Vacation rentals with a pool in Talbot County

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Popular amenities for Talbot County rentals with a pool

House rentals with a pool

Home in Stevensville
5 out of 5 average rating, 3 reviews

Waterfront Escape with Pool Nature Lover Paradise

KarenRating, 5 stars3 weeks ago
This property has a breathtakingly beautiful view of the water that has a fully fenced in yard…so you don’t have to worry about little ones getting into the water. The master bedroom and master bath was amazing. My extended family and I traveled from 4 different states to stay at this property and all of us were comfortable. The house had plenty of spaces to kit be on top of each other. I highly recommend booking this property. The host is very responsive and helpful. I will keep this property in mind for future stays.
Top guest favorite
A serene view of the Chesapeake Bay is captured from the backyard, featuring a pool surrounded by green lawn. Towering trees provide shade, while a patterned stone patio is visible in the foreground, enhancing the outdoor atmosphere.
Home in Chester
4.99 out of 5 average rating, 91 reviews

Waterfront Farmhouse Meets Modern Luxury

JayRating, 5 stars1 month ago
We had a wondferful time with extended family at this beautiful spot where you're surrounded by nature and expansive views from inside and outside the house. The views of the water and sunsets are breathtaking. The house has everything needed to cook family meals and share a comfortable and revitalizing time.
Home in Cambridge
4.67 out of 5 average rating, 6 reviews

Waterfront Cambridge Home: Pool & Dock!

DorindaRating, 5 stars4 months ago
We very much enjoyed our stay in Cambridge. My entire extended family stayed with us for my son's wedding and the house easily accomodated all 14 of us. The location was gorgeous - we enjoyed the dock and the views of the water. The location worked out extremely well - the home itself was private but was also located about 15 minutes from town and everything we could need including the wedding venue. I would note that if you visit in the winter and plan to use the sunroom or the bedroom upstairs with 2 beds to bring some extra blankets. It was quite cold our first night. The homeowner on the premise was gracious enough to bring us space heaters and that helped a ton - we were much warmer the 2nd night. I would definitely recommend this property and wish we had more time to stay and enjoy such a cute and unique home. Thank you for housing our entire crew for the wedding weekend! All of my family enjoyed the home and were all grateful to have beds!
Guest favorite
A spacious waterfront home is presented with a clear blue sky overhead. A well-maintained lawn surrounds a rectangular pool, with lounge chairs and umbrellas positioned nearby. The exterior features large windows and a covered porch, inviting relaxed outdoor living.
Home in Tilghman Island
4.97 out of 5 average rating, 30 reviews

Relax by the Water - Summer Dates Available!

RonnieRating, 5 stars3 months ago
Absolutely beautiful home! highly recommend!
A clear blue swimming pool is surrounded by a spacious patio, equipped with white lounge chairs and a table set for outdoor dining. A well-kept garden with green foliage is visible beyond the pool area, while a light-colored house with blue shutters stands in the background.
Home in Cambridge
4.95 out of 5 average rating, 20 reviews

Mill Street Cottage - A refreshing experience

WalterRating, 5 stars9 months ago
The house is wonderful, with master bedroom/bath and good smaller bedrooms and shared bath. A truly amazing swimming pool, where we spent a lot of time on the hot week of our stay. Meg made sure we got in ok, responded quickly to questions, and otherwise left us alone. Cambridge is an interesting town, with a good selection of restaurants - we ate out every night. We enjoyed the nearby Blackwater Wildlife Refuge from our car, but it also offers numerous biking, boating, and hiking opportunities. And yes, we played the games, from Taboo to Ping-Pong, available to us in the house. Overall, a sense of fun and kindness. We did not take full advantage of the kitchen, but it is well-equipped; you could make a big meal there as easily as at home. We had a lovely stay.
A clear swimming pool is surrounded by a wooden deck, featuring lounge chairs and a yellow inflatable float. The property includes a spacious house in the background, framed by lush greenery and trees, creating a relaxed outdoor atmosphere.
Home in Tilghman
5 out of 5 average rating, 3 reviews

Clearview | an ESVR property

TomRating, 5 stars34 months ago
fantastic spot on the Island. incredible sunsets. very clean with stunning views of the Bay. everything you need to enjoy the Island is here with walking distance general store.
Guest favorite
An inground pool is surrounded by a concrete deck, with a bright blue surface reflecting sunlight. Lounge chairs are positioned nearby, and a covered porch is visible in the background, providing a space for relaxation. Lush green lawns frame the pool area.
Home in Cambridge
5 out of 5 average rating, 10 reviews

"Goose Landing" Waterfront Retreat

JohnRating, 5 stars8 months ago
This was a great vacation. This place has it all from the pool to the kayaking, fishing, crabbing and the late night fires were we all just sat around the fire and enjoyed the time together. The house was awesome, plenty of room for all. The family had a great time. Definitely would rent this place again.

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