Trappe Holiday Rentals

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Holiday Rentals in Trappe

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
10.0 out of 10, Exceptional, (14)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
United States
Dara M.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Family and Pet-Friendly, Waterfront with Pier
10.0 out of 10, Exceptional, (262)
"Our stay was great and Rob and Clarissa were very welcoming!"
United States
Allison L.
Family and Pet-Friendly, Waterfront with Pier
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
9.6 out of 10, Exceptional, (19)
"Great well-furnished townhouse in a great location and a super responsive host. What’s not to like?!?!"
United States
Lynn
The price is AU$598
includes taxes & fees
18 Nov - 19 Nov
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (122)
"The house and location was perfect for a girls weekend with my mom and 2 daughters! The 1/2 bathrooms in each bedroom were nice to have upstairs!"
United States
Kimberly L.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
10.0 out of 10, Exceptional, (78)
"Good stay overall"
United States
Bill C.
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
9.8 out of 10, Exceptional, (7)
"The property was perfect for our family get together. We had a baby, toddler, preschooler, elementary and teens, moms, dads and grandparents. There was a place for everyone. Having a pack n’ play available would have been nice, but we procured one elsewhere. The property was large and felt very private, but Cambridge was just a quick drive."
United States
Jacqueline M.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, (74)
"We had a wonderful stay including boating, kayaking, swimming, fishing, campfires and crabs! The house was perfect for our group and the owner was very accommodating."
United States
Susan G.
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (44)
"This cottage is adorable. Great amenities and great location. We thoroughly enjoyed our time in St Michael’s."
United States
Audra B.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (145)
"Perfect place to stay for a cousins reunion, Central location to all the shops and restaurants."
United States
Amh S.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
10.0 out of 10, Exceptional, (14)
"Beautiful location, great views, beautiful sun rises, view of working watermen Dogwood Harbour. Owner met us at the property with a bottle of wine — very friendly. Tilghman Island is a quaint and beautiful gem."
United States
Frank P.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (6)
"This VRBO was very clean. Since it is a fairly new addition to VRBO, we thought it could use a little more info, like a portfolio with the combination to the bike locks, where to go to eat and visit, etc. Also, the only coffeemaker was a Keurig and we didn’t bring any K-cups. The 4 of us had a nice 50th Anniversary long weekend."
United States
Sharon M.
The price is AU$1,407
includes taxes & fees
5 Nov - 6 Nov
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (191)
"This house has the perfect location to explore the town. We stayed in this house for the St. Michael’s Running Festival and it couldn’t have been better. The location was so close to the start/finish lines and there were so many restaurants within a few minutes walk. "
United States
Jen R.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (124)
"Beautiful house Great location. We really enjoyed our first visit to St. Michaels!"
United States
JIM S.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
9.4 out of 10, Exceptional, (20)
"The house was very nice, the host was very responsive! The outside was nice, only down side lots of mosquitos but that’s expected. "
United States
Elizabeth M.
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Modern Flat in the Heart of St. Michaels – Walk Everywhere
10.0 out of 10, Exceptional, (51)
"Beautiful, clean and well appointed in the perfect spot in downtown Saint Michael’s. Highly recommended!!"
United States
Jeffrey G.
Modern Flat in the Heart of St. Michaels – Walk Everywhere
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
10.0 out of 10, Exceptional, (18)
"Gorgeous views and location. "
United States
Ryan D.
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
10.0 out of 10, Exceptional, (137)
"Great location and property. And epic crabbing to top it off!"
United States
June P.
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
10.0 out of 10, Exceptional, (37)
"This is a beautiful property, well appointed, but not too formal for families wanting to be in the pool or on the water all day. We were a party of 12 including six grandchildren. There was plenty to do for the adults and the grandchildren and plenty of space in the home to not feel like you were on top of each other. The sunsets were spectacular. Marissa is an extremely responsive host, and all our questions were answered in a timely fashion. Saint Michaels is very close by and an absolutely...
United States
helen w.
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
9.8 out of 10, Exceptional, (133)
"Beautiful property with gorgeous view. The owner was helpful and accommodating. Everything was clean and the amenities were superb. An evening of kayaking on the water was amazing. Great location for the half Ironman as well! "
United States
Lynn R.
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Heated pool, sandy beach, pier, and playground set punch point apart!
10.0 out of 10, Exceptional, (11)
"Beautifully decorated, peaceful, well appointed home for our girls bday celebration. Highly recommend."
United States
Jackie C.
Heated pool, sandy beach, pier, and playground set punch point apart!
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, 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 favourite 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 depend 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 AU$598 per night. Entering your travel dates in the search wizard might find you 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?

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock: This holiday home rental outside of Trappe is located on a river, and has an outdoor pool, a patio 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. Kick off your shoes and enjoy yourself with a garden and an arcade/games room.

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.