
Holiday rentals with a pool in Woodstock
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Woodstock
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Popular amenities for Woodstock rentals with a pool
House rentals with a pool

The House on the Hill
Gorgeous house in the heart of Saugerties. The house is located on a quiet street among nature and right next to the water. It is full of old world charm and extremely spacious with a fantastic garden and a very large pool. We were two families (9 total) so we put the whole house to great use. The 5 bedrooms allowed everyone to have their own space. Multiple living rooms and a nice porch were great features The kitchen is well stocked and was put to good use! Claudia and Paul were super reactive to any questions or query. Saugerties is very close (5 min drive) and Woodstock is only a 15 min drive away. Highly recommend for families or group getaway!

MCM in the Hudson Valley
Beautiful home. Great vibes with cool art and decorations. Nearby the Fishill Farm, and the Beacon metro north. Highly recommended to stay here.

Newly Built Private Home & Pool
My wife and I and our two young kids spend four wonderful days at Amy’s house in Accord. The house is stunning and the location is perfect - on a very quiet street but near some of the best amenities in the region. We would not hesitate to return.

Columbia County Farmhouse with Pool
Beautiful house with lots of beds and spaces to hang out. We had a lovely time here visiting the Hudson Valley in the early spring. Would certainly come back!

NEW! Catskill Family Hideout with Seasonal Pool
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!!

Entire Home (private pool), Event Friendly
Faisal was extremely responsive throughout our stay. we loved the indoor pool and the game tables. there was a nice selection. The rooms were nice. It was great that the bedrooms were on the same floor as the living room, dining room and kitchen. We came with an elderly person and they were able to make their way around the house. my son asked if he can use the fire pit out in back and he was able to. he collected wood from the side of the house. nice location. we really enjoyed our stay.

Canopy Hill House - Modern w/ Pool+Hot Tub+Mt View
Amazing house that has everything you possibly need, and amazing and responsive host

Hudson Valley Oasis with in-ground pool.
Gary and Isabelle were wonderful hosts and communicated very well and were very gracious and helpful throughout our stay. Their home is very cozy and warm and comfortable, we had a wonderful time and had everything we needed there for a great stay.!! I would highly recommend their home for a stay in the Catskills if you are looking for a place there! We’ll definitely be back there in the summer as they have a wonderful large pool in the yard to enjoy !!
Condo rentals with a pool

Cozy Gem with Mountain Views
Super cozy and lovely home. Very well stocked and closed to everything. Would stay again!

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!

Cozy Mountain hideaway Windham, Hunter
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!

Hunter & Windham: Hikes, Lakes, 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.

Windham-Hunter Lodge
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.

4 Bedroom Condo, Close to Golf Courses and Biking
Nice home in a quiet area

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

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!
Quick stats about holiday rentals with a pool in Woodstock
Total rentals
30 properties
Nightly prices starting at
$170 AUD before taxes and fees
Total number of reviews
3.1K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Windham Mountain
- Bethel Woods Center for the Arts
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- Howe Caverns
- Albany Center Gallery
- The Kartrite Resort & Indoor Waterpark
- Resorts World Catskills
- Taconic State Park
- Walkway Over the Hudson State Historic Park
- Thunder Ridge Ski Area
- Zoom Flume
- John Boyd Thacher State Park
- Mohawk Mountain Ski Area
- Brotherhood, America's Oldest Winery
- Hudson Highlands State Park
- Opus 40
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Villa Roma Ski Resort
- Kent Falls State Park
- Naumkeag