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Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Compare 29 Cottages in Preston with updated reviews, rates, and availability.

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, (113)
"The location couldn't have been more ideal. We were able to walk everywhere...all around town. And there was a beautiful view of the town park and the bay from the house. We were there for Christmas, visiting family, and her house was overflowing, so this was a little home-away-from-home. There were some difficulties. The shower curtain and main bath downstairs needs updating and the kitchen could be better appointed. The stairs to the king bed bedroom are, as others and the owner noted, very...
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, (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
"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, (7)
"“Point of View” waterfront cottage did not disappoint. In fact, it was beyond expectations. Maria’s (the host) personal touches made the cottage feel like home. We used “Point of View” as overflow for a family reunion we were having. It is perfectly situated for easy walking to anything you need or want to do on Tilghman Island. The views from the cottage are amazing. Being on the entrance to Dogwood Harbor provides you with a real time experience of what a waterman’s life is truly all...
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
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, (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
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, (116)
"This was a quick getaway for my husband, me, and our 2-year-old grandson. The location of this property is perfect! We could walk over to the waterfront and watch the geese or walk into town for shopping and food. We lost power (a fluke) during our stay, and the owner was extremely responsive and easy to contact. We walked to dinner, and it was back on when we returned. Highly recommend!"
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
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, (19)
"Had a great visit. House was perfect and the area is absolutely gorgeous"
Eastern Shore Waterside Cottage Near St. Michaels
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, (136)
"We loved this house, it was perfect for exploring town and as a base for things further afield. Comfortable, thoughtfully and well stocked with lots of charm."
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
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
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
Waterfront property with private boat ramp and new dock!
Exterior

Waterfront property with private boat ramp and new dock!

9.6 out of 10, Exceptional, (8)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!
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, (2)
"Great little cottage, beautiful scenery, quiet and peaceful. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cottage at Goose Neck Point
Living area

Cottage at Goose Neck Point

10.0 out of 10, Exceptional, (31)
"We loved everything about this sweet cottage on the water! The decor was top notch, and so welcoming! We stayed 3 nights, and can’t say enough about this beautiful area of Maryland. Great restaurants, shoppes, and delicious crabs! We also did the ferry ride over to Oxford. Had an amazing time at this property! The host also left some yummy treats, and a bottle of champagne for our anniversary! Can’t wait to come back!"
Cottage at Goose Neck Point
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!
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Exterior

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (2)
"Quiet, peaceful, relaxing!"
Artists, writers & creative minds IMAGINE YOUR GETAWAY 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!
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
Charming Waterfront Cottage Retreat near St. Michaels
Exterior

Charming Waterfront Cottage Retreat near St. Michaels

10.0 out of 10, Exceptional, (1)
"Our stay at this beautiful cottage was truly unforgettable! The space was clean, cozy, and well-appointed, with every detail carefully considered. Nestled right on the water’s edge, every inch of the house was tastefully decorated and had all the amenities you could ask for. The tasteful decor, fully stocked kitchen, and comfortable bed made us feel right at home from the moment we arrived.The hosts went above and beyond to make this an enjoyable stay, with excellent communication and thoughtful...
Charming Waterfront Cottage Retreat near St. Michaels
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!
Family-friendly Cambridge Home w/ Fire Pit!
Terrace/patio

Family-friendly Cambridge Home w/ Fire Pit!

3.0 star property
Family-friendly Cambridge Home w/ Fire Pit!
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

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, (113)
"The location couldn't have been more ideal. We were able to walk everywhere...all around town. And there was a beautiful view of the town park and the bay from the house. We were there for Christmas, visiting family, and her house was overflowing, so this was a little home-away-from-home. There were some difficulties. The shower curtain and main bath downstairs needs updating and the kitchen could be better appointed. The stairs to the king bed bedroom are, as others and the owner noted, very...
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Exterior

Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

9.6 out of 10, Exceptional, (19)
"The house was just as it was listed!! Our annual family vacation was so much fun here! Plenty of room, very clean, and fully stocked! Peddle boats, kayaks, and pool used daily!! Fire every night!!! Thank you for the wonderful hospitality!!!"
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Walk to Everything House
Front of House

Walk to Everything House

10.0 out of 10, Exceptional, (76)
"Clean and nice place to stay"
Walk to Everything House
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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