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

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

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

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

9.6 out of 10, Exceptional, (136)
"The T. Blades house was the perfect choice for a two day quick getaway for my husband and I. The house is not only filled with period charm and character, but has been lovingly and perfectly restored to make it a very comfortable stay. Immaculately clean and furnished. The location is a 5 star, as well. One block to the main street with shops and restaurants, and two blocks in the other direction to the water. Can't wait to go back. Kathleen and John"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

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

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

10.0 out of 10, Exceptional, (8)
"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

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (242)
"If you’re looking for a remote location on the water, this is it. House was clean, hosts were nice. No complaints. "
Family and Pet-Friendly, Waterfront with Pier

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!

10.0 out of 10, Exceptional, (88)
"Wonderful. "
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
10.0 out of 10, Exceptional, (6)
"This VRBO was very clean. Since it is a fairly new addition to VRBO, we thought it could use a little more info, like a portfolio with the combination to the bike locks, where to go to eat and visit, etc. Also, the only coffeemaker was a Keurig and we didn’t bring any K-cups. The 4 of us had a nice 50th Anniversary long weekend."
The price is AED 1,539
AED 3,309 total
includes taxes & fees
7 Mar - 8 Mar
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

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!

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

9.6 out of 10, Exceptional, (117)
"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

Private waterfront cottage with pool on Church Creek

10.0 out of 10, Exceptional, (61)
"This was one of the most beautiful spots I've seen. Kayaking was wonderful! Couch was very uncomfortable. And many maybe put off to find they must put everything in a box to keep away from rodents. And I just took my garbage home as we didn't have time to dump at an off site location on vacation. I would still book again as it was the most peaceful, charming and secluded place to truly relax!"
Private waterfront cottage with pool on Church Creek

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

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

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)

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

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

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

3.0 star property
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Bayfront Gem w/ Amazing Water Views + Pond!

3.0 star property
Bayfront Gem w/ Amazing Water Views + Pond!
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 Trappe

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

10.0 out of 10, Exceptional, (4)
"Really comfortable home in a quiet neighborhood! All of the beds are comfortable, the laundry was convenient and the grounds are lovely. The managers have been easy to work with. We'll be back!"
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

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

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
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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