Trappe Holiday Rentals

Holiday Rentals in Trappe

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Fridge, microwave, stovetop, dishwasher
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, 4 reviews
"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!
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, 105 reviews
"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
Fridge, microwave, oven, stovetop
Walk to Everything House
10.0 out of 10, Exceptional, 64 reviews
"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!
Fridge, microwave, oven, stovetop
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, 17 reviews
"We enjoyed our trip, the house was fully equipped and had all the comforts you could need. The water view, watching the birds, the kayak, the dock at sunrise, were our favorite things. We look forward to coming back sometime soon."
The price is AU$777
per night
16 June - 17 June
Beautiful Waterfront Retreat in Cambridge!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Property grounds
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, 108 reviews
"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
Property grounds
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
10.0 out of 10, Exceptional, 152 reviews
"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
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, 197 reviews
"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
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, 127 reviews
"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
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, 27 reviews
"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
Property grounds
Mid-Century Modern and Marvelous on the Bay
10.0 out of 10, Exceptional, 61 reviews
"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
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Pool
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
10.0 out of 10, Exceptional, 1 review
"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."
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
Pool
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
10.0 out of 10, Exceptional, 1 review
"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
Exterior
Dollhouse in Central Historic St Michaels
9.8 out of 10, Exceptional, 38 reviews
"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
Property grounds
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
10.0 out of 10, Exceptional, 1 review
"Property and location couldn't be better! Host was very accommodating and quick to respond. Will definitely go back!"
The price is AU$614
per night
10 June - 11 June
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Waterfront, cozy cottage with private pool on 27 acres of privacy
Beach nearby
Waterfront, cozy cottage with private pool on 27 acres of privacy
9.8 out of 10, Exceptional, 85 reviews
"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
Fridge, microwave, oven, stovetop
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
10.0 out of 10, Exceptional, 31 reviews
"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
Smart TV, books, printers
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
10.0 out of 10, Exceptional, 5 reviews
"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
Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, 25 reviews
"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 AU$407
per night
10 June - 11 June
Waterfront Getaway with Dock
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Lake
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, 67 reviews
"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
Fridge, microwave, oven, stovetop
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
9.6 out of 10, Exceptional, 4 reviews
"Nice place for a getaway."
The price is AU$1,395
per night
9 June - 10 June
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
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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 Holiday Home Travel Info

Number of holiday homes
5
Popular accommodation
Trappe private holiday 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

Hyatt Regency Chesapeake Bay
Indoor pool, 2 outdoor pools, pool umbrellas, pool loungers
Hyatt Regency Chesapeake Bay
4.0 star property
8.8 out of 10, Excellent, 1,009 reviews
"Gorgeous property!"
The price is AU$336
per night
8 July - 9 July
Hyatt Regency Chesapeake Bay
St Michaels Inn
Front of property
St Michaels Inn
2.5 star property
8.2 out of 10, Very good, 1,008 reviews
"A traditional, comfortable motel with a pleasant Chesapeake ambience. Feels like home."
The price is AU$230
per night
23 June - 24 June
St Michaels Inn
Inn at Perry Cabin
Breakfast, lunch, dinner served; sea views
Inn at Perry Cabin
5.0 star property
9.6 out of 10, Exceptional, 297 reviews
"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 AU$1,279
per night
13 June - 14 June
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.

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$407 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?

Beautiful Waterfront Retreat in Cambridge!: This holiday home rental outside Trappe is located on the waterfront, and has a selection of games, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Trappe?

With 3 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.

Recent reviews of Trappe properties
Expedia verified reviews

Days Inn by Wyndham Easton

Days Inn by Wyndham Easton

4/5 Good
"Was a smell in room. Was clean so I sprayed the room. Staff was helpful. Not bad for the money. "
A verified traveller from Fayetteville stayed at Days Inn by Wyndham Easton
Posted 1 day ago
Days Inn by Wyndham Easton