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Compare 32 Cottages in Preston with updated reviews, rates, and availability.

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, (212)
"As always our stay was amazing from kayaking, bird watching, sunsets. The cove is a special place."
Relaxing Waterfront Cottage Near St Michaels, Maryland
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Front of house from St. Michaels harbor looking across Town Park
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (107)
"We love staying at the John Bruff house in St. Michaels. The location is great, right in the heart of town! Our family has been staying here for the past few years and we can’t wait to go back!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Front of Carpenter St. Cottage
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (165)
"Great little cottage and plenty of space for our family of 3 to have an end-of-Summer getaway to one of our favorite towns. Prompt and easy communication with the owner, Tom, both before and during our stay. We loved the back porch and were blessed with some cooler temps and were able to enjoy sitting out there. FYI - Den has a door (third bedroom with pull out sofa). We have rented on Carpenter Street before, and the location cannot be beat as far as walkability to everything in town and along...
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Eastern Shore Waterside Cottage Near St. Michaels
wrap around porch with rockers and dining area
Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, (18)
"Wonderful property in a beautiful setting. We had a lovely weekend with family. Would highly recommend the property!"
Eastern Shore Waterside Cottage Near St. Michaels
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Blue heron sunset
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
10.0 out of 10, Exceptional, (6)
"Our stay was amazing! Words cannot say enough! The view is magical. We enjoyed coffee on the porch to watch the sunrise and the crab/oyster boats going in and out. Maria, is a wonderful and very thoughtful host. At her recommendation, we went to the free wine tasting at the General Store at the end of the street. We met several local residents who could not be more kind and fun to talk with. We can't wait to come back and stay again."
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Cozy retreat in peaceful wooded setting. Pet friendly!
Path to cottage
Cozy retreat in peaceful wooded setting. Pet friendly!
2.0 star property
10.0 out of 10, Exceptional, (1)
"Private country setting with a short drive to civilization. Small studio style home easy to get around with open setting. Owners are super friendly and easy to communicate with"
Cozy retreat in peaceful wooded setting. Pet friendly!
Waterfront, cozy cottage with private pool on 27 acres
Private Pool
Waterfront, cozy cottage with private pool on 27 acres
9.8 out of 10, Exceptional, (87)
"We had a wonderful time overlooking the water and swimming in the refreshing pool while enjoying easy access to downtown Cambridge and Blackwater NW Refuge."
Waterfront, cozy cottage with private pool on 27 acres
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Front and side view of Blades House from Locust St.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (130)
"Had a wonderful time. This home was just perfect for us. Great location and charming. Would definitely stay here again"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Cottage at Goose Neck Point
Living area
Cottage at Goose Neck Point
10.0 out of 10, Exceptional, (28)
"What a little slice of heaven. Checkin was easy peasy. Owner left a welcome basket w goodies and wine. That was a very nice gesture. The property and area is beautiful. I wish I could call it my home away from home:). The home was perfect, clean and everything the pictures showed. Just a perfect getaway to escape the craziness of life. Didn’t want to leave. "
Cottage at Goose Neck Point
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Front and side of W Melson House
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (114)
"Waters edge is just a few steps away to sit and watch boats come in and out. So cute and the most amazing artifacts decorating the place made it even more captivating. Short walk to coffee, food and shopping local. The owner was responsive and kind as well as super easy to work with. Will definitely return."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
The Middle Point Cabin in Saint Michaels
Living area
The Middle Point Cabin in Saint Michaels
9.8 out of 10, Exceptional, (48)
"nice property. secluded. clean and comfortable. owners very very responsive. "
The Middle Point Cabin in Saint Michaels
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
10.0 out of 10, Exceptional, (1)
"This was an amazing property. Very clean and very cute and cozy. Beautiful property. The owners were fantastic. Very responsive and caring. Loved it! Would definitely return."
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
-A travelers cottage - A place to rest after a busy day.
Exterior
-A travelers cottage - A place to rest after a busy day.
10.0 out of 10, Exceptional, (25)
"We wanted a place not far from parks along the bay and this place fit our needs perfectly."
-A travelers cottage - A place to rest after a busy day.
Artists, writers & creative minds stay and BE INSPIRED AT SIMPLICITY COTTAGE
Exterior
Artists, writers & creative minds stay and BE INSPIRED AT SIMPLICITY COTTAGE
10.0 out of 10, Exceptional, (1)
"If you want to get away from it all, this is the place to be. My wife and I celebrated our 20th wedding Anniversary. Calm and peaceful, nestled right by the Choptank River. The cottage itself was very comfortable. The air conditioner worked great. It was a pleasure staying there and we will probably return next year."
Artists, writers & creative minds stay and BE INSPIRED AT SIMPLICITY COTTAGE
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Exterior
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
3.0 star property
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Grasonville Home w/ Private Pool on the Water
Pool
Grasonville Home w/ Private Pool on the Water
3.0 star property
Grasonville Home w/ Private Pool on the Water
Waterfront Retreat < 4 Mi to Dtwn Cambridge!
Property grounds
Waterfront Retreat < 4 Mi to Dtwn Cambridge!
3.0 star property
Waterfront Retreat < 4 Mi to Dtwn Cambridge!
Beautiful Colonial Home on the Choptank River
Exterior
Beautiful Colonial Home on the Choptank River
3.0 star property
Beautiful Colonial Home on the Choptank River
Pet-friendly Cambridge Home - Walk to River!
Living area
Pet-friendly Cambridge Home - Walk to River!
3.0 star property
Pet-friendly Cambridge Home - Walk to River!
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Property grounds
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
3.0 star property
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
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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, (212)
"As always our stay was amazing from kayaking, bird watching, sunsets. The cove is a special place."
Relaxing Waterfront Cottage Near St Michaels, Maryland
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Our home blends into towering pines, lawns & hundreds of feet of waterfront
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, (71)
"We stayed at Saddle House during 2024 Ironman Maryland, with 2 Ironmans competing and lots of support traveling to stay. I was concerned choosing a house about 20 minutes from the start/finish but it was an amazing choice with great bike route access. House is secluded and serene, amazing cleanliness, kitchen with everything you could ever need. Pictures are very accurate to the product you get. Jon was a great help finding things to do, house has incredible resources that support you during...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Enjoy the sunset from Long Wharf Marina across the street
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
10.0 out of 10, Exceptional, (4)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is SAR 675
SAR 1,495 total
includes taxes & fees
22 Oct - 23 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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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