Holiday rentals with a pool in Catskill Mountains

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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, 18 reviews

NEW! Catskill Family Hideout with Seasonal Pool

DeborahRating, 5 stars1 week 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
4.86 out of 5 average rating, 69 reviews

Entire Home (private pool), Event Friendly

ChristinaRating, 5 stars1 week ago
We had a great time for my sister in law’s bachelorette. About an hour from Warwick Winery but worked our way back to the more local ones. Had a minor issue with the hottub but Faisal offered to send someone to fix it in the moment, which def was not necessary. Would absolutely stay at this house again!
Guest favourite
Home in New Paltz
4.93 out of 5 average rating, 133 reviews

Harrison Field Upstate NY Weekend Getaway

AlannaRating, 5 stars4 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 Lanesville
4.83 out of 5 average rating, 6 reviews

New 8BR/4B home Pool, Hottub & sauna in Hunter

YaakovRating, 5 stars6 months ago
We went on a family summer vacation and we had an amazing experience! The house was clean and spacious and even nicer then the pictures listed. The pool was clean the sauna worked well. There are air condions in all the rooms and David was extremely helpful. it's a beautiful area with a lots of attractions for kids and adults close by, we hope to come back again
Superhost
Home in Grahamsville
4.89 out of 5 average rating, 91 reviews

Spacious Catskills Farmhouse on over 5 acres!

AnnRating, 5 stars3 weeks 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 stars2 weeks 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 stars1 month 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!
Guest favourite
Home in Clinton Corners
4.9 out of 5 average rating, 29 reviews

Gorgeous Hudson Valley Farmhouse pool & sauna

FrankRating, 5 stars2 months ago
Sophie was very helpful with anything we needed. She was very easy to contact. This is our second year at the house and felt like being right at home during Christmas. Lots of rooms for everyone's privacy. Also love the early check-in. and late checkout as well. We truly thank you again Sophie for having us again.

Condo rentals with a pool

Guest favourite
Condo in Hunter
4.87 out of 5 average rating, 85 reviews

Cozy Gem with Mountain Views

VESNARating, 5 stars2 days ago
Super cozy and lovely home. Very well stocked and closed to everything. Would stay again!
Condo in Windham
4.66 out of 5 average rating, 116 reviews

Windham Condo

AlisonRating, 5 stars4 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
4.89 out of 5 average rating, 183 reviews

Cozy Mountain hideaway Windham, Hunter

BreanneRating, 5 starstoday
Cozy home base for a quick trip to ski at Windham! Perfect for two adults and a dog. Loved sitting on the balcony as the sun set and we enjoyed the fireplace. Super close to the Windham Path, great restaurants nearby.
Guest favourite
Condo in Windham
4.94 out of 5 average rating, 36 reviews

Lovely stylish 2-bedroom condo with community pool

KathrynRating, 5 stars2 weeks ago
Had a great stay. Great location next to the mountain. Comfortable beds. Highly recommend for a ski weekend.
Guest favourite
Condo in East Jewett
4.97 out of 5 average rating, 29 reviews

Hunter & Windham: Hikes, Lakes, 2BR

LauraRating, 5 stars4 months ago
My friends and I really enjoyed our stay. We hiked the devils path trail and Dimitry’s place was perfectly close to the trail and the restaurants around it. His place was great to go back to with a great shower and bath, a beautiful view and very cozy place, with coffee and a coffee maker. Very clean and Dimitry was responsive the whole way through and checkin and out was very easy. Would highly recommend and would stay again.
Guest favourite
Condo in Windham
4.83 out of 5 average rating, 12 reviews

Windham-Hunter Lodge

MariaRating, 5 stars2 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 stars15 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.
Superhost
Condo in Windham
5 out of 5 average rating, 29 reviews

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

BrendanRating, 5 stars8 months ago
LOVED staying in this condo. The condo is beautiful and so much room for our group to stay in. We were two families and a grandpa (total was 5 adults, 5 children). Location was incredible. The condo was filled with all the amenities you could need during the stay. Plenty of towels and even toothbrushes if you forget yours. Will definitely stay again.

Home rentals with a private pool

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

Luxury Retreat in the Catskills

BetsyRating, 5 stars43 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 stars2 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
Villa in Coxsackie
4.99 out of 5 average rating, 87 reviews

Magnificent Hudson River Estate with Infinity Pool and Spa

DeborahRating, 5 stars3 months ago
We celebrated thanksgiving with our entire family. So cozy and well equipped. Beds were comfortable. The house was spectacular! Amazing views! So much privacy. The owner, Jean was very accommodating and went out of her way to make sure we had everything. The caretaker Kat was just the same
Superhost
Home in Bearsville
5 out of 5 average rating, 22 reviews

Magnificent Designer Home - Close To Skiing

JessicaRating, 5 stars6 months ago
Gayle's home was absolutely stunning--the photos do not do it justice, and even they're beautiful. The grounds were just...incredible. The pool area was perfect, as was the garden, which she generously let us pick fresh vegetables from. We saw animals at all times of day, which was a treat for our 5yo. It's a less than 10 min drive to Woodstock and just a few mins to the restaurants in Bearsville. The house is spacious and decor was chic and artsy. Comfortable beds, private spaces for family members + a well-equipped kitchen. We come at the end of every summer to enjoy this area and it's the first house we would return to!!
Superhost
Farm stay in Fleischmanns
4.91 out of 5 average rating, 11 reviews

Catskills Wellness Farm Stay W/ Hot Tub & Sauna

ChrisRating, 5 stars14 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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