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Compare 185 Vacation Homes in Trappe with updated reviews, rates, and availability.

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (27)
"The house was perfect for our needs. It has a cute, fenced in yard so our 2 dogs could hang outside. It had everything we needed for a wonderful weekend birthday celebration!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (4)
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Newly Remodeled Home, 10 Minute Walk to Downtown
10.0 out of 10, Exceptional, (5)
"Very clean house with comfortable beds. Enjoyed our stay!"
Newly Remodeled Home, 10 Minute Walk to Downtown
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Grace Cottage, Saint Michaels Walk to everything!
10.0 out of 10, Exceptional, (1)
"Beautiful house. Great location. Host was very responsive to questions. Thanks for a great stay"
Grace Cottage, Saint Michaels Walk to everything!
Hudson Creek Retreat, 5 Acre Waterfront Home, Pool, Pier, Fishing & Crabbing
Hudson Creek Retreat, 5 Acre Waterfront Home, Pool, Pier, Fishing & Crabbing
Peaceful Queenstown Home w/ Deck & Grill!
8.0 out of 10, Very Good, (1)
"The home was clean and lovely."
Peaceful Queenstown Home w/ Deck & Grill!
Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Michaels / Easton
9.6 out of 10, Exceptional, (66)
"we had a business trip up in MD - had 8 guys up there with the owner of the company and everyone was very comfortable. The rental property let us know that the pool was closed, but it all worked out great cause the weather was awful. The property/house was fantastic for the 8 of us. Space wise and sleeping it was perfect. Thank you."
Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Michaels / Easton
365-degree waterfront views. Quiet property bordering Blackwater River Refuge.
10.0 out of 10, Exceptional, (2)
"This house is a big surprise for our group, everyone loves it and really enjoyed the trip. All-around water view, th house is spacious with 8 bedrooms, well-decorated and equipped (lots of kitchen gadgets). The host is super easy to communicate as well. Kids had fun time crabbing. Will definitely come back."
365-degree waterfront views. Quiet property bordering Blackwater River Refuge.
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
The price is AED 1,833
AED 3,107 total
includes taxes & fees
10 Jun - 11 Jun
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (17)
"We enjoyed our trip, the house was fully equipped and had all the comforts you could need. The water view, watching the birds, the kayak, the dock at sunrise, were our favorite things. We look forward to coming back sometime soon."
The price is AED 1,073
AED 1,857 total
includes taxes & fees
16 Jun - 17 Jun
Beautiful Waterfront Retreat in Cambridge!
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
10.0 out of 10, Exceptional, (31)
"One of the best properties I have stayed at. With all the amenities, you never need to leave the home. We enjoyed the views, the quietness of the area, and the wildlife. We nicknamed two beautiful ducks…Sonny and Cher! The house is very clean, the checkin checkout procedures were very easy. The host communicated all the details plus additional suggestions. We are definitely returning very soon."
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
10.0 out of 10, Exceptional, (5)
"We had a lovely stay at The Blue Heron. We had a retreat scheduled with friends that we had to relocate last minute due to snow in western Maryland. We stumbled upon this listing, and the home was perfect for our needs. Plenty of beds, fully stocked kitchen, several rooms and couches for those who wanted to read, others to play games, and others to watch football playoffs on tv. The best part of the house was the dining room table that could seat up to 18 (?). It was nice to be able to not have...
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
9.6 out of 10, Exceptional, (4)
"Nice place for a getaway."
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
Grasonville Home w/ Private Pool on the Water
10.0 out of 10, Exceptional, (14)
"We had a wonderful time in Grasonville. The property was very clean and well maintained. Views from the home were serene as most rooms have views of the water which we absolutely loved. Another perk of the home is its proximity to surrounding attractions. Our group felt like we were secluded enough but could easily get something in town if needed. We didn’t need much since the home was well stocked. When we contacted the host about a question, they responded quickly. We would definitely stay...
Grasonville Home w/ Private Pool on the Water
Thorneton Point Estate
9.8 out of 10, Exceptional, (6)
"We had a great time. The pool was a big hit and all the common areas in the house gave us plenty of room to spread out. The game room was super, also. A few things that would make it even greater: about half a dozen cockroaches and other bugs were found in the house; lack of instruction manuals for appliances and sauna; exterior doors very difficult to lack; comforter in bedroom 1 smelled like dogs. Matt was very helpful and responsive to questions"
Thorneton Point Estate
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub
10.0 out of 10, Exceptional, (1)
"This is a great property. It was comfortable, clean and spacious. The amenities of bikes and kayaks and a canoe made our stay very enjoyable. Close to downtown St. Michaels but on a quiet inlet. We really enjoyed our stay. Management company was readily available and highly responsive as well."
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub
Stylish Home on the Choptank River (with Tidal Beach)
10.0 out of 10, Exceptional, (25)
"The home is clean, comfortable, and has a gorgeous outdoor living space right on the water. We even had my son's wedding day party prep photos taken here. We would definitely stay here again."
Stylish Home on the Choptank River (with Tidal Beach)
Downtown St. Michaels | Bikes | Kayaks | Private Pier
9.8 out of 10, Exceptional, (20)
"Very clean and large property on scenic river. Only disappointing issues included problems launching kayaks over a tall wall and unfriendly TY cable system. Offset by abundance of great restaurants and peaceful and well maintained home."
Downtown St. Michaels | Bikes | Kayaks | Private Pier
Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock
10.0 out of 10, Exceptional, (4)
"It was great! We loved it and would come back. Fyi - we did run out of TP, gas for grill and dishwasher soap."
Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private 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.

Other property types in Trappe

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (4)
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (105)
"This is our third visit. You can’t have a better location! We love St. Michael’s and this historical cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Walk to Everything House
10.0 out of 10, Exceptional, (64)
"The house was perfectly located in town in St. Michael’s with off street parking as a bonus. Despite the weather being cold and rainy, we had a lovely time in charming St. Michaels. It was a delightful spot for our annual girls weekend."
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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