Vacation rentals with a pool in Dutchess County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Dutchess County rentals with a pool

House rentals with a pool

Guest favorite
Home in Hopewell Junction
4.96 out of 5 average rating, 26 reviews

Cabin Oasis in the Woods

MaximRating, 5 stars8 months ago
Really great place to get away from the city. Close to nature + fun things to do if thats your thing, and also well-equipped enough to just stay at home :)
Guest favorite
Home in Stanfordville
4.96 out of 5 average rating, 49 reviews

Charming lakeside cabin with private heated pool

JustinRating, 5 stars9 months ago
My family and I stayed for a long weekend and were so glad that we did! It’s a beautiful cabin, with all the things you need. Kitchen is stocked with essentials, enough bathrooms, beds are super comfortable, hooks to actually hang things like towels, jackets… but we loved the outdoors even more! We walked to the lake, spent way too many hours in the pool, grilled, lounged, made s’mores by the fire pit and watched the beautiful stars at night. Couldn’t ask for more. Paula and her lovely family are SO welcoming it’s crazy. 😂. Hope to be back next summer!
Superhost
Home in Millerton
4.88 out of 5 average rating, 26 reviews

Farmhouse with a view, hot tub, pool, and fire pit

PhuriRating, 5 stars3 weeks ago
Beautiful house with lots of greenery — very peaceful and relaxing. The pool and hot tub were a great bonus. The host was fantastic: easy to communicate with and very understanding. The weather wasn’t ideal, but everything else was great. Would definitely love to visit again!
Guest favorite
Home in Hopewell Junction
5 out of 5 average rating, 20 reviews

MCM in the Hudson Valley

LesleyRating, 5 stars3 weeks ago
We had a fantastic stay at this Airbnb! The place was impeccably clean and incredibly comfortable, making it a perfect retreat. The host was very responsive and helpful, addressing all our needs promptly. Highly recommend!
Guest favorite
Home in Holmes
4.91 out of 5 average rating, 11 reviews

Enchanted Escape | POOL, LAKE, Concierge Services

AnxhelaRating, 5 stars2 weeks ago
We had such a great experience staying at this Airbnb. The house was beautiful, super clean, and the view was just perfect honestly even better than the photos. What really made our stay stand out though was the host, Sunny. He was amazing so helpful, kind, and incredibly thoughtful. As a Muslim family, we really appreciated how respectful and considerate he was. He made sure we had our privacy and went out of his way to make everything as easy and comfortable as possible for us. It honestly felt like staying at a friend’s place. We’d definitely come back and highly recommend this spot to anyone looking for a peaceful, welcoming place to stay.
Guest favorite
Home in Highland
4.89 out of 5 average rating, 19 reviews

Hudson Valley Retreat w/ Pool

johnRating, 5 stars5 months ago
We had a wonderful stay at Zahra’s home. The home was just as described and was the perfect cozy sanctuary we needed. Nicely located and close to all . Appointed with all one could want for a month long stay. Zahra is truly a five star host and went well above, with quick responses and furnishing us with a tree for the holidays. Can’t recommend enough if you’re planning a trip to the Hudson Valley area.
Guest favorite
Home in Salt Point
5 out of 5 average rating, 28 reviews

Hudson Valley Paradise

MaureenRating, 5 stars2 weeks ago
The house is absolutely beautiful. Daniel has taken such good care in making this home unique with decorative style it is a real standout. The home is spacious, clean and so comfortable to stay in. The grounds are well kept. Nature is in full bloom, deer greeted us and so many beautiful birds and flowers. This house is a true gem in the area.
Top guest favorite
Home in Lagrangeville
5 out of 5 average rating, 34 reviews

Hudson Valley Colonial with Inground Pool

ChelseaRating, 5 stars1 week ago
Kathleens place was perfect for our friends and family weekend vacation upstate. The house and property was absolutely stunning and fit our group of 10 so comfortably. We were talking about our next stay there before we even left. Highly recommend!

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