Trappe Holiday Rentals from €271: Search Short-Term Rentals

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

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock! : This holiday home rental outside of Trappe is located on a lake, and has a fireplace, a balcony 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. You can relax into your holiday with a selection of games and 1 hot tub.

Check Trappe holiday rental availability

Holiday Rentals in Trappe

"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"

"We thoroughly enjoyed the convenience of walking to shops, restaurants, and waterfront! Residence was charming and clean! Only minor issue was we couldn’t locate the iron- just the ironing board! We still had fun but we’re just a bit wrinkled!😁"

"We had the most wonderful time at this charming house on Tillman Island! While the pics are great, it is even better in person. The house is perfectly nestled on the waterway, offering stunning views. The backyard pool was a true highlight, and we spent countless hours splashing around, the pool in the sun."

"We loved this house, it was perfect for exploring town and as a base for things further afield. Comfortable, thoughtfully and well stocked with lots of charm."

" October 11-14, 2024, we rented the “Willoughby” for a family reunion. Let me start out by saying this home is amazing. It looks exactly as pictured based on the website photos. It was even better than I expected. If you are considering this property, I highly recommend booking it! Believe me when I say the Willoughby is a rare gem. The location of the home is perfect and extremely private. The grounds are pristine and the view of the water is breathtaking. The home sits on the Hudson...

"Had a great visit. House was perfect and the area is absolutely gorgeous"

"Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway...

"The house was amazing! From the moment the front door opened it was a visual feast. The views are incredible, it's quiet, private and very relaxing. There were personal elements reflecting the current and original owners which we found very interesting and the attention to detail throughout was superb! Everything was incredibly well stocked with a multitude of extras. "

"We went to St. Michael’s for a wedding. The cottage was great. Very charming. The location was perfect. We could walk everywhere. We had great communication with the host. He was very accommodating. We will stay there again. "

"Perfect large space on a quiet and pretty area. Really great space. "

"This house is huge and has lots of different indoor and outdoor gathering spaces so the kids and adults in our group of three families didn’t have to be on top of each other in one living space the whole time. Big firepit area and huge lawn were great, and we enjoyed the kayaks and canoe. There’s a place to buy fresh crabs, oysters, and shrimp very close by, and the house has everything you need for a crab night. The owner was incredibly responsive and kind."

"Every morning I made coffee, lit the fire pit on the dock and spent at least from 30 minutes before sunrise to 30 after. Used Merlin to identify bird calls. Heard and saw bald eagles, a belted kingfisher and an eastern bluebird. Watched a great blue heron fishing. Heard many many different birds. Truly an awesome location to slow down and enjoy the moment "

includes taxes & fees

15 Dec - 16 Dec

"I highly recommend staying here for a cozy couples weekend. It was absolutely beautiful and quiet. The host was so nice and made us feel welcome. I can’t wait to stay here again."

includes taxes & fees

11 Dec - 12 Dec

"This is a hidden jewel. We had so much fun fishing and crabbing. The home was everything you could ever ask for. We will definitely be back next year for a longer stay. If you are looking for some peace and quiet, this is the place to be. Thank you to the owners for making this a great place. "

"We enjoyed our time at the house very much. We went out to dinner only once and the rest of the time we ate in. We grilled two nights and made a roast one night. The views and the pool were more than you could imagine."

"Our stay was amazing. The house is beautiful. The views and peaceful location were completely used. We had many fun game nights and dinners around the table, the kitchen easily provided many happy meals. The gas grill, the fire pit were easy to use. The kayaks were a lot of fun. Sitting on the dock enjoying the peaceful quiet mornings was rejuvenating. The pool chairs and umbrellas were really nice. A ping pong table in the garage was a ton of fun too. The extra fridge/freezer was handy and the...

"Great rental experience. Barb was fantastic at communicating. The house was perfect for our group, including some adults and some young children. Yard and dock were a blast for playing and fishing. "

"This was a quick getaway for my husband, me, and our 2-year-old grandson. The location of this property is perfect! We could walk over to the waterfront and watch the geese or walk into town for shopping and food. We lost power (a fluke) during our stay, and the owner was extremely responsive and easy to contact. We walked to dinner, and it was back on when we returned. Highly recommend!"

"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."

includes taxes & fees

1 Dec - 2 Dec

"This was the most peaceful and perfect property. I felt like I was on vacation and able to relax! We would definitely return if we are in the area again."

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Other types of properties in Trappe you may be interested in

Indoor pool, 2 outdoor pools, pool umbrellas, pool loungers

"Anniversary. Great time. Beautiful property "

includes taxes & fees

18 Dec - 19 Dec

Breakfast, lunch, dinner served; sea views

"Everything about this property was exceptional! Definitely will be back!"

includes taxes & fees

18 Dec - 19 Dec

"Very pleasant, comfortable and clean in a great location "

includes taxes & fees

15 Dec - 16 Dec

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 €271 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.

Recent reviews of Trappe properties

5/5 Excellent

"Very comfortable beds very clean nice people running the place really enjoyed it"

A verified traveller stayed at Quality Inn

Posted 22 hours ago

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 Cambridge Gem w/ Hot Tub, Pool & Dock!: This holiday home rental outside of Trappe is located on a lake, and has a fireplace, a balcony 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. You can relax into your holiday with a selection of games and 1 hot tub.

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 Bill Burton Fishing Pier State Park. In the wider area, you’ll find Long Wharf 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.

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Holiday Rentals in Trappe

Check Trappe holiday rental availability

Holiday Rentals in Trappe

Relaxing Waterfront Cottage Near St Michaels, Maryland

Walk to Everything House

Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

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

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

Eastern Shore Waterside Cottage Near St. Michaels

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

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Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Waterfront Getaway with Dock

Cottage on Cabin Creek

Bay Views & Fire Pit: Taylor’s Island Retreat

Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks

Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!

Autumn Charm Beautiful Waterfront Retreat Near Historic St. Michaels & Royal Oak

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

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F

Other types of properties in Trappe you may be interested in

Hyatt Regency Chesapeake Bay

Inn at Perry Cabin

St Michaels Inn

Find out more about Trappe

Recent reviews of Trappe properties

Quality Inn

Fairfield Inn & Suites by Marriott Easton

Best Western Plus Easton Inn & Suites

St Michaels Inn

Hyatt Regency Chesapeake Bay

The Wildset

Hampton Inn Easton

Holiday Inn Express Cambridge, an IHG Hotel

Days Inn by Wyndham Easton

Frequently asked questions