Trappe Vacation Rentals

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Vacation Rentals in Trappe

Property grounds
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
10.0 out of 10, Exceptional, (151)
"Quaint yet period correct. Plenty of room with decent kitchen. Especially love location and screaned back porch. Have stayed in house several times and does not disappoint!! Will go again for sure!"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Fridge, microwave, oven, stovetop
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
10.0 out of 10, Exceptional, (31)
"One of the best properties I have stayed at. With all the amenities, you never need to leave the home. We enjoyed the views, the quietness of the area, and the wildlife. We nicknamed two beautiful ducks…Sonny and Cher! The house is very clean, the checkin checkout procedures were very easy. The host communicated all the details plus additional suggestions. We are definitely returning very soon."
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
Interior
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
10.0 out of 10, Exceptional, (6)
"My sisters and I (5 total) visited in early November. Kent Island Time was a perfect fit. We were impressed by the cleanliness, spacious rooms, and well-equipped common areas. The best feature was the waterfront location. Even in November, we were able to sit outside on the patio and enjoy a glass of wine as we watched the amazing sunset. We all agreed we would absolutely stay again in the future."
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
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Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, (61)
"The house was lovely. We had 3 days of rain but the view and the beach made it interesting at all times. The hosts make sure you have everything you need for your comfort and entertainment. This is by far the best appointed house we have rented. Thank you for a wonderful week!"
Mid-Century Modern and Marvelous on the Bay
Terrace/patio
Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, (5)
"We loved Waterside Cottage. It was so quite & the crabbing was wonderful which is what we were looking for. Topher was wonderful to work with both before we arrived & on the day of arrival. My husband is already asking if we can book it again next year."
Eastern Shore Waterside Cottage Near St. Michaels
Pool
Bay Views |Breezy point Beach: 4BD 2BA King bed
10.0 out of 10, Exceptional, (1)
"The house was clean and quiet. The hosts were helpful and available for communication. This is a lovely house for a vacation away from crowds and by the beach."
The price is CA $233
CA $663 total
includes taxes & fees
May 22 - May 23
Bay Views |Breezy point Beach: 4BD 2BA King bed
Pool
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
10.0 out of 10, Exceptional, (1)
"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."
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
Fridge, microwave, oven, stovetop
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (16)
"We had a very enjoyable and relaxing stay here for Mother's Day weekend, coming in from DC. The property is in a great spot on the water and is a short ride into town. The house itself is cozy, clean, and welcoming with everything you need (including the crab house out back, which our four year old loved!) Rebecca is a thoughtful and accommodating host, too. She gave us several recommendations for food in the area and we really enjoyed her suggested restaurants in Cambridge and in Easton on the...
The price is CA $359
CA $642 total
includes taxes & fees
May 27 - May 28
Beautiful Waterfront Retreat in Cambridge!
Pool
Breathtaking Waterfront Estate
10.0 out of 10, Exceptional, (65)
"The home was spacious and beautifully decorated. Games and bikes and outside fire were perfect for family time. Beautiful scenery and privacy. A perfect stay."
Breathtaking Waterfront Estate
Outdoor pool
New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks.
10.0 out of 10, Exceptional, (126)
"While we wished for weather that was slightly better, we still enjoyed every minute of our 3 days. The weather didn't stop us from using the Kayaks or trying to catch a crab or two. the yard was perfect for exercising the kids and the puppies. It was a short easy drive into town, for some shopping, eating and even a visit to a rum distillery. The wineries were all closed at the beginning of the week this time of year. The house was supplied with everything we needed. The listing was spot on,...
New St. Michaels estate -Pier,Pool, Gas fire pit, Bikes & Kayaks.
Fridge, microwave, oven, stovetop
Tidal Serenity- Remote Waterfront Home with dock
10.0 out of 10, Exceptional, (15)
"Your Tidal Serenity home is a dream come true! Our stay was an incredible nature experience. The house was clean and comfy and the dock was the perfect centerpiece for adventure and fun. We kayaked, crabbed, fished and spotted a TON of amazing birds. We visited Blackwater Bakery in Cambridge, Emily’s Farm, Blackwater National Refuge and Harriet Tubman’s Underground Railroad National Park and mostly-hung around the property exploring Taylor’s island on bike and foot. We hope to visit...
Tidal Serenity- Remote Waterfront Home with dock
Property grounds
St. Michaels Waterfront Home
10.0 out of 10, Exceptional, (20)
"Beautiful house, perfect for a weekend getaway with young kids. The host was very helpful!"
St. Michaels Waterfront Home
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (25)
"My family and I enjoyed our stay at the Carpenter Alley Cottage in Saint Michaels! The location was perfect -- walking distance from everything! Appreciated that there was a ground floor bedroom for my parents so they didn't have to climb the stairs and my daughter loved having her own bunk bed room! I did have a few questions about the cottage and the check-in process and my inquiries were all met with a prompt response. Would love to stay here again! (One note though is that it is a smaller,...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop
The Middle Point Cabin in Saint Michaels
9.8 out of 10, Exceptional, (47)
"Looked just like the pictures. Everything was new clean and comfortable. Enclosed patio was a hit with our cat."
The Middle Point Cabin in Saint Michaels
Beach nearby
Waterfront, cozy cottage with private pool on 27 acres of privacy
9.8 out of 10, Exceptional, (85)
"We came for the Ironman 140.6 and we lucked out finding this lovely cottage! It was the perfect location, the property was beautful, and the house was very clean and had everything we needed. Dave and Cindy were so kind and helpful! They welcomed us to the property, gave us restaurant recommendations, let us pick some figs, and were very helpful when I left something behind. We would love to stay again!"
Waterfront, cozy cottage with private pool on 27 acres of privacy
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (196)
"We came here for the St. Michaels Running Festival. The location was perfect for navigating the morning race traffic. It was also the perfect spot to avoid the extra foot traffic. We will definitely be back."
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, (66)
"What a beautiful property! We did a quick couples getaway and couldn’t have had a nicer weekend. The house is a beautiful, wraparound porch country home. Floorplan was really well designed and the decor was spot on. Looking forward to coming back next fall as well!"
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Beach
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
9.8 out of 10, Exceptional, (51)
"We have enjoyed our stay at the property, everything was very nice and spacious away from everything, just the way we wanted. Our only issue was the landscaping work being done for 2 days of our stay, my son has allergies on cut grass and he ended up staying indoor for the most of those days."
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
Property grounds
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (106)
"Wonderful return visit to St Michaels. This time at a fantastic historical home in perfect location. Home was everything you could ask for and more. Park your car and walk anywhere, within a very quiet neighborhood, yet minutes from all St Michaels offers. Highly recommend this Property and host."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Fridge, microwave, stovetop, dishwasher
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (4)
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Don't see what you're looking for?
See all available properties in Trappe
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.

Trappe Vacation Rental Travel Info

Number of vacation rentals
5
Popular accommodation
Trappe private vacation homes
Known landmarks
Avalon Theatre, Bill Burton Fishing Pier State Park and Academy of the Arts
International airport
Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)

Other types of properties in Trappe you may be interested in

Exterior
Best Western Plus Easton Inn & Suites
2.5 star property
9.4 out of 10, Exceptional, (1010)
"Beautiful area, nice staff, great free breakfast and big room. "
The price is CA $176
CA $193 total
includes taxes & fees
May 27 - May 28
Best Western Plus Easton Inn & Suites
Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers
Hyatt Regency Chesapeake Bay
4.0 star property
8.8 out of 10, Excellent, (1002)
"Gorgeous property. Beautiful views. Well maintained and kept clean. The bed was the best lullaby ever. I slept ever so soundly. Breakfast was bountiful and delicious. The young lady that checked us in was on the surly side and could use some professional development on friendliness and hospitality for people of all cultures. But, the gentleman from Ghana that check me out made up for what she lacked and redeemed my experience. I would definitely stay again. "
The price is CA $244
CA $334 total
includes taxes & fees
May 22 - May 23
Hyatt Regency Chesapeake Bay
Front of property
St Michaels Inn
2.5 star property
8.2 out of 10, Very good, (1005)
"The staff was frieendly and very helpful, and the motel was very nice. The only issue I had with the stay was the high sulfur content of the water. It stank, and that's quite unpleasant."
The price is CA $124
CA $136 total
includes taxes & fees
Jun 3 - Jun 4
St Michaels Inn
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.

Everything you need to know about Trappe vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Trappe vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Trappe vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Trappe vacation rentals we have selected for you start as low as CA $233 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 vacation 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 vacation.

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 vacation rental in Trappe?

Yes, we give you a choice of vacation rentals near popular attractions in Trappe, or you can choose a more remote option if you're looking for a relaxing stay. Trappe is known for its waterfront and parks.

What's the top vacation rental in Trappe?

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife: Visitors like this Trappe vacation home rental. It offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Trappe?

With 3 Expedia vacation rentals, you're sure 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 larger area, you’ll find Long Wharf Park and Choptank River Lighthouse.

What’s a vacation rental in Trappe like?

Vacation rentals are privately owned properties you can book for a couple of days or more in Trappe. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for small groups.

Recent reviews of Trappe properties
Expedia verified reviews

The Wildset

The Wildset

5/5 Excellent
"This spot was absolutely perfect for our weekend. We ran a running race that went through town so this was a central location. The finishes are top of the line. The beds are unbelievably comfortable and the staff was so so accommodating. It’s absolutely perfect. Can’t wait to go back!"
A verified traveller stayed at The Wildset
Posted 2 days ago
The Wildset