Holiday Rentals in Trappe

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Our top choices for Trappe holiday rentals

10.0 out of 10, Exceptional, (7)
The price is €222
includes taxes & fees
5 Jan - 6 Jan 2026
Station House East: Upscale Loft in the Historic District Cambridge, MD
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 €299
includes taxes & fees
5 Jan - 6 Jan 2026
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
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 €303
includes taxes & fees
5 Jan - 6 Jan 2026
Conductor's Rest: Beautiful 2 Bedroom Loft in Historic Cambridge, Maryland
10.0 out of 10, Exceptional, (26)
"Quiet, quaint....perfect"
United States
Catherine M.
Adorable two-bedroom retreat close to Easton, Denton, Centreville
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 €250
includes taxes & fees
5 Jan - 6 Jan 2026
Station House West: Upscale Condo in Historic Downtown Cambridge, Maryland
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 €299
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

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 €223
includes taxes & fees
26 Dec - 27 Dec
Sailwinds Loft at Cambridge Creek
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 €327
includes taxes & fees
4 Jan - 5 Jan 2026
Beautiful Waterfront Retreat in Cambridge!
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.
Beach Front, Bay View, Fishing, chesapeake,Family Getaway

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 €533
includes taxes & fees
29 Dec - 30 Dec
Turnbridge Manor
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
The price is €776
includes taxes & fees
24 Dec - 25 Dec
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
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 €501
includes taxes & fees
5 Jan - 6 Jan 2026
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

Holiday Home in Woolford

Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (51)
"Great place, will stay again"
United States
Matt S.
Waterfront Getaway with Dock

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.
Sunset Breezes - quiet waterfront retreat
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 €563
includes taxes & fees
23 Dec - 24 Dec
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
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.
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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

Everything you need to know about Trappe holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Trappe holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Trappe holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Trappe holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Trappe. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Trappe holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Trappe holiday rentals we have selected for you start as low as €327 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Trappe rentals

At Expedia, we put the best Trappe holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Trappe rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Trappe holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Trappe. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28: This holiday home rental outside of Trappe is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.