Search Vacation Homes in Trappe

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In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Trappe vacation homes

Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.6 out of 10, Exceptional, (20)
"In town for a family wedding. This worked out perfectly. Would stay there again "
United States
Barbara V.
$322 nightly
The price is $341
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Interior
Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!

Beautiful Waterfront Retreat in Cambridge!
Cambridge
10.0 out of 10, Exceptional, (50)
"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"
United States
Karen L.
$352 nightly
The price is $373
Jan 4 - Jan 5, 2026
Total with taxes and fees
Beautiful Waterfront Retreat in Cambridge!
Property grounds
Turnbridge Manor

Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (12)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
$575 nightly
The price is $610
Dec 29 - Dec 30
Total with taxes and fees
Turnbridge Manor
Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock

Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (51)
"Great place, will stay again"
United States
Matt S.
$263 nightly
The price is $279
Dec 25 - Dec 26
Total with taxes and fees
Waterfront Getaway with Dock
Pool
Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeake Beach
9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
$411 nightly
The price is $432
Jan 21 - Jan 22, 2026
Total with taxes and fees
Family Beach House: Spacious Deck, Grill & Views
Exterior
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
$389 nightly
The price is $412
Dec 25 - Dec 26
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Smart TV
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (14)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
$498 nightly
The price is $528
Jan 2 - Jan 3, 2026
Total with taxes and fees
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Property grounds
Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (41)
"Good time with my friends "
United Kingdom
Oleg L.
$298 nightly
The price is $329
Dec 30 - Dec 31
Total with taxes and fees
Sunset Breezes - quiet waterfront retreat
Interior
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
8.8 out of 10, Excellent, (9)
"This home was everything we needed and more! It was spacious, clean and a beautiful location! There was a leak in the ceiling and the owners were very responsive and fixed it right away. Definitely recommend this stay."
United States
Priscilla A.
$593 nightly
The price is $628
Jan 6 - Jan 7, 2026
Total with taxes and fees
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF 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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Top Trappe Hotel Reviews

The Wildset

The Wildset

10/10 Excellent
"Well decorated inn w spacious and clean rooms, walking distance to shops, great restaurant with bar & breakfast included. Would absolutely come back. "
Jenn 1-night trip
Posted 8 days ago
The Wildset

Find out more about Trappe

Trappe Vacation Homes information

Number of reviews
215
Accommodation
225 Vacation Homes
Lowest Price
$279
Highest Price
$628

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