A rural landscape with a dirt road leading to a red barn, surrounded by fields and a clear sky.

Trappe Vacation Rentals

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Our top choices for Trappe vacation rentals

1. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is AED 569
AED 895 total
includes taxes & fees
29 Sep - 30 Sep
Sailwinds Loft at Cambridge Creek

2. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (14 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is AED 533
AED 1,226 total
includes taxes & fees
28 Sep - 29 Sep
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

3. 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
9.0 out of 10, Wonderful, (14 reviews)
"Very spacious home. 4 bedrooms and 4 baths. Great basement for watching TV with a large group. Home is about 15 minutes from downtown Cambridge."
United States
Anonymous traveler
The price is AED 1,378
AED 2,415 total
includes taxes & fees
28 Sep - 29 Sep
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

4. More, than just a place to sleep - welcome home!

More, than just a place to sleep - welcome home!
Cambridge
The price is AED 1,091
AED 1,431 total
includes taxes & fees
28 Sep - 29 Sep
More, than just a place to sleep - welcome home!

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

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (25 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
The price is AED 661
AED 1,367 total
includes taxes & fees
27 Oct - 28 Oct
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

6. 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, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is AED 1,192
AED 2,116 total
includes taxes & fees
27 Oct - 28 Oct
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

7. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (66 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is AED 760
AED 884 total
includes taxes & fees
4 Oct - 5 Oct
Waterfront Getaway with Dock

8. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is AED 1,322
AED 2,114 total
includes taxes & fees
6 Oct - 7 Oct
Turnbridge Manor

9. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford
9.6 out of 10, Exceptional, (35 reviews)
"Beautiful piece of property and clean, comfortable accommodations! Would definitely return if plan to be in that area again!!"
United States
Joyce F.
The price is AED 1,306
AED 2,342 total
includes taxes & fees
5 Oct - 6 Oct
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

10. 5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
Stevensville
8.0 out of 10, Very good, (5 reviews)
"We arrived and the air conditioning was broken.The owner did not inform us but installed portable AC’s running vents out of doors that would not close or lock. The old AC unit was installed incorrectly &BR below flooded by 12 am. contacted owner and then was told not to run AC & we would be refunded. Covered mattresses that were being soaked, cleaned up flood, washed all bedding. Owner said trying to find us another rental but there were none & I had service dog. If we moved we would miss...
United States
Suzanne R.
The price is AED 2,645
AED 3,656 total
includes taxes & fees
10 Oct - 11 Oct
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking

11. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is AED 1,001
AED 1,592 total
includes taxes & fees
28 Sep - 29 Sep
Plum Point Cottage #17

12. 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, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is AED 1,010
AED 1,760 total
includes taxes & fees
28 Sep - 29 Sep
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

13. Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is AED 529
AED 1,566 total
includes taxes & fees
27 Oct - 28 Oct
Family Beach House: Spacious Deck, Grill & Views
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

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?

Private 2 Acre Waterfront Family Retreat with Pool & Pier: Visitors like this Trappe vacation home rental. It is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

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.