Trappe Vacation Rentals

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Vacation Rentals in Trappe

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!
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (105)
"This is our third visit. You can’t have a better location! We love St. Michael’s and this historical cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Walk to Everything House
10.0 out of 10, Exceptional, (64)
"The house was perfectly located in town in St. Michael’s with off street parking as a bonus. Despite the weather being cold and rainy, we had a lovely time in charming St. Michaels. It was a delightful spot for our annual girls weekend."
Walk to Everything House
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Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (17)
"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 $399
CA $691 total
includes taxes & fees
Jun 16 - Jun 17
Beautiful Waterfront Retreat in Cambridge!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (108)
"VRBO link hasn’t enabled me to communicate with property manger/owner as I’m unable to access account via the VRBO link. I’ve re-registered multiple times now."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
10.0 out of 10, Exceptional, (152)
"Cute, quaint, conveniently located home. Lovely stay!"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (197)
"We had our boat with us. Split out time between being on the water and going into St Michaels"
Relaxing Waterfront Cottage Near St Michaels, Maryland
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (127)
"The house looked better than the pictures. It was very cozy and had everything we needed. It’s probably the best location for walking around town. Water pressure in the shower was decent, and the beds were comfortable."
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (27)
"The house was perfect for our needs. It has a cute, fenced in yard so our 2 dogs could hang outside. It had everything we needed for a wonderful weekend birthday celebration!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
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
Family Beach House: Spacious Deck, Grill & Views
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."
Family Beach House: Spacious Deck, Grill & Views
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
Dollhouse in Central Historic St Michaels
9.8 out of 10, Exceptional, (38)
"Cute little place close to town. Perfect for what we wanted."
Dollhouse in Central Historic St Michaels
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
10.0 out of 10, Exceptional, (1)
"Property and location couldn't be better! Host was very accommodating and quick to respond. Will definitely go back!"
The price is CA $248
CA $550 total
includes taxes & fees
Jun 10 - Jun 11
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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
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
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
10.0 out of 10, Exceptional, (5)
"We had a lovely stay at The Blue Heron. We had a retreat scheduled with friends that we had to relocate last minute due to snow in western Maryland. We stumbled upon this listing, and the home was perfect for our needs. Plenty of beds, fully stocked kitchen, several rooms and couches for those who wanted to read, others to play games, and others to watch football playoffs on tv. The best part of the house was the dining room table that could seat up to 18 (?). It was nice to be able to not have...
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (25)
"We loved the proterty! House was set up with pleanty of room for 4 of us. It was clean and comfortable. Out back was very private. Would definitely stay here again. We had a blast!"
The price is CA $301
CA $362 total
includes taxes & fees
Jun 10 - Jun 11
Waterfront Getaway with Dock
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, (67)
"Wonderful house. Well stocked with supplies. Great open floor plan along with a couple separate spaces on the main floor. Our group had 7 adults and our eight grandchildren six and under. Pool has gated access which was a key feature with all our little ones. The owner provided much info regarding things to do in the area. The bedroom spaces worked out great with our mix. We really enjoyed the crab traps and the dock for fishing. It was mostly casting practice but the kids loved it. We enjoyed...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
9.6 out of 10, Exceptional, (4)
"Nice place for a getaway."
The price is CA $615
CA $1,240 total
includes taxes & fees
Jun 9 - Jun 10
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
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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

Other types of properties in Trappe you may be interested in

Hyatt Regency Chesapeake Bay
4.0 star property
8.8 out of 10, Excellent, (1009)
"Gorgeous property!"
The price is CA $258
CA $350 total
includes taxes & fees
Jul 8 - Jul 9
Hyatt Regency Chesapeake Bay
St Michaels Inn
2.5 star property
8.2 out of 10, Very good, (1008)
"Toilet seat was pealing. Bathroom floor needed a scrub."
The price is CA $188
CA $207 total
includes taxes & fees
Jun 23 - Jun 24
St Michaels Inn
Inn at Perry Cabin
5.0 star property
9.6 out of 10, Exceptional, (297)
"The property is beautiful, with terrific gardens and magnificent water views. Our room (06) was waterfront with huge hydrangeas outside. However, the bathroom needs renovation. The pedestal sink was awful as there was no place for cosmetics or the cosmetic bag. An upright suitcase on wheels was brought into the bathroom to provide a needed serface. The soaking tub had a smallish glass "shower curtain" so the floor was a bit moist after showering. The bed creaked with every movement, the...
The price is CA $943
CA $1,141 total
includes taxes & fees
Jun 10 - Jun 11
Inn at Perry Cabin
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Trappe. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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: You might want to consider this vacation rental near Trappe, which 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.

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