
Vacation rentals with a pool in Greene County
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Top-rated rentals with a pool in Greene County
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Popular amenities for Greene County rentals with a pool
House rentals with a pool

Perfect Family Retreat•Pool•Volleyball•Firepit
As soon as we walked into Sarah’s place, my daughter proclaimed it the “BEST HOUSE EVER!!” Everything was clean and organized, and there were so many little things that helped us feel right at home. The house is perfectly thought out for families with young kids and made our stay so convenient - from baby gates, step stools, high chairs, kids’ kitchenware, lots of toys and books, and of course - the treehouse. The house is a ~15 min drive of Saugerties, Woodstock, Tannersville, etc, which made it so convenient to get around and go out to eat. We also did hiked the Kaaterskill Falls, which was absolutely beautiful. We had a lovely, relaxing stay at Sarah’s, and my kids have been asking to go back again soon!

Catskill Family Hideout with Seasonal Pool
We loved our stay. The house was well maintained and structured. Joey communicated very well with all the details and was responsive and friendly. We were allowed a flexible check out time as well. Overall happy with the stay 🤟🏼

The Mountain House, now with Hot Tub!
Such a beautiful home, we would love to stay again. The sunroom was incredible, like being in a mid-century modern tree house! Super close to our favorite hikes, but the house was so lovely we didn't mind being stuck inside on a rainy day watching the storm roll through. Really enjoyed the hot tub, comfy beds, great linens, and nice kitchen appliances. Daniel was awesome, so helpful with our questions and went out of his way to make sure we had everything we needed for a great trip.

Lux Lakefront | Dock | Game Room | Movie Theater
If I could give 6 stars, I would! This house is super clean, great layout, and has everything needed for great stay. Check in and check out were extremely easy. Orlando was very quick to respond to all of our correspondences. He was always kind and professional when communicating with us. We stayed in the house during a snowy, chilly week in December. The house was nice and warm upon our arrival and we immediately felt right at home. The lake views are beautiful from inside the house and deck. Comfortable bed, nice furniture, and a well stocked kitchen. Airbnb photos accurately represent this lovely home. There is plenty to do in the area or you can just stay at the home and enjoy! We already booked another stay for the end of December. Thank you Orlando for sharing your home and making us feel safe and comfortable.

Hudson River Sunset Getaway
The view from this house is amazing and my family loved putting up the blinds every morning to gaze out. The sitting room and bedrooms were so lovely, homey, and comfortable to lounge in. Maura was welcoming and proactive in communication and had beautiful flowers waiting in the living room for us.

Hudson Valley Woodland Retreat with private pool.
The property is fantastic. The house itself is very large with a spacious upstairs living room with a great fireplace. Off the living room is the balcony with a great view of the mountains off in the distance and a superb Weber BBQ grill. The back of the property is also nice with a fenced in yard. The neighborhood is quiet and it is a close enough drive to either Woodstock or downtown Saugerties. There is also some great hiking in the area.

Catskill Ski Hike Lake Pet Main St Pool
This place was a rare find for a group of six of us. Upon walking and we were immediately amazed at how nice the place seems. The amenities were great, the space luxurious, and the location was phenomenal. The driving distance to grocery stores and restaurants was easy and there were quite a few stores and restaurants that were walkable as well. In terms of things to do in the area, the location was great. It was very drivable to several walking trails and all the drives were very pretty. Overall, my friends and I would absolutely love to stay here again next time we come back to the area.

Hudson River estate guest cottage
This place was an absolutely dream!! We were here celebrating with a group of friends- the space was comfortable for a group of 10, well equipped for cooking meals, and had so much charm. We didn’t want to leave and are already looking at when we can return next year. Truly the perfect upstate getaway!
Condo rentals with a pool

Cozy Gem with Mountain Views
This place was wonderful, exactly what two couples needed for a wedding we were attending at Scribner's Lodge. This was infinitely better than trying to stay at the hotel (both because of cost and comfort).

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.

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!

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!

Cozy Getaway Gem for 2 at Windham Quads.
Mariusz was a great host. The location was great, clean, cozy. Its the perfect location for a trip out of the city Will definitely be returning

Cozy Mt. Getaway/community pool!
As cozy as the description! We had a great weekend at Anne’s condo. It was the perfect location for us as we needed to be close to Scribner’s which was just across the parking lot. Beautiful view of Hunter Mountain! So many great restaurants just a few minutes away and to Kaaterskills Falls for some hiking. Anne was so great to reach out and recommend some rain friendly activities since the weather wasn’t perfect. Looking forward to staying again!
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Howe Caverns
- John Boyd Thacher State Park
- Taconic State Park
- Jiminy Peak Mountain Resort
- Albany Center Gallery
- Zoom Flume
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Catamount Mountain Ski Resort
- Windham Mountain
- Norman Rockwell Museum
- Beartown State Forest
- Hancock Shaker Village
- Opus 40
- Pineridge Cross Country Ski Area
- Naumkeag
- Hunter Mountain Resort
- Bousquet Mountain Ski Area
- Butternut Ski Area and Tubing Center
- Thaddeus Hait Farm
- Berkshire Botanical Garden
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