Trappe Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Trappe holiday rentals

Marina
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Condo in Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
2.0 star property
9.8 out of 10, Exceptional, (11)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
United States
Lauren V.
The price is HK$1,089
HK$2,696 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Private kitchen
Sailwinds Loft at Cambridge Creek

Apartment in Cambridge

Sailwinds Loft at Cambridge Creek
10.0 out of 10, Exceptional, (24)
"What a great place to relax after exploring and enjoying the area. Definitely will visit again "
United States
Chris S.
The price is HK$1,205
HK$1,978 total
includes taxes & fees
29 Dec - 30 Dec
Sailwinds Loft at Cambridge Creek
Marina
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland

Condo in Downtown Cambridge

Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
2.5 star property
10.0 out of 10, Exceptional, (10)
"Just a beautiful place. I would stay here again. Everything was walking distance. "
United States
Sylvie G.
The price is HK$1,167
HK$2,795 total
includes taxes & fees
5 Jan - 6 Jan 2026
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Holiday Home in Cambridge

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
9.6 out of 10, Exceptional, (20)
"In town for a family wedding. This worked out perfectly. Would stay there again "
United States
Barbara V.
The price is HK$1,128
HK$2,745 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina
Station House East: Upscale Loft in the Historic District Cambridge, MD

Condo in Downtown Cambridge

Station House East: Upscale Loft in the Historic District Cambridge, MD
10.0 out of 10, Exceptional, (7)
The price is HK$505
HK$2,028 total
includes taxes & fees
11 Jan - 12 Jan 2026
Station House East: Upscale Loft in the Historic District Cambridge, MD
Interior
Beautiful Waterfront Retreat in Cambridge!

Holiday Home in Cambridge

Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (50)
"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"
United States
Karen L.
The price is HK$1,225
HK$2,897 total
includes taxes & fees
8 Jan - 9 Jan 2026
Beautiful Waterfront Retreat in Cambridge!
Marina
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland

Condo in Downtown Cambridge

Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
8.4 out of 10, Very good, (6)
"Perfectly located in town and well appointed, comfortable quarters. We would stay again."
United States
Richard D.
The price is HK$933
HK$2,300 total
includes taxes & fees
14 Jan - 15 Jan 2026
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
Property grounds
Turnbridge Manor

Holiday Home in Denton

Turnbridge Manor
9.8 out of 10, Exceptional, (12)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is HK$2,799
HK$4,739 total
includes taxes & fees
29 Dec - 30 Dec
Turnbridge Manor
Pool
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Holiday Home in Chesapeake Beach

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
9.0 out of 10, Wonderful, (6)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is HK$1,509
HK$3,675 total
includes taxes & fees
25 Jan - 26 Jan 2026
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock

Holiday Home in Woolford

Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (51)
"Great place, will stay again"
United States
Matt S.
The price is HK$1,788
HK$2,085 total
includes taxes & fees
20 Jan - 21 Jan 2026
Waterfront Getaway with Dock
Smart TV
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Holiday Home in Cambridge

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
10.0 out of 10, Exceptional, (14)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is HK$2,040
HK$4,108 total
includes taxes & fees
2 Jan - 3 Jan 2026
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Exterior
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Holiday Home in Grasonville

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is HK$1,944
HK$3,198 total
includes taxes & fees
26 Dec - 27 Dec
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Smart TV, fireplace, books, printers
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Cottage in Stevensville

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
The price is HK$3,103
HK$6,882 total
includes taxes & fees
28 Dec - 29 Dec
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Property grounds
Sunset Breezes - quiet waterfront retreat

Holiday Home in Dorchester County

Sunset Breezes - quiet waterfront retreat
10.0 out of 10, Exceptional, (41)
"Good time with my friends "
United Kingdom
Oleg L.
The price is HK$1,998
HK$2,490 total
includes taxes & fees
30 Dec - 31 Dec
Sunset Breezes - quiet waterfront retreat
Interior
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

Holiday Home in Cambridge

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
8.8 out of 10, Excellent, (9)
"This home was everything we needed and more! It was spacious, clean and a beautiful location! There was a leak in the ceiling and the owners were very responsive and fixed it right away. Definitely recommend this stay."
United States
Priscilla A.
The price is HK$2,479
HK$4,878 total
includes taxes & fees
2 Jan - 3 Jan 2026
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Trappe Hotel Reviews

Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Fantastic - loved our stay!"
Emily 1-night trip
Posted 1 day ago
Inn at Perry Cabin

Find out more about Trappe

Search for holiday rentals in Trappe on Expedia! You can easily find your home rentals, villas, holiday apartments in Trappe using one of the methods below:

  • View our selection of featured holiday rentals in Trappe
  • Use the map to find apartments and other holiday homes in the Trappe neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Trappe while they last

Look no further and take a look at our great range of rental properties in Trappe!

Frequently asked questions

Can I find a holiday rental in Trappe?

Yes, there are holiday rentals close to the most popular sights in Trappe, or you can select a more secluded option if you're looking for a relaxing stay. Trappe is known for its waterfront and parks.

What are some of the best holiday rentals that Trappe has to offer?

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks: This holiday home rental outside of Trappe is located in a rural location, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Trappe?

With 4 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find Bill Burton Fishing Pier State Park and Choptank River Lighthouse.

What’s a holiday rental in Trappe like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Trappe. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for family trips.