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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 39 Cottages in Preston with updated reviews, rates, and availability.

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, (181)
"Host was amazing. Property is perfect. Will be staying here again. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Marina

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (118)
"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
Property grounds

Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills

Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (247)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Property grounds

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

9.6 out of 10, Exceptional, (138)
"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
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Miscellaneous

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

10.0 out of 10, Exceptional, (9)
"The home was so well appointed and walking distance to stores, restaurants, quaint museums and beautiful nature. The host was so friendly and helpful with quick responses. We had high winds and lots of rain, but stayed cozy and warm. What a friendly Island of people!!"
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Waterfront property with private boat ramp and new dock!
Outdoor dining

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!
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!
Beach towels

Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

10.0 out of 10, Exceptional, (88)
"Beautiful property in a great location!"
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!
Eastern Shore Waterside Cottage Near St. Michaels
Outdoor dining

Eastern Shore Waterside Cottage Near St. Michaels

10.0 out of 10, Exceptional, (19)
"Really enjoyed our stay, pool was nice and had plenty of amenities. We will definitely be coming back for another stay."
Eastern Shore Waterside Cottage Near St. Michaels
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Property grounds

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

10.0 out of 10, Exceptional, (4)
"A few local spots to eat were great in the morning especially the Tighlman Market! Market has all you need to stock up with groceries and is just 2 minutes from the house."
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Waterfront, cozy cottage with private pool on 27 acres
Beach nearby

Waterfront, cozy cottage with private pool on 27 acres

9.8 out of 10, Exceptional, (88)
"Great property and the owners were gracious hosts."
Waterfront, cozy cottage with private pool on 27 acres
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (116)
"Perfect stay in a historic home in the heart of town."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Charming Waterfront Cottage Retreat near St. Michaels
Fridge, microwave, oven, stovetop

Charming Waterfront Cottage Retreat near St. Michaels

10.0 out of 10, Exceptional, (4)
"Great weekend get away if you’re just looking for some peace and quiet with some great scenery. The kitchen was immaculate and everything was as listed."
Charming Waterfront Cottage Retreat near St. Michaels
Cottage at Goose Neck Point
Sun loungers, beach towels

Cottage at Goose Neck Point

10.0 out of 10, Exceptional, (32)
"Quite and enjoyable with easy access to a multitude of fabulous restaurants, and outdoor fun. "
Cottage at Goose Neck Point
Private waterfront cottage with pool on Church Creek
Fridge, microwave, oven, stovetop

Private waterfront cottage with pool on Church Creek

10.0 out of 10, Exceptional, (61)
"Very clean, comfortable, and cozy property with gorgeous view of the water. Would definitely stay here again. Just wish we spent more time on the property this stay, but obligations in Fishing Creek kept us away most of the time. Thank you for sharing your lovely cottage!!"
Private waterfront cottage with pool on Church Creek
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Property grounds

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)
Tilghman Island Retreat By Knapps Narrows!
Interior

Tilghman Island Retreat By Knapps Narrows!

3.0 star property
Tilghman Island Retreat By Knapps Narrows!
Grasonville Home w/ Private Pool on the Water
Interior

Grasonville Home w/ Private Pool on the Water

3.0 star property
Grasonville Home w/ Private Pool on the Water
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
House (4 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

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
Miscellaneous

Beautiful Colonial Home on the Choptank River

3.0 star property
Beautiful Colonial Home on the Choptank River
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

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, (8)
"This stay was perfect. The location was charming and safe, and the home was clean and cozy. Jennifer was a very accommodating and responsive host."
The price is AED 771
AED 1,553 total
includes taxes & fees
29 May - 30 May
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
The heart of St Michaels awaits.
Exterior

The heart of St Michaels awaits.

10.0 out of 10, Exceptional, (37)
"This flat/apartment is perfect, exactly as described. Located in the heart of town, convenient to all restaurants and shops. The flat beautifully updated and appointed, and spotlessly clean. We were extremely comfortable and will definitely return."
The heart of St Michaels awaits.
Beautiful Waterfront Retreat in Cambridge!
Fridge, microwave, oven, stovetop

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (34)
"The house was so cute and the fact that we were able to do early check in was amazing!"
The price is AED 1,010
AED 1,861 total
includes taxes & fees
8 Jun - 9 Jun
Beautiful Waterfront Retreat in Cambridge!
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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