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Top Holiday Rentals in Trappe

Our top choices for Trappe holiday rentals

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (255)
"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "
Family and Pet-Friendly, Waterfront with Pier

Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops

10.0 out of 10, Exceptional, (22)
"Stayed for the weekend- parked the car and could walk to everything- perfect. Host was super responsive and the place was super clean!"
Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (122)
"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (184)
"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. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Harbor View Suite

10.0 out of 10, Exceptional, (27)
"The room and location were perfect. Very clean and comfortable space to stay and right in the heart of town. "
Harbor View Suite

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (51)
"This exceptional property was our best homestay experience yet across several states and countries. The unit has so many customized features that make it stand out, from the fire pit (fire already built) and sauna (water bucket already filled) to the kitchen and bedrooms, where no detail has been missed. The owners were extremely proactive and responsive throughout our stay, and we look forward to booking again soon. "
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

9.6 out of 10, Exceptional, (142)
"A lovely cottage to stay in. Lots of old world charm and location is unbeatable when want to stay in St. Michaels"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (7)
"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (12)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is £293
includes taxes & fees
3 Sept - 4 Sept
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

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."
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (10)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

9.6 out of 10, Exceptional, (32)
"This house is awesome - very large and has room for all! It also has some old charm character and features that were really fun, like two "hidden staircases" the kids loved! Bedroom layouts were smartly planned to accommodate large groups and families. The property is truly gorgeous and huge - trails in the woods, lakes, tons of space for yard games and a swing set with two working swings. Parking was abundant, great basketball court and well stocked with the basics! The indoor pool is literally...
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (119)
"We once again enjoyed our stay here. Perfect location to every where you’d want to go in St. Michael’s! Loved sitting out front looking at the water and park and enjoying music from our front yard. Highly recommend this cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

25-50% Off~Private Beach~Hot Tub~Fire Table~

10.0 out of 10, Exceptional, (26)
"Excellent property, great communication with the hosts. Quite and relaxing"
25-50% Off~Private Beach~Hot Tub~Fire Table~

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

9.8 out of 10, Exceptional, (41)
"Good location, clean house, easy check in and check out process."
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Waterfront property with private boat ramp and new dock!

9.4 out of 10, Exceptional, (13)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

10.0 out of 10, Exceptional, (14)
"Gorgeous views and location. "
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

9.8 out of 10, Exceptional, (132)
"Great house, host and location. Stayed with a larger group and plenty of room!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Walk to Everything House

10.0 out of 10, Exceptional, (81)
"Clean and nice place to stay"
Walk to Everything House

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

10.0 out of 10, Exceptional, (89)
"6 women for the 6 bedroom home. The house was great for our weekend. The only complaint was that the weather did not allow for more outdoor activities, though we had plenty of space inside to enjoy ourselves. The house has all the amenities and more. "
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
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

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 £293 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?

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW: This holiday home rental outside Trappe is located on the waterfront, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 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.