Vacation rentals with a pool in Shandaken

Find and book unique homes with a pool on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Shandaken rentals with a pool

House rentals with a pool

Guest favorite
A stock tank plunge pool is surrounded by a wooden deck and gravel, featuring a pink flamingo float. A lounge chair rests nearby, inviting relaxation in the natural setting of greenery.
Home in Hudson
4.96 out of 5 average rating, 156 reviews

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

ChristopherRating, 5 stars4 weeks ago
Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!
Guest favorite
The exterior of the house showcases a modern design framed by lush greenery. A spacious deck surrounds the heated saltwater pool, equipped with lounge chairs and an umbrella for shade. The contrasting white walls and dark roof enhance the inviting atmosphere.
Home in Roxbury
4.94 out of 5 average rating, 71 reviews

Canopy Hill House - Modern w/ Pool+Hot Tub+Mt View

KatieRating, 5 stars5 days ago
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.
Guest favorite
A private saltwater pool is surrounded by lush greenery, featuring a smooth stone deck. The clear blue water invites relaxation, while steps lead into the pool. Trees provide natural shade along the perimeter, creating a serene outdoor setting.
Home in Woodstock
4.87 out of 5 average rating, 135 reviews

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!

KimberlyRating, 5 stars2 weeks ago
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!
Guest favorite
A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.
Home in Rhinebeck
4.89 out of 5 average rating, 145 reviews

4Br Mountain Brook House on 130 acres w/ trails

eveRating, 5 stars2 weeks ago
We were 5 girlfriends staying at this property. Each one of us loved everything about it . Perfect location !
Superhost
An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.
Home in New Paltz
4.86 out of 5 average rating, 159 reviews

Scenic River View Escape | New Paltz

TatiaRating, 5 stars3 weeks ago
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!
Guest favorite
Home in Saugerties
5 out of 5 average rating, 152 reviews

Upstate Modern Scandinavian Barn in the Catskills

Zoe StarRating, 5 stars4 weeks ago
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.***
Guest favorite
An in-ground pool is situated amidst a lush green landscape, surrounded by tall grass and shrubs. The house, a charming two-story structure, is visible in the background, framed by gentle hills under a pastel sky. Outdoor seating and umbrellas are arranged nearby.
Home in Grahamsville
4.9 out of 5 average rating, 96 reviews

Spacious Catskills Farmhouse w/ In-Ground Pool!

Simmandi FeRating, 5 stars1 week ago
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!
Guest favorite
A scenic aerial view showcases an outdoor pool surrounded by greenery, with mountain vistas in the background. Lounge chairs line the poolside, inviting relaxation. The property features a blend of manicured gardens and natural landscaping, creating a peaceful environment.
Home in Woodstock
4.91 out of 5 average rating, 201 reviews

Woodstock Romantic Mountain Studio w/ Pool

JannineRating, 5 stars8 months ago
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

Guest favorite
An outdoor swimming pool is surrounded by a chain-link fence, featuring clear blue water and several white lounge chairs positioned beside the pool. Lush green grass and trees frame the area, with a view of a red building in the background.
Condo in Hunter
4.87 out of 5 average rating, 87 reviews

Cozy Gem with Mountain Views

AbishekRating, 5 stars4 weeks ago
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.
An outdoor swimming pool is surrounded by a secure fence and shaded by tall trees. Several lounge chairs are positioned around the pool area, and blue umbrellas provide shade. Clear blue water reflects the sky above, inviting relaxation.
Condo in Windham
4.67 out of 5 average rating, 117 reviews

Windham Condo

AlisonRating, 5 stars8 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!
A welcoming living area features large glass doors offering views of the outdoors, with natural light enhancing the space. A comfortable seating arrangement includes a dark blue chair and a sectional sofa, while a stylish large area rug adds warmth. Decorative elements include wall art and a blooming floral arrangement.
Condo in East Jewett
4.97 out of 5 average rating, 29 reviews

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

LauraRating, 5 stars8 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.
An indoor pool area is showcased, featuring a large swimming pool with clear blue water. Sunlight filters through multiple windows, illuminating the space. Wooden beams and a high ceiling create a spacious atmosphere, complemented by seating options along the poolside.
Condo in Windham
4.92 out of 5 average rating, 61 reviews

4 Bedroom Condo, Close to Golf Courses and Biking

BrianRating, 5 stars1 month ago
Very nice place with decent pricing. lots of room, clean, good communication from host.
A spacious living area is highlighted by large windows that provide views of the surrounding landscape. A modern fireplace is set against a stone feature wall, while comfortable seating options include a sectional sofa and accent chairs. A flat-screen TV is mounted above a stylish entertainment unit.
Condo in Windham
5 out of 5 average rating, 3 reviews

Windham Mountain Ski In Ski Out - Pool Hot Tub Gym

SamanthaRating, 5 stars16 months ago
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.
Guest favorite
An aerial view captures the Whisper Creek condo set against a snowy mountain backdrop, with ski slopes winding down the hillside. The landscape features a mix of pine trees and winter terrain, while the luxury building connects to the scenic outdoors.
Condo in Windham
5 out of 5 average rating, 5 reviews

Luxury Ski in Ski out Condo + Amenities

AaronRating, 5 stars5 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
The exterior of a two-story, wooden condo is visible, featuring a warm brown facade. A covered entrance with an American flag hangs beside the stairs leads up to the unit. Lush greenery and decorative shrubs enhance the inviting surroundings.
Condo in Windham
4.73 out of 5 average rating, 280 reviews

Summer Retreat w/ Balcony & inground Pool

AndrewRating, 5 stars1 month ago
Was as advertised. Would recommend
A spacious sectional couch, upholstered in dark fabric, is arranged around a glass coffee table. The wall is decorated with three art pieces featuring deer antler silhouettes. Light cream curtains frame a window, and a lamp provides additional lighting in the cozy seating area.
Condo in Windham
4.8 out of 5 average rating, 15 reviews

Ski Windham Mountain ( Catskills, NY)

RichardRating, 5 stars41 months ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Ulster County
  5. Shandaken
  6. Rentals with pools