!
Beautiful Peaceful Home
Living area

Beautiful Peaceful Home

7.4 out of 10, Good, (3)
"Owner canceled the day before with no notice"
Beautiful Peaceful Home
Travelers Rest Spacious 5BR Pool riverfront Pier charming Easton Saint Michaels
Miscellaneous

Travelers Rest Spacious 5BR Pool riverfront Pier charming Easton Saint Michaels

2.0 star property
10.0 out of 10, Exceptional, (1)
"We would love to return to Travelers Rest! Spacious home with separate master suites, waterfront views, large efficient kitchen, large private property, fairly isolated and within easy striking distance to Easton and St Michaels. We’ve rented many homes in this area and Travelers Rest is among the best. "
Travelers Rest Spacious 5BR Pool riverfront Pier charming Easton Saint Michaels
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Living Area

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (32)
"Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Exterior

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

10.0 out of 10, Exceptional, (32)
"Perfect large space on a quiet and pretty area. Really great space. "
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Aerial view

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

10.0 out of 10, Exceptional, (7)
"This house is huge and has lots of different indoor and outdoor gathering spaces so the kids and adults in our group of three families didn’t have to be on top of each other in one living space the whole time. Big firepit area and huge lawn were great, and we enjoyed the kayaks and canoe. There’s a place to buy fresh crabs, oysters, and shrimp very close by, and the house has everything you need for a crab night. The owner was incredibly responsive and kind."
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Waterfront Getaway with Dock
Property grounds

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (37)
"Every morning I made coffee, lit the fire pit on the dock and spent at least from 30 minutes before sunrise to 30 after. Used Merlin to identify bird calls. Heard and saw bald eagles, a belted kingfisher and an eastern bluebird. Watched a great blue heron fishing. Heard many many different birds. Truly an awesome location to slow down and enjoy the moment "
The price is AED 845
AED 1,024 total
includes taxes & fees
15 Dec - 16 Dec
Waterfront Getaway with Dock
Cottage on Cabin Creek
Beach

Cottage on Cabin Creek

10.0 out of 10, Exceptional, (100)
"I highly recommend staying here for a cozy couples weekend. It was absolutely beautiful and quiet. The host was so nice and made us feel welcome. I can’t wait to stay here again."
The price is AED 918
AED 1,332 total
includes taxes & fees
11 Dec - 12 Dec
Cottage on Cabin Creek
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
Aerial view of property- river, dock, pergola , pool behind house

Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks

9.8 out of 10, Exceptional, (6)
"We enjoyed our time at the house very much. We went out to dinner only once and the rest of the time we ate in. We grilled two nights and made a roast one night. The views and the pool were more than you could imagine."
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
Pool

Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!

9.8 out of 10, Exceptional, (9)
"Our stay was amazing. The house is beautiful. The views and peaceful location were completely used. We had many fun game nights and dinners around the table, the kitchen easily provided many happy meals. The gas grill, the fire pit were easy to use. The kayaks were a lot of fun. Sitting on the dock enjoying the peaceful quiet mornings was rejuvenating. The pool chairs and umbrellas were really nice. A ping pong table in the garage was a ton of fun too. The extra fridge/freezer was handy and the...
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
Autumn Charm Beautiful Waterfront Retreat Near Historic St. Michaels & Royal Oak
Property grounds

Autumn Charm Beautiful Waterfront Retreat Near Historic St. Michaels & Royal Oak

9.8 out of 10, Exceptional, (37)
"Great rental experience. Barb was fantastic at communicating. The house was perfect for our group, including some adults and some young children. Yard and dock were a blast for playing and fishing. "
Autumn Charm Beautiful Waterfront Retreat Near Historic St. Michaels & Royal Oak
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub
View

Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub

10.0 out of 10, Exceptional, (3)
"8 of us had a great time on Harris Creek in McDaniel, MD. Pulled our boats up to private dock and crabbing in minutes. "
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock
Pool

Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock
Heated pool, sandy beach, pier, and playground set punch point apart!
Exterior

Heated pool, sandy beach, pier, and playground set punch point apart!

10.0 out of 10, Exceptional, (3)
"We had a wonderful and serene stay. We were traveling with our 9 month old and the play mat and toy area were so convenient. The renter also provided a crib and high chair. It’s an amazing home and view. "
Heated pool, sandy beach, pier, and playground set punch point apart!
Cozy 2BR Home near Idlewild Park
Living area

Cozy 2BR Home near Idlewild Park

10.0 out of 10, Exceptional, (2)
"This property was in a great location for attending the Waterfowl festival. The host thought about each detail and our stay was more than comfortable. "
Cozy 2BR Home near Idlewild Park
Relaxing, spacious 5BR house on the Hudson Creek in charming Cambridge
Room

Relaxing, spacious 5BR house on the Hudson Creek in charming Cambridge

2.0 star property
The price is AED 441
AED 1,643 total
includes taxes & fees
27 Nov - 28 Nov
Relaxing, spacious 5BR house on the Hudson Creek in charming Cambridge
4 bdrm, 3 bath, 2,700 sqft house on 1 acre with chickens and fenced in back yard
Living area

4 bdrm, 3 bath, 2,700 sqft house on 1 acre with chickens and fenced in back yard

2.0 star property
4 bdrm, 3 bath, 2,700 sqft house on 1 acre with chickens and fenced in back yard
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

Relaxing Waterfront Cottage Near St Michaels, Maryland
Charming Cottage on a quite creek of the Chesapeake Bay with private pool.

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (217)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
Walk to Everything House
Front of House

Walk to Everything House

10.0 out of 10, Exceptional, (72)
"We thoroughly enjoyed the convenience of walking to shops, restaurants, and waterfront! Residence was charming and clean! Only minor issue was we couldn’t locate the iron- just the ironing board! We still had fun but we’re just a bit wrinkled!😁"
Walk to Everything House
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
Nature,Outdoors,Scenery,Water,Waterfront

Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

10.0 out of 10, Exceptional, (4)
"We had the most wonderful time at this charming house on Tillman Island! While the pics are great, it is even better in person. The house is perfectly nestled on the waterway, offering stunning views. The backyard pool was a true highlight, and we spent countless hours splashing around, the pool in the sun."
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
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.