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Aug 22 - Aug 24
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Browse Select Trappe Vacation Homes

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, (10)
"Beautifully decorated, peaceful, well appointed home for our girls bday celebration. Highly recommend."
Heated pool, sandy beach, pier, and playground set punch point apart!
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, (130)
"Great house, host and location. Stayed with a larger group and plenty of room!"
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
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 $262
CA $565 total
includes taxes & fees
Aug 26 - Aug 27
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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, (40)
"Property was perfect for our family stay. House was clean and well stocked."
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Beautiful Waterfront Retreat in Cambridge!
Interior

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (43)
"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 $379
CA $696 total
includes taxes & fees
Sep 7 - Sep 8
Beautiful Waterfront Retreat in Cambridge!
Riverfront Denton Estate on 7 Acres w/ Fire Pit!
Interior

Riverfront Denton Estate on 7 Acres w/ Fire Pit!

2.0 star property
10.0 out of 10, Exceptional, (10)
"The family gathered here for a memorial service in Denton. The lovely property made all the difference. Everything was there and everything went so smoothly. We also enjoyed a spectacular sunset."
Riverfront Denton Estate on 7 Acres w/ Fire Pit!
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
Waterfront Cottage | Dock, Fire Pit & Pet-Friendly
Dining

Waterfront Cottage | Dock, Fire Pit & Pet-Friendly

10.0 out of 10, Exceptional, (32)
"This beautiful home was wonderful for our long overdue vacation - We loved our stay here very much - The town is amazing "
Waterfront Cottage | Dock, Fire Pit & Pet-Friendly
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!
Walk to Everything House
Fridge, microwave, oven, stovetop

Walk to Everything House

10.0 out of 10, Exceptional, (81)
"Clean and nice place to stay"
Walk to Everything House
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
Outdoor dining

Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

10.0 out of 10, Exceptional, (9)
"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
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Interior

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

2.0 star property
8.4 out of 10, Very good, (6)
"House was spacious plenty of room, great amenities, and very clean! "
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
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
Charming Waterfront Stay close to St. Michaels
Terrace/patio

Charming Waterfront Stay close to St. Michaels

9.8 out of 10, Exceptional, (12)
"Great house, updated, amazing views "
Charming Waterfront Stay close to St. Michaels
Thorneton Point Estate
Interior

Thorneton Point Estate

9.8 out of 10, Exceptional, (19)
"Beautiful, well-maintained property in a gorgeous waterside setting. "
Thorneton Point Estate
Time Stands Still, While Memories Are Made.
Private beach

Time Stands Still, While Memories Are Made.

10.0 out of 10, Exceptional, (14)
"Gorgeous views and location. "
Time Stands Still, While Memories Are Made.
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

St Michaels Inn

St Michaels Inn

10/10 Excellent
"The staff was very pleasant and accommodating. They greet with a smile and did everything possible to make our stay a good one. The breakfast was very nice. We loved the outside area with tables and seating so we could eat there etc. Parking was free and easy. The room was nice. decent size refrigerator."
BONNIE 2-night trip
Posted 2 days ago
St Michaels Inn