Vacation rentals with a pool in Columbia County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Columbia County rentals with a pool

House rentals with a pool

Superhost
Home in Old Chatham
4.93 out of 5 average rating, 29 reviews

Haddock + Cotter - Chic Farmhouse and Barn w/ Pool

IdaRating, 5 stars4 weeks ago
We had a good stay at Victoria’s farmhouse. The location is really peaceful and relaxing, surrounded by nature—perfect if you’re looking to unplug a bit. The house itself is beautiful and very comfortable, with unique interiors that feel like something out of a design magazine. Victoria was easy to communicate with and helpful when we had questions. It’s a bit off the beaten path, which we liked, but still just a 15-minute drive to shops and about 30 minutes to the train and some great restaurants in Hudson. Overall, a lovely spot for a quiet getaway.
Superhost
Home in Hudson
4.75 out of 5 average rating, 61 reviews

Modern Glass House

CelesteRating, 5 stars1 day ago
Stunning property! Had a great stay
Guest favorite
Home in Pine Plains
5 out of 5 average rating, 41 reviews

Stunningly Designed Luxury Home w/ Pool & Hot Tub

NaomiRating, 5 stars4 weeks ago
We had an amazing relaxing weekend. The beds are comfy, pool heated, quiet serene area. All around perfect weekend getaway. The house was clean and had everything we could have possibly needed.
Guest favorite
Home in Athens
4.93 out of 5 average rating, 43 reviews

Catskills Lake Community Escape near Hudson

TinaRating, 5 stars4 weeks ago
House is very comfortable and clean in a convenient location to Hudson and other local attractions. The host is very responsive, helpful and accommodating. There is the additional bonus of having access to the lake and the amenities in Sleepy Hollow community, but we were so busy with hiking, visiting a winery and dining at some great restaurants we didn’t use it! We had a really great long holiday weekend and would definitely recommend staying at this air bnb!
Top guest favorite
Home in Egremont
5 out of 5 average rating, 31 reviews

The Catamount Ski Haus w. Pool/Hot Tub

JulieRating, 5 stars4 weeks ago
This house was perfect for our needs. We were in town for Berkshires graduation. It was 15 min from the school and 15 min from Great Barrington. Wish the weather would have been better for the pool! They were very available for any of our questions and needs. Definitely recommend!
Guest favorite
Home in New Lebanon
4.98 out of 5 average rating, 60 reviews

Berkshire Mountain home views, pool, Queechy Lake

GeorgeRating, 5 stars4 months ago
The house was very spacious, the kids ranging from 6-10 loved the games, especially cue ball and fuzz ball. The adults loved the fact there was a lower half where the kids can watch movies and play, while the adults did grown up chatting in the living space. A memorable ski weekend that everyone enjoyed to the fulliest and sad it went so fast. We look forward returning one day in the spring or summer to see a different aspect of the area. Thank you!
Guest favorite
Home in Hudson
4.94 out of 5 average rating, 77 reviews

Hudson River Sunset Getaway

AmandaRating, 5 stars2 months ago
The view from this house is amazing and my family loved putting up the blinds every morning to gaze out. The sitting room and bedrooms were so lovely, homey, and comfortable to lounge in. Maura was welcoming and proactive in communication and had beautiful flowers waiting in the living room for us.
Top guest favorite
Home in Athens
4.96 out of 5 average rating, 53 reviews

Modern & Cozy Lake Oasis ~ Hot Tub ~ Games ~ View

DanielleRating, 5 stars2 weeks ago
We loved Kathryn’s place! It was so peaceful and pretty, we loved having lake access, and it was convenient to drive to several local towns with great restaurants. The whole family enjoyed the kayaks and the community pool and the lovely outdoor space. My favorite part of the stay was the friendly fox who would visit the property in the mornings. Kathryn was also a wonderful host and responsive to our questions/messages. I would definitely stay here again!

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