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Compare 186 Vacation Homes in Trappe with updated reviews, rates, and availability.

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Enjoy the sunset from Long Wharf Marina across the street

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

10.0 out of 10, Exceptional, (6)
"This stay was perfect. The location was charming and safe, and the home was clean and cozy. Jennifer was a very accommodating and responsive host."
The price is SAR 657
SAR 1,473 total
includes taxes & fees
16 Dec - 17 Dec
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Exterior

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

2.0 star property
10.0 out of 10, Exceptional, (3)
"The house was very clean and was great for our home base while visiting family in St. Michael’s. The owner was very response and friendly. The house included all basic amenities and then some! The owner really took the time and care preparing this place for guests. Downtown Cambridge is a short drive and a cute little town with shops and restaurants. We didn’t have a ton of time to explore downtown but plan to on our next stay! "
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Living Area

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

9.8 out of 10, Exceptional, (32)
"We were able to walk to most places we wanted to go in town. The house was a little small but everything we needed was there and the property managers were easy to reach. We had a great time!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Beautiful Waterfront Retreat in Cambridge!
Exterior

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (31)
"This house exceeded our expectations in every way. The kitchen is large and well-appointed, the beds are comfortable, and the peace and quiet is priceless. We enjoyed morning coffee in the sunroom, table tennis in the crab house, sunsets from the dock, and stargazing at the firepit. If you desire peace and quiet this house is a perfect choice!"
The price is SAR 1,032
SAR 1,934 total
includes taxes & fees
1 Dec - 2 Dec
Beautiful Waterfront Retreat in Cambridge!
Walk to Everything House
Front of House

Walk to Everything House

10.0 out of 10, Exceptional, (72)
"We thoroughly enjoyed the convenience of walking to shops, restaurants, and waterfront! Residence was charming and clean! Only minor issue was we couldn’t locate the iron- just the ironing board! We still had fun but we’re just a bit wrinkled!😁"
Walk to Everything House
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Exterior

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

10.0 out of 10, Exceptional, (32)
"Perfect large space on a quiet and pretty area. Really great space. "
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Cottage on Cabin Creek
Beach

Cottage on Cabin Creek

10.0 out of 10, Exceptional, (100)
"I highly recommend staying here for a cozy couples weekend. It was absolutely beautiful and quiet. The host was so nice and made us feel welcome. I can’t wait to stay here again."
The price is SAR 939
SAR 1,361 total
includes taxes & fees
30 Nov - 1 Dec
Cottage on Cabin Creek
Grasonville Home w/ Private Pool on the Water
Grasonville Vacation Rental | 3BR | 2BA | Stairs Required for Access

Grasonville Home w/ Private Pool on the Water

9.8 out of 10, Exceptional, (19)
"We stayed at this place for a family wedding at the nearby beach club. In addition to be a convenient location, the views from the house and property were stunning. The style inside the house was quite eclectic which gave it wonderful charm. Coming back at night gave us fits trying to find the driveway but that was a small price to pay for such a great house. "
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, (8)
"Stayed here for a wedding was perfect for the group of 4 of us. Living room is bigger than it looks in the photos and the house was well kept/ clean. Host was great and responsive as well!"
The price is SAR 751
SAR 1,361 total
includes taxes & fees
25 Nov - 26 Nov
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Exterior

Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

9.6 out of 10, Exceptional, (19)
"The house was just as it was listed!! Our annual family vacation was so much fun here! Plenty of room, very clean, and fully stocked! Peddle boats, kayaks, and pool used daily!! Fire every night!!! Thank you for the wonderful hospitality!!!"
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!
Front of home with view of path to pier and dock

Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!

9.8 out of 10, Exceptional, (21)
"We went to this wonderful home for our 32nd wedding anniversary and it was so lovely. The home was so comfy and well stocked, the beds were very comfortable and the sunsets were spectacular. We enjoyed every minute! Barbara was just so delightful and helpful. She made everything perfect! Would love to stay again some time."
Waterfront - pier & acreage to run & play. Pet friendly Oct/Nov dates open!
Beautiful Peaceful Home
Living area

Beautiful Peaceful Home

7.4 out of 10, Good, (3)
"Owner canceled the day before with no notice"
Beautiful Peaceful Home
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)
"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
Mid-Century Modern and Marvelous on the Bay
Property grounds

Mid-Century Modern and Marvelous on the Bay

10.0 out of 10, Exceptional, (70)
"The house was amazing! From the moment the front door opened it was a visual feast. The views are incredible, it's quiet, private and very relaxing. There were personal elements reflecting the current and original owners which we found very interesting and the attention to detail throughout was superb! Everything was incredibly well stocked with a multitude of extras. "
Mid-Century Modern and Marvelous on the Bay
St. Michaels Waterfront Home
Property grounds

St. Michaels Waterfront Home

9.6 out of 10, Exceptional, (25)
"Excellent property ! Had everything we needed and wanted and more. Waterfront views and shorebirds beautiful ! We hope to revisit !!! "
St. Michaels Waterfront Home
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Aerial view

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

10.0 out of 10, Exceptional, (7)
"This house is huge and has lots of different indoor and outdoor gathering spaces so the kids and adults in our group of three families didn’t have to be on top of each other in one living space the whole time. Big firepit area and huge lawn were great, and we enjoyed the kayaks and canoe. There’s a place to buy fresh crabs, oysters, and shrimp very close by, and the house has everything you need for a crab night. The owner was incredibly responsive and kind."
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Private 9 acre Family Retreat on the Chesapeake Bay
Front of house

Private 9 acre Family Retreat on the Chesapeake Bay

10.0 out of 10, Exceptional, (8)
"Incredible sunset views, very nice location to relax, play games on the deck and enjoy time together with friends. A beautiful quiet setting."
Private 9 acre Family Retreat on the Chesapeake Bay
Bay Views & Fire Pit: Taylor’s Island Retreat
Taylors Island Vacation Rental | 3BR | 2.5BA | 2,100 Sq Ft | 1-2 Steps Required

Bay Views & Fire Pit: Taylor’s Island Retreat

9.8 out of 10, Exceptional, (10)
"This is a hidden jewel. We had so much fun fishing and crabbing. The home was everything you could ever ask for. We will definitely be back next year for a longer stay. If you are looking for some peace and quiet, this is the place to be. Thank you to the owners for making this a great place. "
Bay Views & Fire Pit: Taylor’s Island Retreat
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
Aerial view of property- river, dock, pergola , pool behind house

Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks

9.8 out of 10, Exceptional, (6)
"We enjoyed our time at the house very much. We went out to dinner only once and the rest of the time we ate in. We grilled two nights and made a roast one night. The views and the pool were more than you could imagine."
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
Pool

Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!

9.8 out of 10, Exceptional, (9)
"Our stay was amazing. The house is beautiful. The views and peaceful location were completely used. We had many fun game nights and dinners around the table, the kitchen easily provided many happy meals. The gas grill, the fire pit were easy to use. The kayaks were a lot of fun. Sitting on the dock enjoying the peaceful quiet mornings was rejuvenating. The pool chairs and umbrellas were really nice. A ping pong table in the garage was a ton of fun too. The extra fridge/freezer was handy and the...
Waterfront Retreat with a New in ground pool! The Eastern Shore at it's best!
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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Other property types in Trappe

Relaxing Waterfront Cottage Near St Michaels, Maryland
Charming Cottage on a quite creek of the Chesapeake Bay with private pool.

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (217)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
Walk to Everything House
Front of House

Walk to Everything House

10.0 out of 10, Exceptional, (72)
"We thoroughly enjoyed the convenience of walking to shops, restaurants, and waterfront! Residence was charming and clean! Only minor issue was we couldn’t locate the iron- just the ironing board! We still had fun but we’re just a bit wrinkled!😁"
Walk to Everything House
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
Nature,Outdoors,Scenery,Water,Waterfront

Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

10.0 out of 10, Exceptional, (4)
"We had the most wonderful time at this charming house on Tillman Island! While the pics are great, it is even better in person. The house is perfectly nestled on the waterway, offering stunning views. The backyard pool was a true highlight, and we spent countless hours splashing around, the pool in the sun."
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
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.