Vacation rentals with a pool in Rhinebeck

Find and book unique homes with a pool on Airbnb

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Popular amenities for Rhinebeck rentals with a pool

House rentals with a pool

Top guest favorite
Home in Warwick
4.98 out of 5 average rating, 60 reviews

4 bedroom house with pool (Kids & Dog Friendly)

KerriRating, 5 stars4 days ago
Our stay was wonderful, and the host was great from beginning to end! Highly recommend
Top guest favorite
A spacious outdoor deck surrounds a circular pool, featuring a clear blue surface and a ladder for easy access. A patio umbrella stands over a seating area with two chairs and a table, set against a backdrop of lush greenery and tall trees.
Home in Catskill
5 out of 5 average rating, 19 reviews

NEW! Catskill Family Hideout with Seasonal Pool

DeborahRating, 5 stars1 month ago
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!!
Guest favorite
An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.
Home in Newburgh
4.88 out of 5 average rating, 80 reviews

Entire Home (private pool), Event Friendly

ChannyRating, 5 stars1 week ago
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.
Guest favorite
Home in New Paltz
4.93 out of 5 average rating, 133 reviews

Harrison Field 10Acres Pool FirePit BikeRailTrail

AlannaRating, 5 stars6 months ago
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!
Superhost
An in-ground pool is surrounded by a grassy area and bordered by a wooden fence. A pair of lounge chairs and an umbrella are positioned nearby, with greenery framing the backdrop of rolling hills and trees, creating a serene outdoor space.
Home in Grahamsville
4.89 out of 5 average rating, 91 reviews

Spacious Catskills Farmhouse w/ In-Ground Pool!

AnnRating, 5 stars2 months ago
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.
Guest favorite
A spacious heated pool, surrounded by a stone deck, sits within a glass-enclosed area with retractable sides. Colorful lounge chairs are positioned around the pool, inviting relaxation. A hot tub can be seen in the background, all amidst a lush landscape of trees.
Home in Saugerties
4.86 out of 5 average rating, 86 reviews

Unique Contemporary on 40 Pvt Ac, Enclosed Hot Tub

NadineRating, 5 stars2 months ago
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!
Guest favorite
Home in Preston-Potter Hollow
4.91 out of 5 average rating, 32 reviews

Catskill Home w/ Sauna, by ski &Mountain view

DavidRating, 5 stars3 months ago
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!
Superhost
Home in Highland
4.78 out of 5 average rating, 18 reviews

Classic Hudson Valley Riverfront House with Pool

GeraldineRating, 5 stars3 months ago
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

Guest favorite
A cozy living area features a light-colored sofa facing a decorative coffee table. A round rug with a nature motif complements the hardwood flooring. Large windows provide access to natural light, and a balcony can be glimpsed through the sliding glass door.
Condo in Windham
4.88 out of 5 average rating, 191 reviews

Cozy Mountain hideaway Windham, Hunter

RandolphRating, 5 stars1 week ago
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!
Guest favorite
A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.
Condo in Hancock
4.95 out of 5 average rating, 57 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

JenniferRating, 5 stars1 month ago
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!
Superhost
An outdoor swimming area features a curved pool and a hot tub, surrounded by lounge chairs. Large windows provide a view into the indoor spaces. The area is well-lit, enhancing the inviting atmosphere during the evening hours.
Condo in Hancock
5 out of 5 average rating, 5 reviews

Condo Resort at Jiminy Peak Ski Mountain's Base

MaryRating, 5 stars2 months ago
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!
Superhost
Condo in New Ashford
5 out of 5 average rating, 5 reviews

Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8

NicoleRating, 5 stars2 months ago
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!
Guest favorite
A welcoming living area features a brown leather sofa with decorative pillows, a wooden coffee table, and a comfortable armchair. Soft lighting is provided by a floor lamp and a wall-mounted lamp. A sliding glass door leads to an outdoor deck surrounded by trees.
Condo in Windham
4.83 out of 5 average rating, 12 reviews

Windham-Hunter Lodge

MariaRating, 5 stars3 months ago
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.
Guest favorite
A spacious outdoor balcony features black wooden chairs set against a backdrop of colorful autumn foliage. The heated pool and hot tubs are visible below, with the surrounding landscape showcasing a mix of greens and vibrant fall colors.
Condo in Windham
5 out of 5 average rating, 32 reviews

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

JayRating, 5 stars4 weeks ago
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!
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
4.72 out of 5 average rating, 275 reviews

Cozy Condo w/ Wood Burning Fireplace

RachelRating, 5 stars1 week ago
We loved staying here for the second time! thank you!
Guest favorite
A living area features a beige sofa with cushions, positioned beside a dark wood coffee table. Natural light enters through a large window with tan drapes, offering a view of grassy landscaping. A simple lamp stands next to the sofa, enhancing the cozy ambiance.
Condo in Hancock
4.92 out of 5 average rating, 65 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

MeganRating, 5 stars1 week ago
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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