Trappe Vacation Rentals

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Browse Select Trappe Vacation Homes

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, 26 reviews
"The stay was a perfect location for doing things in downtown St. Michael's, everything is within walking distance. The property managers were prompt with all communications and pleasant to work with on a few questions I had."
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, 4 reviews
"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!
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
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Cambridge Beach Home on Choptank River w/ Pier!
10.0 out of 10, Exceptional, 12 reviews
"This place was perfect for our group of 9. Super well equipped. There wasn't a single thing we needed that it didn't have. Lovely!"
Cambridge Beach Home on Choptank River w/ Pier!
Newly Remodeled Home, 10 Minute Walk to Downtown
10.0 out of 10, Exceptional, 4 reviews
"Very clean house with comfortable beds. Enjoyed our stay!"
Newly Remodeled Home, 10 Minute Walk to Downtown
Grace Cottage, Saint Michaels Walk to everything!
10.0 out of 10, Exceptional, 1 review
"Beautiful house. Great location. Host was very responsive to questions. Thanks for a great stay"
Grace Cottage, Saint Michaels Walk to everything!
Charming 3-bedroom Midcentury modern home, retro vibe and stylish furnishings.
10.0 out of 10, Exceptional, 2 reviews
"The house was a really lovely retro house (mid century modern furniture throughout the house) and also had a dart board in a small game room. Everything was well labeled so we knew what was in each of the drawers. Very nice and an easy process! I would go again!"
The price is CA $206
CA $514 total
includes taxes & fees
Jun 4 - Jun 5
Charming 3-bedroom Midcentury modern home, retro vibe and stylish furnishings.
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!
Peaceful Queenstown Home w/ Deck & Grill!
Travelers Rest! Dock, Pool Eastern Shore Private Retreat St. Michaels / Easton
9.6 out of 10, Exceptional, 66 reviews
"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
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
10.0 out of 10, Exceptional, 31 reviews
"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
Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
10.0 out of 10, Exceptional, 8 reviews
"We had a wonderful time! The house was super cute and clean. The views off the water in the morning and the evening were beautiful! All of the blackout shades came in very handy for our baby and little ones who sleep better in darker rooms. The hot tub was magical and taking the kayaks out onto the water was so fun! Only recommendation would be to bring bug spray! Thanks for a wonderful stay. We would love to come back."
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Minutes from Downtown St. Michaels | Pool | Hot Tub
Minutes from Downtown St. Michaels | Pool | Hot Tub
Grasonville Home w/ Private Pool on the Water
10.0 out of 10, Exceptional, 13 reviews
"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 reviews
"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
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub
10.0 out of 10, Exceptional, 1 review
"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
Downtown St. Michaels | Bikes | Kayaks | Private Pier
9.8 out of 10, Exceptional, 20 reviews
"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
Luxury Waterfront Retreat with in ground pool and close to town
10.0 out of 10, Exceptional, 24 reviews
"We stayed here as two families for thanksgiving. The kids (ages 6-15) loved the upstairs. So cozy and the game room was great for family movie night. The kitchen was perfect for all of our cooking. Lots of counter space, drink fridge really helped give extra space in main fridge, kitchen is very well stocked with pots, bakeware, crockpot, blender, and plenty of dinnerware/silverware. The backyard, dock, patio, and awesome view of the sunsets was our afternoon/evening entertainment. We went into...
Luxury Waterfront Retreat with in ground pool and close to town
Minutes from Downtown St. Michaels | Pool | Pool House | Kayaks | Private Dock
Minutes from Downtown St. Michaels | Pool | Pool House | Kayaks | 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

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, 105 reviews
"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!
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, 4 reviews
"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!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, 108 reviews
"VRBO link hasn’t enabled me to communicate with property manger/owner as I’m unable to access account via the VRBO link. I’ve re-registered multiple times now."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
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.

Trappe Vacation Homes information

Number of reviews
212
Accommodation
184 Vacation Homes
Lowest Price
CA $206
Highest Price
CA $206

Recent Reviews in Trappe
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