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Browse Select Trappe Vacation Homes

Our top choices for Trappe vacation homes

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (12)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is CA $221
CA $517 total
includes taxes & fees
Aug 27 - Aug 28
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (44)
"Our kids enjoyed the games in the crab house. It was great being able to use the kayaks and life vests."
The price is CA $306
CA $622 total
includes taxes & fees
Sep 7 - Sep 8
Beautiful Waterfront Retreat in Cambridge!

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

9.4 out of 10, Exceptional, (28)
"I cannot say enough about this property. Home was so spacious, views were wonderful, kitchen was very well stocked and just minutes to town. Highly recommend renting this home."
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

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

10.0 out of 10, Exceptional, (26)
"Excellent property, great communication with the hosts. Quite and relaxing"
25-50% Off~Private Beach~Hot Tub~Fire Table~

Amazing views waterfront 3-bedroom home in Madison

9.6 out of 10, Exceptional, (5)
Amazing views waterfront 3-bedroom home in Madison

Peaceful Queenstown Home w/ Deck & Grill!

9.6 out of 10, Exceptional, (9)
"Enjoyed this lovely and comfortable home tucked away in a private location close to amenities. "
Peaceful Queenstown Home w/ Deck & Grill!

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

9.8 out of 10, Exceptional, (132)
"Great house, host and location. Stayed with a larger group and plenty of room!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Walk to Everything House

10.0 out of 10, Exceptional, (81)
"Clean and nice place to stay"
Walk to Everything House

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

9.8 out of 10, Exceptional, (48)
"wonderful home and great views. Clean, quiet, plenty of amenities"
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

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

9.8 out of 10, Exceptional, (41)
"Good location, clean house, easy check in and check out process."
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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

8.6 out of 10, Excellent, (8)
"Spacious, orderly interior, lovely setting, great amenities: kayaks, fire pit, creek feeds into Chop tank, close to Saint Michaels and Secretary.Big bedrooms with new comfy beds, plenty of bathrooms and showers.Just a lovely place and excellent communication from host."
The price is CA $478
CA $912 total
includes taxes & fees
Aug 26 - Aug 27
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Heated pool, sandy beach, pier, and playground set punch point apart!

10.0 out of 10, Exceptional, (10)
"Beautifully decorated, peaceful, well appointed home for our girls bday celebration. Highly recommend."
Heated pool, sandy beach, pier, and playground set punch point apart!

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

2.0 star property
8.4 out of 10, Very good, (7)
"House was spacious plenty of room, great amenities, and very clean! "
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (21)
"Loved the location, the property, and amenities. Would definitely stay again!"
Waterfront Sunset Bayview: sleeps 6

Modern Country Home with Pool and Game Room

9.4 out of 10, Exceptional, (6)
"Nice place. Well accommodated."
Modern Country Home with Pool and Game Room

Escape with family or friends to this peaceful, 4-bedroom retreat on the water

2.0 star property
10.0 out of 10, Exceptional, (7)
"House is clean, renovated, and comfortable. View was gorgeous. Hosts were helpful and timely in communications. Enthusiastically recommend. "
Escape with family or friends to this peaceful, 4-bedroom retreat on the water

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

9.4 out of 10, Exceptional, (8)
"Thank you for a beautiful stay! Well appointed kitchen, comfortable beds and a pristine lot. "
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

10.0 out of 10, Exceptional, (9)
"This is such a special property. The house, the amenities and then the surprising foodie scene in Easton and St. Michael’s is within minutes. This is our second summer at this property and we are already starting to plan our third!"
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

10.0 out of 10, Exceptional, (9)
"My husband and I spent Christmas on Tilghman Island in this unique house right on the water. It was perfect for us to rest, relax and cook Christmas dinner. We enjoyed it so much we want to visit again when the boats are out. The yard was perfect for our dog to get some exercise. I can see this as a perfect place for family and friends in the summer."
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien

10.0 out of 10, Exceptional, (4)
"Very relaxing house to stay in. Plenty of room and well stocked kitchen . Close to St. Michaels and Cambridge. We were there for the Eagleman triathlon and we really enjoyed the seclusion. "
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien
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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