
Vacation rentals with a pool in Rhinebeck
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Top-rated rentals with a pool in Rhinebeck
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Popular amenities for Rhinebeck rentals with a pool
House rentals with a pool

4 bedroom house with pool (Kids & Dog Friendly)
Our stay was wonderful, and the host was great from beginning to end! Highly recommend

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.

Harrison Field 10Acres Pool FirePit BikeRailTrail
We had a great weekend celebrating our parents anniversary. The house was plenty big for all of us and the grounds are beautiful. Nathan was quick to respond when we had trouble navigating the AC and made sure we enjoyed our stay!

Spacious Catskills Farmhouse w/ In-Ground Pool!
This is a beautiful old house with huge windows and tons of light, beautiful views, and lots of bedrooms and hang out areas so everyone has space. The kitchen had everything we needed, the beds were comfortable and the entire place was super clean and tidy. There was a good selection of games we could play and music that our family enjoyed. It was also so nice that the house was pet friendly. The only downside was that the house was quite close to the road and my kids really wanted to sled down the hill in the backyard, but there was nothing to stop them from sliding into the road. There is hardly any traffic on the road, though, so noise was not an issue. We really enjoyed our stay here! Definitely recommend for big groups or families. We are a 7 person family - teenage kids, parents, grandparents.

Unique Contemporary on 40 Pvt Ac, Enclosed Hot Tub
Such a great experience that reaffirms how hard hosts work! Robyn communicated the weather problems in advance and let us know things might be iffy getting in because of a winter storm. Instead of just making sure the home itself was pristine, relaxing, and totally picturesque, she made sure our arrival was perfect. Snow plowed, everything iced, bag of goodies hung up on our arrival. It was such incredible, flexible caretaking of the property and the guests! Besides that, onto the regular stuff- awesome kitchen, hot tub, bedrooms, everything super clean. Was a perfect winter stay!

Catskill Home w/ Sauna, by ski &Mountain view
Thank you so much for hosting us. Our family truly appreciated the easy access and the prompt responses to any questions we had. We had a wonderful time staying at the house and really enjoyed using the sauna. Everything was so clean, which made our experience even more enjoyable. We’re grateful for your hospitality and thoughtfulness!

Classic Hudson Valley Riverfront House with Pool
We had a wonderful time at Dan’s house! The peaceful surroundings made it the perfect getaway after the hectic holiday season. The house itself was clean, cozy, and thoughtfully equipped with all the amenities we could need. The fireplace and piano added such lovely, warm touches to our stay, and we especially enjoyed the stunning view of the river. With multiple rooms to spread out, everyone had their own space to relax, which made our stay even more comfortable. The kitchen was fully stocked with everything we needed, and the central location was ideal for exploring nearby towns like Kingston, Poughkeepsie, and New Paltz. On top of everything, Dan was incredibly responsive and provided clear, thoughtful instructions. He is a great host. This home was exactly what we needed to unwind, recharge, and enjoy some quality time together. We highly recommend and would love to return in the future (and enjoy the pool!).
Condo rentals with a pool

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!

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base
We had a wonderful stay at the condo - ideally located, spacious and comfortable and had everything we needed ! Definitely will be back! Elisabeth was generous, responsive and super friendly and excited for us for our trip!

Condo Resort at Jiminy Peak Ski Mountain's Base
We had a wonderful stay at Jiminy Peak.. hosts were super quick to respond with any questions. Very easy check in and check out. Will definitely be staying again in the future!

Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8
This is our second time staying and we loved it even more the second time. Christina was lovely to book with and the unit we were put in had recently been renovated so it was in great shape. You really can't beat this place for a winter family vacation. The space was clean and well appointed. I'm very finicky when it comes to hotel cleanliness, there were a few notes I'd give on the space but overall I was very happy with the space and our overall stay. The staff at Wyndham were very helpful and friendly. We will definitely return 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.

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!

Cozy Condo w/ Wood Burning Fireplace
We loved staying here for the second time! thank you!

Jiminy Peak Country Inn - ski in/out condo MT view
Very nice spot for one person or a couple. Convenient access to JP base area and amenities. Neat and tidy space, nicely appointed. Great communication from owner.
Quick stats about vacation rentals with a pool in Rhinebeck
Total rentals
20 properties
Nightly prices starting at
$130 before taxes and fees
Total number of reviews
1.1K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
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- Belleayre Mountain Ski Center
- Windham Mountain
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- The Kartrite Resort & Indoor Waterpark
- Resorts World Catskills
- Taconic State Park
- Thunder Ridge Ski Area
- Zoom Flume
- Mohawk Mountain Ski Area
- Opus 40
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Brotherhood, America's Oldest Winery
- Hudson Highlands State Park
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Beartown State Forest
- Otis Ridge
- Norman Rockwell Museum
- Naumkeag
- Thaddeus Hait Farm
- Bull's Bridge Golf Club
- Walker Road Vineyards LLC
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