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, 39, (39 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is CA $215
CA $353 total
includes taxes & fees
Sep 15 - Sep 16
Sailwinds Loft at Cambridge Creek

2. 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, 25, (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 CA $243
CA $547 total
includes taxes & fees
Sep 30 - Oct 1
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

3. 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, 13, (13 reviews)
"Great stay! Gorgeous apartment!"
United States
Kristen S.
The price is CA $236
CA $538 total
includes taxes & fees
Sep 28 - Sep 29
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

4. Waterfront • Heated Decks • Workspace • EV Charging • Home Gym • Downtown

Waterfront • Heated Decks • Workspace • EV Charging • Home Gym • Downtown
Cambridge
10.0 out of 10, 2, (2 reviews)
"We only stayed one night but wouldn't hesitate to come back and stay for a few days. Beautiful home overlooking the docks."
United States
mike
The price is CA $531
CA $1,047 total
includes taxes & fees
Sep 20 - Sep 21
Waterfront • Heated Decks • Workspace • EV Charging • Home Gym • Downtown

5. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, 66, (66 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
Waterfront Getaway with Dock

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

Pet-Friendly Pond Cottage • Nature Escape Near Beaches
Seaford
The price is CA $158
CA $196 total
includes taxes & fees
Oct 12 - Oct 13
Pet-Friendly Pond Cottage • Nature Escape Near Beaches

7. 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, 14, (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 traveller
The price is CA $466
CA $898 total
includes taxes & fees
Sep 15 - Sep 16
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

8. 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, 35, (35 reviews)
"Anne is a great host, always responded promptly regardless of time.Property is huge! Lots of patio space, and included kayaks for us to use. Next time in the area will definitely stay there"
United States
Ramon A.
The price is CA $599
CA $1,062 total
includes taxes & fees
Sep 15 - Sep 16
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

9. 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, 16, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is CA $453
CA $849 total
includes taxes & fees
Sep 16 - Sep 17
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

10. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, 18, (18 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is CA $499
CA $847 total
includes taxes & fees
Sep 15 - Sep 16
Turnbridge Manor

11. 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, 16, (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 CA $381
CA $712 total
includes taxes & fees
Sep 15 - Sep 16
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

12. Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, 45, (45 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
The price is CA $535
CA $675 total
includes taxes & fees
Sep 27 - Sep 28
Sunset Breezes - quiet waterfront retreat

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

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, 7, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is CA $200
CA $635 total
includes taxes & fees
Sep 15 - Sep 16
Family Beach House: Spacious Deck, Grill & Views

14. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $378
CA $641 total
includes taxes & fees
Sep 15 - Sep 16
Plum Point Cottage #17

15. 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
7.6 out of 10, 4, (4 reviews)
"The place was very clean and Host was ok the shopping was six miles away, not in walking distance, we had no pets on this trip."
United States
Anonymous traveller
The price is CA $999
CA $1,462 total
includes taxes & fees
Sep 16 - Sep 17
5-bedroom waterfront home on 1.5 acres in Stevensville with tons of parking
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

Find out more about Trappe

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Trappe. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.