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

"Nice location down town. House was just as the pictures showed. "

"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!!!"

"We just finished a great three day stay at this property. The place was spotless and the location to the towns of the eastern shore was perfect. Wonderful to look out and see the river lazily roll by. The"

"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! "

"Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway...

Cambridge Vacation Rental | 7BR | 5.5BA | Stairs Required | 10,333 Sq Ft

"Terrific house, beautiful scenery, property management was very responsive and helpful. Would stay again. Thank you. "

"Nice place "

"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."

Taylors Island Vacation Rental | 3BR | 2.5BA | 2,100 Sq Ft | 1-2 Steps Required

"The house had a beautiful view. It was well stocked. Management was very responsive. Enjoyed a nice Thanksgiving with beautiful sunsets. Very private. Loved every aspect."

"The Ranch at Royal Oak was a fantastic property. The property was exactly as advertised - gorgeous waterfront estate with a large lawn. Incredibly peaceful. We were looking for a getaway to hit pause and just relax and the ranch Royal Oak was exactly what we needed. Marissa was a great host - incredibly responsive, check in instructions are very clear.and easy to follow. I highly recommend this property for your next getaway."

Grasonville Vacation Rental | 3BR | 2BA | Stairs Required for Access

"We started an annual tradition to rent this house with friends. Love the property, beautiful views and great location. Making great memories that will last a lifetime. Thank you for allowing us to use your beautiful home! :)"

"8 of us had a great time on Harris Creek in McDaniel, MD. Pulled our boats up to private dock and crabbing in minutes. "

"Our extended family of nine spent a week at Warwick Farms in July, 2024. There was space for all of us to be together for meals, puzzles, movies, and games...and also plenty of room for us to spread out and do our own thing. The pool was wonderful, the view was amazing, and the amenities were superb. We appreciated the cleanliness, the plentiful towels, the wildlife sightings, and the availability of the kayaks, etc. We had one small issue during the stay, but the property manager and host...

"This property is a phenomenal place to spend time with family and enjoy beautiful St. Michael’s. The house is well stocked and convenient to town. We’d love to come back. "

"Everything about this property was perfect for our family of 10 ranging in age from 79 to 2.5. The children loved the indoor and outdoor play areas, and it was hard to drag them away from the house for Thanksgiving dinner. The location was excellent for access to St Michael's and other spots on the eastern shore. The owner even helped us find a place to get fresh local oysters and shucking them was a family affair."

"Awesome place ! We had some family visit us there and everyone loved the place too. The toilet paper holder in the half bath needs to be reattached to the wall. Also … I noticed the drain pipe closest to the hot tub is separated at the top. "

"Beautiful house and location to getaway with peace and quiet. Still within 5-10 minutes of anything you need including downtown Cambridge. WillDefinitely come Back!"

AED 2,449 total

includes taxes & fees

26 Jan - 27 Jan

"We truly loved our stay! The home was super comfortable and well stocked for making Thanksgiving dinner for 6. We loved just looking out at the geese, swans and blue herons ! Really lovely. We’ll be back!"

"The property was perfect for our family get together. We had a baby, toddler, preschooler, elementary and teens, moms, dads and grandparents. There was a place for everyone. Having a pack n’ play available would have been nice, but we procured one elsewhere. The property was large and felt very private, but Cambridge was just a quick drive."

"Listing and photos accurately describe accommodations. We were comfortable and satisfied. A nice rural location for perusing outdoor activities - fishing, hunting, boating, paddling, birdwatching. Good parking for a boat trailer. "

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Other property types in Trappe

Front of house from St. Michaels harbor looking across Town Park

"The location couldn't have been more ideal. We were able to walk everywhere...all around town. And there was a beautiful view of the town park and the bay from the house. We were there for Christmas, visiting family, and her house was overflowing, so this was a little home-away-from-home. There were some difficulties. The shower curtain and main bath downstairs needs updating and the kitchen could be better appointed. The stairs to the king bed bedroom are, as others and the owner noted, very...