
Vacation rentals with a pool in Hancock
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Top-rated rentals with a pool in Hancock
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House rentals with a pool

Red House on the Hudson
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!

The House on the Hill
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!

Spacious Staycation near HITS & the Hudson
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!

Columbia County Farmhouse with Pool
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.

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres
We stayed at Chris & Sam's listing for a quick weekend trip. They left us a kind welcome gift of a bag of good coffee & some local cider. We got quite a bit of snow & turned on the heat upon arrival, unfortunately, we heard a few concerning sounds & the heat stopped working. I only mention this because Chris was over w/in 7 mins to check on what was going on, when the initial fix didn't hold, Chris brought us more firewood & then immediately went and bought us three space heaters to ensure we stayed warm since it was late. he stayed in the snow waiting for his HVAC guy who showed up within~ 90 minutes & they replaced the motor & had the heat working. Honestly, I've never had such a responsive host when there was an issue with a stay it was incredible and so appreciated! We enjoyed our stay so much, the house is very comfortable and well stocked (esp the kitchen) & the land the house is on is gorgeous and perfect for keeping my kiddo entertained in nature! Only wish there was laundry!

Berkshire Mountain retreat gorgeous views and pool
We stayed at Kristin's house for a girl's weekend getaway. The house was perfect for our group! We loved the layout and my kids especially loved the pool table and ping pong table in the basement. Kristin was super responsive to all of my inquiries and she provided some very useful tips for local recommendations. The view from the deck was stunning and it was one of the main reasons that we selected this house, especially during the Fall so that we could enjoy the foliage. It's a great house for a large group. I loved that there was no clutter throughout the house. It was very well stocked with all of the basic essentials that you need. We felt very at home during our stay and I would highly recommend it to others.

Farmhouse and Guesthouse w Pool, Pond and Sauna!
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!

10 Acre Country Estate with Pool, Hot Tub & Views!
Fantastic experience and stay. Justin was responsive and communicative as needed. Instructions were clear. House is exactly as described and very spacious. Excellent common spaces with THREE living rooms: this is super important for the adults and kids to have their own space. They were roomy and comfortable. TVs in good working order and hooked up to whatever you want to watch. Moreover, the bathrooms and kitchen were spotless. Everything worked. Adequate and more than sufficient lighting (for brightness or for ambiance). We never used the hot tub but it looks clean and maintained. Area is close to several ski resorts but 20-30 minutes from being busy.
Condo rentals with a pool

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base
Such a treat to stay right on the mountain! We loved Jiminy Peak so much and even better than a regular ski in/ski out is that you have the lodge and stores right below you, so you have the convenience of a hotel, but the privacy of a condo. You can buy food in the lodge and bring it to the condo to eat and avoid the crowds. It was really nice to watch the mountain go to sleep at night from the living room, and we even saw dear on the mountain in the morning. The electric fireplace was cozy as well. Elisa was very responsive with any questions we had. highly recommend!

Condo Resort at Jiminy Peak Ski Mountain's Base
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.

Seasons on Mt Snow Condo - Ski-In/Out
Everything was just as described. The additional amenities (pool, etc) were easily accessible. Julia was super informative and responsive. Her instructions/jnformation were spot on, so we knew exactly what to expect. Would definitely return!

Mt Snow Ski In/Out at Seasons
Andrew’s description and check in instructions were extremely detailed. Host was very easy to contact/communicate with and very accommodating. Clear instructions for check in/out, how to get to unit and how to ski in ski out. Unit description and photos are accurate. I would consider staying here in the future again.

Ski in/out - 2BR Condo - Indoor Pool/Spa
Great condo at Mt Snow. Very clean and organized. Location is on the mountain. It requires some steep walking for ski in/ski out so keep in mind for younger kids while also carrying their gear. My kids are older so it wasn’t an issue for us but worth mentioning. Eric is the perfect host - always reachable and responsive. Super accommodating when he’s able to be. We got unlucky wind hold weather and he offered to extend our check out if we wanted to ski an extra day to make up for it. Truly awesome. Can’t go wrong.

Ski in Ski out condo great location
Our stay at Christine's place was great! The condo was very comfortable and convenient to accessing the slopes. We were able to get our gear on and get to the lift so easily right from the condo! The sports complex was an added bonus with being able to use the hot tub after a long day of skiing. The kids loved the pool and given my son loves basketball, seeing the basketball game inside was super fun for him. Christine was a great host communicating details and got back right away with any question I had. We had a blast staying here and can't wait for our next visit!

Jiminy Peak Country Inn - ski in/out condo MT view
Staying at Renee’s was great ! We loved our time here, it’s really close to the ski lifts and food. You get a beautiful mountain view of seeing skiers flying down the hills and if you’re not a skier they have hiking paths which are fun as well !

Cozy Condo @ Jiminy Peak
We love the cozy cabin! This was our third time back and it just gets better each time! The cabin is perfect for our family of five. We love the fireplace and full, well-stocked kitchen. While the rest of the family skied, I took advantage of the nearby Elle Day Spa. Dawn is super responsive and gives great local suggestions. We can’t wait for our next trip.
Quick stats about vacation rentals with a pool in Hancock
Total rentals
130 properties
Nightly prices starting at
$60 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
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