Trappe Vacation Rentals

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Check prices for these dates

Tonight
Jun 22 - Jun 23
Tomorrow
Jun 23 - Jun 24
Next weekend
Jun 27 - Jun 29
In two weeks
Jul 4 - Jul 6

Vacation Rentals in Trappe

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Fridge, microwave, oven, stovetop

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

10.0 out of 10, Exceptional, (4)
"Thank you for a beautiful stay! Well appointed kitchen, comfortable beds and a pristine lot. "
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
View from property

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (45)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
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)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (248)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier
Dollhouse in Central Historic St Michaels
Exterior

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (49)
"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."
Dollhouse in Central Historic St Michaels
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)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is ￥35,062
￥67,053 total
includes taxes & fees
Jun 24 - Jun 25
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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, (5)
"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
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.
Upscale Condo in Historic Downtown Cambridge, Maryland
1 bedroom, iron/ironing board, free WiFi, bed sheets

Upscale Condo in Historic Downtown Cambridge, Maryland

9.4 out of 10, Exceptional, (3)
"The place was very clean and in the most perfect spot in downtown Cambridge. We had a wedding walking distance from this place. Jen is a very responsive and accommodating host!"
The price is ￥30,679
￥58,845 total
includes taxes & fees
Jul 1 - Jul 2
Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (40)
"Very clean, great location"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Outdoor pool

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

10.0 out of 10, Exceptional, (130)
"Great location and property. And epic crabbing to top it off!"
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
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, (119)
"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
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Interior

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

9.8 out of 10, Exceptional, (10)
"This house is huge and has lots of different indoor and outdoor gathering spaces so the kids and adults in our group of three families didn’t have to be on top of each other in one living space the whole time. Big firepit area and huge lawn were great, and we enjoyed the kayaks and canoe. There’s a place to buy fresh crabs, oysters, and shrimp very close by, and the house has everything you need for a crab night. The owner was incredibly responsive and kind."
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Waterfront Getaway with Dock
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (42)
"We appreciated the cleanliness of the home and the location was beautiful and convenient to the state/national park, town and Harriet Tubman museum."
The price is ￥33,601
￥40,572 total
includes taxes & fees
Jul 9 - Jul 10
Waterfront Getaway with Dock
Beautiful Waterfront Retreat in Cambridge!
Fridge, microwave, oven, stovetop

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (37)
"The house was so cute and the fact that we were able to do early check in was amazing!"
The price is ￥42,731
￥76,731 total
includes taxes & fees
Jun 29 - Jun 30
Beautiful Waterfront Retreat in Cambridge!
Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.
Miscellaneous

Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.

2.0 star property
9.6 out of 10, Exceptional, (4)
"The place is tucked away and totally private, beautiful view, comfortable and clean. The owners were very accommodating to one issue that we had with the house resolved quickly. House is equipped with a ton of amenities and a 6seater limo style golf cart to carry everyone and their things to the fishing pier. We wish we had stayed longer. "
Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Sun loungers, beach towels

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

10.0 out of 10, Exceptional, (33)
"Great stay"
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Waterfront Property, kayaks, private dock, near town
Sun loungers, beach towels

Waterfront Property, kayaks, private dock, near town

9.8 out of 10, Exceptional, (151)
"Very nice place! Everything was perfect! Lisa is a great host! Our plane was cancelled so she let us extend our stay free of charge! We will be back!! Thanks Lisa!"
Waterfront Property, kayaks, private dock, near town
25-50% Off~Private Beach~Hot Tub~Fire Table~
On the beach, beach towels

25-50% Off~Private Beach~Hot Tub~Fire Table~

10.0 out of 10, Exceptional, (26)
"It was the perfect romantic getaway! "
25-50% Off~Private Beach~Hot Tub~Fire Table~
Charming Summer Cottage – Relax and Unwind Here!
Miscellaneous

Charming Summer Cottage – Relax and Unwind Here!

10.0 out of 10, Exceptional, (8)
"A delightful, quiet and peaceful spot for a family getaway."
Charming Summer Cottage – Relax and Unwind Here!
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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Frequently asked questions

Can I find a vacation rental in Trappe?

Yes, we give you a choice of vacation rentals near popular attractions in Trappe, or you can choose a more remote option if you're looking for a relaxing stay. Trappe is known for its waterfront and parks.

What's the top vacation rental in Trappe?

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina: Visitors like this Trappe vacation home rental. It is located in the city center and has a garden, a selection of games, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Trappe?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Trappe stay.

What’s there to see and do in Trappe?

While exploring the area, visit family-friendly sights like Chesapeake Bay Maritime Museum, or get outside and enjoy nature at Gerry Boyle Park at Great Marsh. In the larger area, you’ll find Bill Burton Fishing Pier State Park and Choptank River Lighthouse.

What’s a vacation rental in Trappe like?

Vacation rentals are privately owned properties you can book for a couple of days or more in Trappe. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for small groups.