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

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Trappe vacation homes

A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

1. 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 CA $233
CA $534 total
includes taxes & fees
Oct 27 - Oct 28
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
A bedroom with a bed, a dresser, a mirror, and a window with curtains.

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

More, than just a place to sleep - welcome home!
Cambridge
The price is CA $420
CA $563 total
includes taxes & fees
Oct 2 - Oct 3
More, than just a place to sleep - welcome home!
A wooden interior with a dining area, sofas, and a table.

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, (15 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 $486
CA $930 total
includes taxes & fees
Sep 30 - Oct 1
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
A kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a sink.

4. Waterfront Getaway with Dock

Waterfront Getaway with Dock
Woolford
10.0 out of 10, Exceptional, (67 reviews)
"It was perfect for our overnight on way to NY!"
United States
Meagan G.
The price is CA $293
CA $352 total
includes taxes & fees
Oct 4 - Oct 5
Waterfront Getaway with Dock
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

5. 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 CA $434
CA $829 total
includes taxes & fees
Sep 30 - Oct 1
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A spacious living room with a large TV, blue sofa, and a ceiling fan.

6. 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 CA $503
CA $938 total
includes taxes & fees
Oct 6 - Oct 7
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

7. 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.
Sunset Breezes - quiet waterfront retreat
A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

8. 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 CA $425
CA $769 total
includes taxes & fees
Sep 30 - Oct 1
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

9. 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 CA $509
CA $874 total
includes taxes & fees
Sep 30 - Oct 1
Turnbridge Manor
Pool

10. 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 CA $204
CA $643 total
includes taxes & fees
Oct 27 - Oct 28
Family Beach House: Spacious Deck, Grill & Views
A single-story house with a gabled roof, a front porch, and a small front yard with a flag.

11. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is CA $385
CA $653 total
includes taxes & fees
Oct 1 - Oct 2
Plum Point Cottage #17
A two-story house with a red roof, a brick chimney, and a small porch.

12. 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 CA $1,018
CA $1,490 total
includes taxes & fees
Oct 4 - Oct 5
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

The Tilghman Island Inn

The Tilghman Island Inn

10/10 Excellent
"This hotel is absolutely amazing. The bed was comfortable, the temperature. TBH"
Essence 2-night trip
Posted 17 hours ago
The Tilghman Island Inn

Find out more about Trappe

Trappe Vacation Homes information

Number of reviews
233
Accommodation
245 Vacation Homes
Lowest Price
CA $352
Highest Price
CA $1,490

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