Holiday rentals with a pool in Woodstock

Find and book unique homes with a pool on Airbnb

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Popular amenities for Woodstock rentals with a pool

House rentals with a pool

Guest favourite
Home in Stormville
4.94 out of 5 average rating, 182 reviews

Private Hudson Valley Country Retreat

JackieRating, 5 stars2 weeks ago
This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!
Guest favourite
Home in Hudson
4.96 out of 5 average rating, 156 reviews

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

ChristopherRating, 5 stars3 weeks ago
Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!
Guest favourite
Home in Rhinebeck
4.89 out of 5 average rating, 144 reviews

4Br Mountain Brook House on 130 acres w/ trails

AnnetteRating, 5 stars2 weeks ago
It was a fantastic house with a beautiful view. Plenty of space and we really enjoyed our stay. The property itself is absolutely gorgeous. Would definitely come back.
Guest favourite
Home in Ghent
4.88 out of 5 average rating, 318 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

JasonRating, 5 stars3 weeks ago
Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.
Top Guest favourite
Home in Stamford
4.98 out of 5 average rating, 114 reviews

Hawk View

ZacharyRating, 5 stars3 weeks ago
The house is really gorgeous. Everything was very new/modern, clean, and comfortable. We enjoyed cooking meals in the kitchen overlooking the stunning view out the back. The hot tub and fire put were nice amenities to enjoy. The BBQ seemed to not be working, but other than that, no complaints. Location wise, the property is located in the northwest Catskills, near Stamford, NY, and convenient to many hiking spots in the area as well as nearby towns. The property itself its up on a hill, in what felt like a secluded and private spot, which made it feel like a real getaway and retreat. In sum, recommend this Airbnb for the nice amenities, modern touches, and amazing view.
Guest favourite
Home in Saugerties
4.95 out of 5 average rating, 108 reviews

MODERN FARMHOUSE in the WOODS

BenjaminRating, 5 stars8 months ago
We had a terrific stay. The house was exactly as advertised.
Guest favourite
Home in Bearsville
4.86 out of 5 average rating, 49 reviews

Spacious Private Retreat w. Pool + Fireplace

JacquelineRating, 5 stars3 weeks ago
A spacious home, true to the listing photos, great natural light, great location, easy drive to Woodstock restaurants & shops and hikes. Meghan was responsive, friendly, and provided great local recommendations. Note, when we stayed there were no window treatments on any of the windows in the house, including the bedrooms.
Top Guest favourite
Home in High Falls
4.98 out of 5 average rating, 102 reviews

Cozy & Spacious Country Home - All Seasons

AshleyRating, 5 stars2 weeks ago
This house absolutely reminded me of home and my childhood ! So lovely and clean. Absolutely love the heated pool ! This was the perfect house for our wedding at the Mohonk mountain house . Close and such a comfortable stay . We really enjoyed the outdoor porch sitting room . Thank you for a comfortable and wonderful stay .

Condo rentals with a pool

Guest favourite
Condo in Hunter
4.87 out of 5 average rating, 87 reviews

Cozy Gem with Mountain Views

AbishekRating, 5 stars3 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.
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!
Guest favourite
Condo in Windham
4.89 out of 5 average rating, 194 reviews

Cozy Hideaway Windham, Hunter ,Pool,Pickleball.

JessicaRating, 5 starstoday
I couldn't believe how responsive Agnieszka was! She made every effort to make sure my husband and I had a great stay. Her comfy deck, cozy fireplace, and nice shower were a godsend after my husband and I decided to brave a rainy hike. I think the place is very reasonably priced considering access to a pool and laundry are included. It's just down the street from hikes and resturants. I also enjoyed taking classes at Mountain Breeze Yoga just down the road.
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.
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.
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 favourite
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
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

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

Destinations to explore

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