
Vacation rentals with a pool in Shandaken
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Shandaken
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Shandaken rentals with a pool
House rentals with a pool

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres
Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!

Canopy Hill House - Modern w/ Pool+Hot Tub+Mt View
Canopy Hill House was a really lovely homebase for our family to explore the Catskills. We loved coming back from long days to soak in the hot tub, take in the view, and cook in the well appointed kitchen. The local recommendations that Amanda provided were really helpful, as it was our first time to the area. Our kids loved the selection of card games. The house was very comfortable and had a great aura.

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!
Our stay at Susanna’s was perfect! We have zero complaints. Had everything we needed and more! We would definitely stay there again when in the area!

4Br Mountain Brook House on 130 acres w/ trails
We were 5 girlfriends staying at this property. Each one of us loved everything about it . Perfect location !

Scenic River View Escape | New Paltz
I spent my birthday at this beautiful house and couldn’t have asked for a better experience. The place was spotless and full of natural light, with lovely views that made the stay even more special. The atmosphere was peaceful and clean, and the house had everything we needed for cooking and relaxing. I truly felt at home and appreciated all the thoughtful touches. Highly recommend for anyone looking for a cozy, well-equipped getaway!

Upstate Modern Scandinavian Barn in the Catskills
We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***

Spacious Catskills Farmhouse w/ In-Ground Pool!
Our family absolutely loved staying at Alan’s home. The house is beautiful + has so much character! The kitchen for anyone who loves to cook is your kitchen away from home!! The kitchen truly is stocked + I just loved it! The weather wasn’t great when we chose to book, but we still got to use the pool twice and it has now helped our family decide to have a private pool ourselves! So thankful for this home + can’t wait to book again!

Woodstock Romantic Mountain Studio w/ Pool
We loved this cute studio cabin at the end of a quiet lane in the woods. The host was accommodating and left a welcome basket with tea & muffins for our arrival. The whole unit was clean and well maintained with basic equipment for cooking. We enjoyed sitting on the veranda watching the wildlife. Convenient location for Woodstock for coffee and food, & Ashokan reservoir for walking and cycling. There were a few potholes on the access road to the property which deer use to drink from (☺️). We loved that the cabin was bug free and did not have any trace of bug spray! (We get very bad reactions to that stuff). Thank you for hosting & being respive. Recommend for a weekend 👍🏼
Condo rentals with a pool

Cozy Gem with Mountain Views
Loved this place. Very easy to find. The place is cute and co portable with good views from the main bedroom and living room. Very clean and tidy. Loved the stay.

Windham Condo
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!

Hunter & Windham: Hikes, Lakes, Swimming, 2BR
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.

4 Bedroom Condo, Close to Golf Courses and Biking
Very nice place with decent pricing. lots of room, clean, good communication from host.

Windham Mountain Ski In Ski Out - Pool Hot Tub Gym
We recently stayed at Andrew's condo, and it was nothing short of amazing! The location couldn't be better – right next to the slopes with easy accessibility to the mountain and the ski rental place. We were a group of two families, totaling 6 kids and 4 adults, and the condo was the perfect accommodation for our ski trip. The kids were thrilled with their bunkbed rooms, each equipped with their own TVs, providing a cozy and entertaining space for them to unwind after a day on the slopes. The condo itself was beautifully decorated, creating a warm and inviting atmosphere. There was plenty of room for all of us to relax and spend quality time together. The highlight for both kids and adults was undoubtedly the hot tub and pool. After a day of skiing, it was pure bliss to soak in the hot tub and enjoy the breathtaking views. A special shoutout to Andrew, our fantastic host! He was incredibly responsive and welcoming, ensuring that our stay was comfortable and stress-free.

Luxury Ski in Ski out Condo + Amenities
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!

Summer Retreat w/ Balcony & inground Pool
Was as advertised. Would recommend

Ski Windham Mountain ( Catskills, NY)
We had a wonderful long ski weekend and thoroughly enjoyed this property. Philip was a wonderful and communicative host and we would absolutely come for a visit again. Highly recommended!
Quick stats about vacation rentals with a pool in Shandaken
Total rentals
50 properties
Nightly prices starting at
ﺩ.ﺇ367 before taxes and fees
Total number of reviews
800 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Hunter Mountain
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Howe Caverns
- The Kartrite Resort & Indoor Waterpark
- John Boyd Thacher State Park
- Taconic State Park
- Resorts World Catskills
- Catamount Mountain Ski Resort
- Zoom Flume
- Windham Mountain
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Hudson Highlands State Park
- Brotherhood, America's Oldest Winery
- Villa Roma Ski Resort
- Hunter Mountain Resort
- Opus 40
- Thaddeus Hait Farm
- Plattekill Mountain