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Check prices for these dates

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Aug 8 - Aug 10
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Aug 29 - Aug 31
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Sep 26 - Sep 28

Browse Select Trappe Vacation Homes

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.8 out of 10, Exceptional, (11)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is CA $386
CA $697 total
includes taxes & fees
Sep 1 - Sep 2
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Outdoor pool

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

10.0 out of 10, Exceptional, (133)
"Great location and property. And epic crabbing to top it off!"
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Marina

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

9.4 out of 10, Exceptional, (28)
"I cannot say enough about this property. Home was so spacious, views were wonderful, kitchen was very well stocked and just minutes to town. Highly recommend renting this home."
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Rising Sun Bay View Cottage
Terrace/patio

Rising Sun Bay View Cottage

10.0 out of 10, Exceptional, (1)
"What a great location for an awesome vacation rental. The three floors of the house is amazing and the views of the bay a huge added bonus. The house is well equipped, and you can tell that the owners stay there part time.The layout allows for socializing and fun on the middle level with a sitting areas and screened in porch while others can find some peace and quiet if needed on the upper or lower floorsThe private beach access is awesome and a true benefit. Will look to find this place again...
Rising Sun Bay View Cottage
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Terrace/patio

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

9.8 out of 10, Exceptional, (128)
"We had a wonderful long weekend here. Perfect weather let us swim and kayak and fish all weekend. House was spacious enough for two families of five plus our dog. The views were perfect!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
St. Michaels Waterfront Home
Property grounds

St. Michaels Waterfront Home

9.8 out of 10, Exceptional, (31)
"We had a wonderful stay. Check in and out was very easy. The place was clean and well maintained. Very peaceful spot on the water. "
St. Michaels Waterfront Home
Beautiful Waterfront Retreat in Cambridge!
Interior

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (42)
"Our kids enjoyed the games in the crab house. It was great being able to use the kayaks and life vests."
The price is CA $354
CA $679 total
includes taxes & fees
Aug 11 - Aug 12
Beautiful Waterfront Retreat in Cambridge!
Waterfront Sunset Bayview: sleeps 6
Terrace/patio

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (19)
"Loved the location, the property, and amenities. Would definitely stay again!"
Waterfront Sunset Bayview: sleeps 6
The Blackwater refuge country house on a quiet 12 acres
Property grounds

The Blackwater refuge country house on a quiet 12 acres

9.8 out of 10, Exceptional, (10)
"Very happy with this place, quiet, clean, all good. "
The Blackwater refuge country house on a quiet 12 acres
Peaceful Queenstown Home w/ Deck & Grill!
Interior

Peaceful Queenstown Home w/ Deck & Grill!

9.6 out of 10, Exceptional, (9)
"Very cozy, a very quiet home"
Peaceful Queenstown Home w/ Deck & Grill!
RELAX- Eastern Shore Creek Home - 6 Guests
Smart TV, fireplace

RELAX- Eastern Shore Creek Home - 6 Guests

10.0 out of 10, Exceptional, (2)
"Great property that is well kept. It is a short drive to several wonderful restaurants and an outlet shopping center."
RELAX- Eastern Shore Creek Home - 6 Guests
Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18
Fridge, microwave, oven, stovetop

Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18

10.0 out of 10, Exceptional, (77)
"We were very impressed with the property and your place was very clean and had just about everything we needed. The location is wonderful and close to the event that we stayed in Cambridge for. I would definitely recommend this for others and will likely be renting again"
Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18
Heated pool, sandy beach, pier, and playground set punch point apart!
Beach nearby, sun loungers, beach towels

Heated pool, sandy beach, pier, and playground set punch point apart!

10.0 out of 10, Exceptional, (8)
"Beautifully decorated, peaceful, well appointed home for our girls bday celebration. Highly recommend."
Heated pool, sandy beach, pier, and playground set punch point apart!
Waterfront Getaway with Dock
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (45)
"Fit all of our needs. Clean,well furnished, nice kitchen. Stayed there twice and will probably go back."
The price is CA $317
CA $384 total
includes taxes & fees
Aug 13 - Aug 14
Waterfront Getaway with Dock
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
Outdoor dining

Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

10.0 out of 10, Exceptional, (8)
"My husband and I spent Christmas on Tilghman Island in this unique house right on the water. It was perfect for us to rest, relax and cook Christmas dinner. We enjoyed it so much we want to visit again when the boats are out. The yard was perfect for our dog to get some exercise. I can see this as a perfect place for family and friends in the summer."
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie
Exterior

Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie

10.0 out of 10, Exceptional, (16)
"We loved this home. The location is excellent--close to areas like Easton and St Michael's, but out of the way and secluded. We loved sitting on the lawn by the Dixon Creek and watching the sunset. House is well stocked, and wifi is strong--supported 3 people who had to work. Highly recommend this beautiful home."
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien
Interior

Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien

10.0 out of 10, Exceptional, (4)
"Very relaxing house to stay in. Plenty of room and well stocked kitchen . Close to St. Michaels and Cambridge. We were there for the Eagleman triathlon and we really enjoyed the seclusion. "
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien
Grasonville Home w/ Private Pool on the Water
Pool

Grasonville Home w/ Private Pool on the Water

10.0 out of 10, Exceptional, (21)
"Location was great for our stay"
Grasonville Home w/ Private Pool on the Water
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is CA $345
CA $577 total
includes taxes & fees
Aug 5 - Aug 6
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.
Outdoor pool

Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

10.0 out of 10, Exceptional, (6)
"This is such a special property. The house, the amenities and then the surprising foodie scene in Easton and St. Michael’s is within minutes. This is our second summer at this property and we are already starting to plan our third!"
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.
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

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

10/10 Excellent
"The bed was very comfortable and, the breakfast served in the morning was excellent!"
Lloyd 1-night trip
Posted 2 days ago
Comfort Inn & Suites Cambridge