Holiday rentals with a pool in Catskill Mountains

Find and book unique homes with a pool on Airbnb

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Popular amenities for Catskill Mountains rentals with a pool

House rentals with a pool

Top Guest favourite
Home in Catskill
5 out of 5 average rating, 19 reviews

NEW! Catskill Family Hideout with Seasonal Pool

DeborahRating, 5 stars1 month ago
What a great spacious home. Plenty of room for the whole family. Clean and neat! Beds were super comfortable! Great water pressure. Beautiful back yard and three season porch. This was our second visit here and it was just as great as the first!!
Guest favourite
Home in Newburgh
4.87 out of 5 average rating, 79 reviews

Entire Home (private pool), Event Friendly

EastonRating, 5 stars2 days ago
The house is very clean, the host was very responsive at a fast rate. Was flexible with our check-in time. The house was awesome in general. We are definitely coming back.
Guest favourite
Home in New Paltz
4.93 out of 5 average rating, 133 reviews

Harrison Field Pool Hiking BikeRailTrail 2 Town

AlannaRating, 5 stars5 months ago
We had a great weekend celebrating our parents anniversary. The house was plenty big for all of us and the grounds are beautiful. Nathan was quick to respond when we had trouble navigating the AC and made sure we enjoyed our stay!
Superhost
Home in Grahamsville
4.89 out of 5 average rating, 91 reviews

Spacious Catskills Farmhouse w/ In-Ground Pool!

AnnRating, 5 stars1 month ago
This is a beautiful old house with huge windows and tons of light, beautiful views, and lots of bedrooms and hang out areas so everyone has space. The kitchen had everything we needed, the beds were comfortable and the entire place was super clean and tidy. There was a good selection of games we could play and music that our family enjoyed. It was also so nice that the house was pet friendly. The only downside was that the house was quite close to the road and my kids really wanted to sled down the hill in the backyard, but there was nothing to stop them from sliding into the road. There is hardly any traffic on the road, though, so noise was not an issue. We really enjoyed our stay here! Definitely recommend for big groups or families. We are a 7 person family - teenage kids, parents, grandparents.
Guest favourite
Home in Saugerties
4.86 out of 5 average rating, 86 reviews

Unique Contemporary on 40 Pvt Ac, Enclosed Hot Tub

NadineRating, 5 stars1 month ago
Such a great experience that reaffirms how hard hosts work! Robyn communicated the weather problems in advance and let us know things might be iffy getting in because of a winter storm. Instead of just making sure the home itself was pristine, relaxing, and totally picturesque, she made sure our arrival was perfect. Snow plowed, everything iced, bag of goodies hung up on our arrival. It was such incredible, flexible caretaking of the property and the guests! Besides that, onto the regular stuff- awesome kitchen, hot tub, bedrooms, everything super clean. Was a perfect winter stay!
Guest favourite
Home in Preston-Potter Hollow
4.91 out of 5 average rating, 32 reviews

Catskill Home w/ Sauna, by ski &Mountain view

DavidRating, 5 stars2 months ago
Thank you so much for hosting us. Our family truly appreciated the easy access and the prompt responses to any questions we had. We had a wonderful time staying at the house and really enjoyed using the sauna. Everything was so clean, which made our experience even more enjoyable. We’re grateful for your hospitality and thoughtfulness!
Superhost
Home in Highland
4.78 out of 5 average rating, 18 reviews

Classic Hudson Valley Riverfront House with Pool

GeraldineRating, 5 stars3 months ago
We had a wonderful time at Dan’s house! The peaceful surroundings made it the perfect getaway after the hectic holiday season. The house itself was clean, cozy, and thoughtfully equipped with all the amenities we could need. The fireplace and piano added such lovely, warm touches to our stay, and we especially enjoyed the stunning view of the river. With multiple rooms to spread out, everyone had their own space to relax, which made our stay even more comfortable. The kitchen was fully stocked with everything we needed, and the central location was ideal for exploring nearby towns like Kingston, Poughkeepsie, and New Paltz. On top of everything, Dan was incredibly responsive and provided clear, thoughtful instructions. He is a great host. This home was exactly what we needed to unwind, recharge, and enjoy some quality time together. We highly recommend and would love to return in the future (and enjoy the pool!).
Top Guest favourite
Home in Port Jervis
4.96 out of 5 average rating, 80 reviews

Your Summer Escape - Cozy Forest with Deck & Views

KellyRating, 5 stars3 months ago
Jairo’s Airbnb was a wonderful stay for three couples and three small dogs. His Airbnb was very spacious and had plenty of activities to do. Although we weren’t able to use the hot tub as it is only available March to November, we had a lot to do. The yard is very big and excellent for dogs to run free. It snowed the day before our stay and it rained during our stay so we couldn’t enjoy the backyard to its fullest but I would still recommended this Airbnb because it never felt crowded and had lots of activities. Communication with Jairo was excellent. He was very responsive and provided everything we needed. There were also complimentary drinks in the fridge that were very much appreciated as well. Jairo and his wife have created a beautiful and well-thought out Airbnb. We hope to be back in the warmer months to use the backyard space more.

Condo rentals with a pool

Guest favourite
Condo in Hunter
4.87 out of 5 average rating, 86 reviews

Cozy Gem with Mountain Views

VESNARating, 5 stars1 month ago
Super cozy and lovely home. Very well stocked and closed to everything. Would stay again!
Condo in Windham
4.67 out of 5 average rating, 117 reviews

Windham Condo

AlisonRating, 5 stars5 months ago
We had an amazing stay at Kristen’s condo with our family—my husband, our toddler, and our dog. The location was perfect—secluded and peaceful, but still close to hiking trails and charming small towns. The condo was cozy, clean, and well-equipped with everything we needed for a relaxing weekend. Kristen was responsive and helpful, making our stay even better. Highly recommend for a family getaway!
Guest favourite
Condo in Windham
4.88 out of 5 average rating, 191 reviews

Cozy Mountain hideaway Windham, Hunter

RandolphRating, 5 stars4 days ago
Pristine clean, cozy, one bedroom condo unit located in Windham with seasonal access to tennis courts and a pool. Walking distance to the beautiful Windham Path. Slept better than at home in the comfy bed. Went for two days of midweek remote work. Agnieszka, the host, was gracious and responsive. The host obviously put some genuine TLC into this place and it shows. Browsed for books at Briars & Brambles, an indie bookstore in Windham adjacent to Windham Pharmacy. Purchased groceries and firewood down the road at Hickory Hill Market . Ate in area at Higher Grounds and Windham Diner. Living room has a fireplace with large screen TV just above. Great for all seasons. Thanks Agnieszka!
Guest favourite
Condo in Windham
4.83 out of 5 average rating, 12 reviews

Windham-Hunter Lodge

MariaRating, 5 stars3 months ago
Cullen was an exceptional host. The space was exactly as described, with plenty of supplies. Communication was stellar. The condo had plenty of extras like clean linens and blankets, there were even additional chargers set up and toiletries if we needed. The beds are comfortable. The bathrooms very clean and updated. Parking right in front. We felt safe and comfortable. This AirBnB is 5 minutes to Windham mountain and minutes from Town. Plenty of places to eat and shop. I highly recommend this Host and property. If we ever go back, we will try to re-book with Cullen.
Condo in Windham
4.92 out of 5 average rating, 59 reviews

4 Bedroom Condo, Close to Golf Courses and Biking

DianeRating, 5 stars17 months ago
Fit our needs for attending a weekend wedding in the area. Appreciated the 3 full bathrooms. Hosts were very responsive when entry code didn’t work and in providing 2 missing items right away. Wish it was warm enough outside to enjoy the large deck but it was November. Enjoyed our stay.
Guest favourite
Condo in Windham
5 out of 5 average rating, 32 reviews

5-Star Lux Condo: Ski-In/Out, Heated Pool, Hot Tub

JayRating, 5 stars2 weeks ago
An excellent place to stay for a ski trip. Perfect location right at the base. Wonderful building with a great pool and hot tub. Excellent for a great ski vacation!
Guest favourite
Condo in Windham
5 out of 5 average rating, 5 reviews

Luxury Ski in Ski out Condo + Amenities

AaronRating, 5 stars3 months ago
We worked through a bit of calendar scheduling snafu quickly. Scott was accommodating, proactive, and responsive. The condo was in a great location, maintained well, and clean. We very much enjoyed our quick weekend getaway. Thank you!
Superhost
Condo in Windham
4.72 out of 5 average rating, 273 reviews

Cozy Condo w/ Wood Burning Fireplace

MichelleRating, 5 stars4 weeks ago
This was probably my favorite rental to date. I had to travel over a hard situation and it was the serenity that I needed at the end of the day It feels so cozy and really represents an escape away from home Jasmin and Ryan are wonderful easy to work with helpful and even helped me with recommendations close to the unit Plenty of blankets and amenities to enjoy thank you Jasmin and Ryan. I will be definitely contacting you again. The next time I come to that area.

Home rentals with a private pool

Home in Woodstock
5 out of 5 average rating, 9 reviews

Luxury Retreat in the Catskills

BetsyRating, 5 stars44 months ago
Hands down, our favorite place we've been in a long time. Beautifully decorated, perfect pool, great kitchen, super fast internet - not something you always find in the mountains - and a perfect location close to shops, to hikes, to restaurants. Great, great place. Can't wait to return.
Top Guest favourite
Home in Rhinebeck
5 out of 5 average rating, 71 reviews

Rhinebeck Country Living with a Modern Twist

YetundeRating, 5 stars3 months ago
Beto and Scott are amazing host! From the complimentary wine to ensuring that we were comfortable by checking in, I couldn't ask for more. My family and I are truly appreciative to have experienced our stay in their home during the holidays. If you're considering renting this, please do (especially in the summer). No complaints!
Guest favourite
Home in Kerhonkson
4.95 out of 5 average rating, 352 reviews

Beautiful Salt Water Pool & Fully Fenced 10 Acres

InesRating, 5 stars3 weeks ago
My sister and I really enjoyed spending the week here with our two dogs! Internet is great for remote work, and the pups got to run and play out in the fenced yard. The kitchen is also really nice, spacious and has everything you need for home cooked meals. Perfect for a quiet time away from city life!
Superhost
Farm stay in Fleischmanns
4.91 out of 5 average rating, 11 reviews

Private Catskills Retreat | Hot Tub, Sauna & Tipi

ChrisRating, 5 stars15 months ago
We had a lovely time at Healing Waters Farm. Great location close to Belleayre Mountain. The place itself has everything you need, well stocked kitchen, and lovely clean bathrooms. The property has a calming stream, large swimming hot tub and sauna which we our family enjoyed. Recommend highly for a peaceful getaway.

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