Trappe Vacation Rentals

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Check prices for these dates

Tonight
Nov 24 - Nov 25
Tomorrow
Nov 25 - Nov 26
This weekend
Nov 28 - Nov 30
Next weekend
Dec 5 - Dec 7

Vacation Rentals in Trappe

House (4 Bedrooms) | Interior
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

3.0 star property
Trappe
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Outdoor dining
Downtown St. Michaels | Porch + Pet-Friendly

Downtown St. Michaels | Porch + Pet-Friendly

Saint Michaels
Downtown St. Michaels | Porch + Pet-Friendly
Exterior detail
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

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

Cambridge
10.0 out of 10, Exceptional, (15)
"Well equipped and super clean; great place!"
United States
Steve S.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Terrace/patio
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Cambridge
10.0 out of 10, Exceptional, (80)
"Great for 10 adults and 4 grandchildren!"
United States
Phil S.
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge
9.6 out of 10, Exceptional, (19)
"In town for a family wedding. This worked out perfectly. Would stay there again "
United States
Barbara V.
The price is ￥22,679
￥55,209 total
includes taxes & fees
Dec 8 - Dec 9
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

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

St Michaels
9.6 out of 10, Exceptional, (147)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
United States
maggie k.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Outdoor pool, a heated pool
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

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

Woolford
9.8 out of 10, Exceptional, (74)
"We enjoyed our stay in Woolford. The day was filled with fishing, swimming and boating. Thank you again for sharing your property with our family."
United States
Linda S.
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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

St. Michaels
9.8 out of 10, Exceptional, (44)
"Wonderful home in excellent location!!"
United States
Sydney S.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Exterior
Modern Flat in the Heart of St. Michaels – Walk Everywhere

Modern Flat in the Heart of St. Michaels – Walk Everywhere

Saint Michaels
10.0 out of 10, Exceptional, (54)
"Such a beautiful space in a perfect location! We were able to walk to everything — shops, restaurants, farmers market, waterfront, etc! Highly recommend!"
United States
Paige R.
Modern Flat in the Heart of St. Michaels – Walk Everywhere
Outdoor pool
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Cambridge
9.8 out of 10, Exceptional, (7)
"Great House "
United States
Conrad L.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Interior
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

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

Stevensville
10.0 out of 10, Exceptional, (56)
"It’s a fantastic property!! Perfect for a getaway weekend. Everything was as described. A great place to stay home and enjoy all the amenities."
United States
Kurt H.
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

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

Saint Michaels
9.6 out of 10, Exceptional, (124)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
United States
Meghan K.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Fridge, microwave, oven, stovetop
The Middle Point Cabin in Saint Michaels

The Middle Point Cabin in Saint Michaels

Neavitt
9.8 out of 10, Exceptional, (56)
"We had a great stay. The cottage is just like the pictures. Nice area…lots of things to do."
United States
Michael
The Middle Point Cabin in Saint Michaels
Terrace/patio
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

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

Cambridge
9.8 out of 10, Exceptional, (133)
"This was our second time staying here. Love the location and size of the property. Plenty of space for the kids to play catch, ride bikes, and lots of crabbing and fishing. "
United States
Joe B.
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Private beach
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

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

Sherwood
10.0 out of 10, Exceptional, (20)
"Fantastic property"
United States
Harvey W.
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Exterior
Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

Cambridge
10.0 out of 10, Exceptional, (264)
"The property, house and amenities were exactly as described. Absolutely gorgeous views second only to the hospitality extended by Rob and Clarissa!"
United States
Tom K.
Family and Pet-Friendly, Waterfront with Pier
Marina
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

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

St Michaels
9.6 out of 10, Exceptional, (125)
"Beautiful little cottage! Location is perfect."
United States
John B.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Marina
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Tilghman Island
10.0 out of 10, Exceptional, (14)
"We had a wonderful stay at the Point of a View Cottage! The views are spectacular and we also enjoyed how easy it was to walk to places to eat and the local market. Recommendations for places to eat were spot on and also appreciated a message over the weekend notifying us of the local craft market held Sunday morning. Would love to come again one day! "
United States
Jennifer L.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Marina
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

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

Easton
10.0 out of 10, Exceptional, (95)
"Gorgeous views and surroundings"
United States
Robin P.
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
Outdoor dining
Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views

Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views

Tilghman Island
9.8 out of 10, Exceptional, (10)
"Great property!!! Absolutely would recommend!"
United States
John and Michele E.
Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views
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

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

10/10 Excellent
"We loved our room!! Very clean, relaxing, the front office was great, waterview, restaurant right next door within walking distance!! Great place to stay in Tilghman Island. Plus a nice continental breakfast with good coffee!! "
BETTY 1-night trip
Posted 1 day ago
Knapps Narrows Marina & Inn

Find out more about Trappe

Search for holiday rentals in Trappe on Expedia! You can easily find your home rentals, villas, holiday apartments in Trappe using one of the methods below:

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Look no further and take a look at our great range of rental properties in Trappe!

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?

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock: You might want to consider this vacation home rental near Trappe, which is located on a river and has an outdoor pool, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade game room.

How many vacation rentals will I find in Trappe?

With 4 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 Gerry Boyle Park at Great Marsh. In the larger area, you’ll find Bill Burton Fishing Pier State 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.