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Holiday rentals with a pool in Hancock

Find and book unique homes with a pool on Airbnb

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Popular amenities for Hancock rentals with a pool

House rentals with a pool

Guest favourite
Home in Stuyvesant
4.95 out of 5 average rating, 63 reviews

Red House on the Hudson

AntoniaRating, 5 stars5 months ago
We loved our stay! Comfortable beds. Super tidy and best of all the view! If only we were there in the summer, we would’ve used the pool. Would love to return!
Superhost
Home in Saugerties
5 out of 5 average rating, 12 reviews

The House on the Hill

NicolasRating, 5 stars9 months ago
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!
Top guest favourite
Home in Saugerties
4.98 out of 5 average rating, 160 reviews

Spacious Staycation near HITS & the Hudson

McKennaRating, 5 stars5 months ago
My group loved our stay at Alan and Cara’s place for the Sheep & Wool festival. Great space for a large group; we especially loved how comfortable the living room couches were and how there was space for everyone there to gather. The place was immaculately clean. We’d love to come back again!
Top guest favourite
Home in Germantown
4.98 out of 5 average rating, 56 reviews

Columbia County Farmhouse with Pool

NancyRating, 5 stars2 months ago
This is a blissful escape from the city! Even with the cold weather, it’s beautiful, relaxing and you have a fire place is just perfect for a movie night! My family and nephews, 4 and 5 love the open space, friendly animals and just being in nature.
Guest favourite
Home in Hudson
5 out of 5 average rating, 11 reviews

Historic 5BR Home Minutes from Downtown Hudson

ChloeRating, 5 stars5 months ago
Really nice stay in the Hudson area at a gorgeous home. Recommend having a car as Ubers are not 100% reliable (but Aaron + team also gave us the name for a driver, which was very nice). The house is really beautiful and perfect for family gatherings or a nice trip away with a larger group of friends. The house is also stocked with so many games and activities to make a rainy day inside a real treat. Would definitely stay again!
Guest favourite
Home in Hudson
4.94 out of 5 average rating, 16 reviews

Kees Cottage

ElizabethRating, 5 stars4 months ago
We loved staying in Erik's house. The house is perfect. Fantastic location, beautifully put together, everything we could possibly need. They were so nice and thoughtful. This is reflected in the house. Could not be more easy and comfortable. We would definitely come back again.
Superhost
Home in Ghent
4.9 out of 5 average rating, 10 reviews

Farmhouse and Guesthouse w Pool, Pond and Sauna!

DavidRating, 5 stars19 months ago
Donna was an amazing host and extremely responsive. The property was beautiful and exactly as described in the listing. The pool, pond, sauna’s made the entire experience feel like a special escape from the city. I highly recommend this property and can’t wait to go back!
Guest favourite
Home in Taghkanic
5 out of 5 average rating, 94 reviews

Sunbeam Lodge: Pool+Hot Tub, 50 Acres, ‘70s Oasis

JennaRating, 5 stars6 months ago
The house is even better in person! The property is very secluded and beautiful, lots of amenities! It’s not far from Hudson/hikes/all kinds of things to do. There was a grocery store within 10mi radius which was very convenient. We already miss the sunbeam lodge and will definitely be returning!

Apartment rentals with a pool

Apartment in Dover
4.77 out of 5 average rating, 13 reviews

Spacious 3BR | Deck | Pool | Washer/Dryer

GabriellaRating, 5 stars3 months ago
This place is great if you are headed to Mount Snow with a large group. It is a fair price for the large size and slightly dated place. There is plenty of space for and it has a cute log cabin style. The hot tub was on and ready to use which is awesome. It is not the most updated place, but given the price, this is definitely worth what you pay for!
Guest favourite
Apartment 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 stars4 weeks 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
Apartment in Hancock
5 out of 5 average rating, 4 reviews

Condo Resort at Jiminy Peak Ski Mountain's Base

SaraRating, 5 stars2 months ago
Thank you to Hamilton & Christelle for the great resort stay! Check in was easy at the main Club Wyndham Bentley Brook building. The front desk kindly provided us with a pack-n-play and sheets for our toddler. The condo was right next to the bunny slope lift and comfortably fit eight people. We also enjoyed the hot tub, pool, sauna, and gym in the main building during our stay. The slopes were decently groomed and we got lucky with a big snowstorm the last day which made for pristine night skiing! There is a washer/dryer right in the unit and a fully supplied kitchen. They provide dish soap, sponges, laundry/dish detergent packets, tissues, paper towels, and bath soaps, so no need to worry about packing extra. If you think of anything else I'm sure the front desk could help you out, and there is a small country store on the resort campus for sandwiches and basic groceries. The restaurant nearby, Bluebird, gets pretty booked, so I recommend making reservations well ahead of time.
Superhost
Apartment in New Ashford
5 out of 5 average rating, 5 reviews

Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8

NicoleRating, 5 stars1 month 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!
Apartment in Hancock
4.88 out of 5 average rating, 33 reviews

Unique - Country suite @ Jiminy Peak

BrentRating, 5 stars14 months ago
We had a fabulous time up at Jiminy Peak and being right on the mountain at Shana’s place made it very easy to enjoy the many things to do. Shana is a great host and her unit was perfect for our family of 5. Our younger two tried counting all of the gnomes in every room. We definitely recommend staying at Shana’s place, she is very easy to work with and quick to answer any questions. Thanks again A+
Apartment in Dover
5 out of 5 average rating, 4 reviews

Cozy Townhome by Mt Snow with Ski Home Trail

ChloeRating, 5 stars33 months ago
We had a nice long-term stay at Beth and Kyles's condo while renovating our home. The location is great for Mt. Snow activities. They are pretty hands-off hosts which was fine for us, but might be difficult for some. There is a nice stand-up desk for working from home that I utilized frequently. The condo has internet and for the most part it worked well, but it could be a bit spotty during video calls, so I'd recommend having a back-up plan if video calls are part of your time here. We definitely enjoyed being able to utilize the pool and clubhouse that the condos have access to, and overall enjoyed our stay.
Superhost
Apartment in Hancock
5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook

Ashley And NathanielRating, 5 stars13 months ago
We had a wonderful time staying at Paul’s place! We had easy access to the mountain for skiing. It was wonderful to have a ski locked to store our stuff outside of the room. In addition to the wonderful accommodation our kids loved the indoor/outdoor pool after a long day on the slopes. Highly recommend Paul and his accommodation!!!
Guest favourite
Apartment in Hancock
4.92 out of 5 average rating, 63 reviews

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

JoannaRating, 5 stars4 weeks ago
A total gem. We had a great time at Renee's place and skiing at Jiminy Peak. The apartment was perfect for our family (2 adults and 2 kids) with an amazing location right next to the ski lift and heated pool/hottub. Locker for skis/boards. The apartment was very clean and tidy and it has everything you could need: extra pillows and blankets, coffee and hot cocoa, soap and shampoo, super comfortable bed. Very easy check-in/check-out. Renee was quick to respond and flexible. We look forward to coming back!

Quick stats about holiday rentals with a pool in Hancock

  • Total rentals

    130 properties

  • Nightly prices starting at

    £47 before taxes and fees

  • Total number of reviews

    2.6K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

Destinations to explore