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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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Trappe vacation rentals

Interior

1. Pet-Friendly Pond Cottage • Nature Escape Near Beaches

Pet-Friendly Pond Cottage • Nature Escape Near Beaches
Seaford
The price is AED 544
AED 654 total
includes taxes & fees
9 Sep - 10 Sep
Pet-Friendly Pond Cottage • Nature Escape Near Beaches
Marina

2. Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8

Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our weekend getaway at the beautiful gated community. Great water views and a walkable community. The townhouse met all our needs. Fully stocked with essential items. The added bonus is a the workout room with top of the line equipment. A nice touch! Two great decks overlooking the marina. The owners are very responsive."
United States
Melissa
The price is AED 1,194
AED 1,602 total
includes taxes & fees
12 Aug - 13 Aug
Brand New Waterfront Home • Pool • Walk Downtown & Events • Sleeps 8
Private kitchen

3. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (38 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is AED 569
AED 934 total
includes taxes & fees
13 Aug - 14 Aug
Sailwinds Loft at Cambridge Creek
Smart TV

4. 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)
"Clean, cozy, and lovely - a winter cabin stay to remember. Kids already wanted to go back 5 days later. 10 out of 10 stars! "
United States
Mr.
The price is AED 1,371
AED 2,524 total
includes taxes & fees
12 Aug - 13 Aug
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Marina

5. Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Downtown Cambridge
10.0 out of 10, Exceptional, (12 reviews)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is AED 1,102
AED 2,001 total
includes taxes & fees
26 Aug - 27 Aug
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Marina

6. 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, (13 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is AED 1,028
AED 1,916 total
includes taxes & fees
26 Aug - 27 Aug
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Marina

7. 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, (24 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 1,028
AED 1,916 total
includes taxes & fees
8 Sep - 9 Sep
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina

8. Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Downtown Cambridge
8.4 out of 10, Very Good, (9 reviews)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is AED 735
AED 1,448 total
includes taxes & fees
26 Aug - 27 Aug
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
1 bedroom, iron/ironing board, WiFi, bed sheets

9. Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing

Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Downtown Cambridge
The price is AED 544
AED 993 total
includes taxes & fees
17 Aug - 18 Aug
Pint-Sized on Poplar - Contemporary Cambridge Apartment Across from RAR Brewing
Coffee/tea maker, fridge, microwave, oven

10. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (64 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is AED 845
AED 989 total
includes taxes & fees
17 Aug - 18 Aug
Waterfront Getaway with Dock
Smart TV

11. 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, (15 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is AED 1,498
AED 2,589 total
includes taxes & fees
12 Aug - 13 Aug
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Property grounds

12. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (15 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is AED 1,322
AED 2,270 total
includes taxes & fees
12 Aug - 13 Aug
Turnbridge Manor
Outdoor dining

13. Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (45 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
The price is AED 1,414
AED 1,784 total
includes taxes & fees
8 Sep - 9 Sep
Sunset Breezes - quiet waterfront retreat
Dining

14. 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, (15 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 918
AED 1,557 total
includes taxes & fees
12 Aug - 13 Aug
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Outdoor dining

15. Waterfront Escape with Pool Nature Lover Paradise

Waterfront Escape with Pool Nature Lover Paradise
Stevensville
10.0 out of 10, Exceptional, (3 reviews)
"N"
United States
Maria S.
The price is AED 2,370
AED 4,428 total
includes taxes & fees
23 Aug - 24 Aug
Waterfront Escape with Pool Nature Lover Paradise
Pool

16. 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 683
AED 1,877 total
includes taxes & fees
2 Sep - 3 Sep
Family Beach House: Spacious Deck, Grill & Views
Exterior

17. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is AED 1,001
AED 1,693 total
includes taxes & fees
12 Aug - 13 Aug
Plum Point Cottage #17
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

St Michaels Inn

St Michaels Inn

10/10 Excellent
"We enjoyed our stay. Rooms were clean and the staff were very friendly. Looking forward to our next visit to St Michael’s. We would definitely stay here again."
Lori 2-night trip
Posted 8 hours ago
St Michaels Inn

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?

Relax on Kent Island in a 4 Bedroom Home w/Waterview!: Visitors like this Trappe vacation home rental. It offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.