Holiday rentals with a pool in Hancock

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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 stars6 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!
Guest favourite
Home in Athens
4.95 out of 5 average rating, 133 reviews

Private lakefront home, hot tub & resort amenities

ParkerRating, 5 stars1 day ago
This property was fantastic. The lake is beautiful, the kayaks and canoe offered by Vincent were in great condition and easy to use to explore the lake. And the house is well decorated, comfortable, and fits a large group easily. I would highly recommend a stay. Vincent is a great communicator and made the whole process easy — zero hassle whatsoever along the way.
Superhost
Home in Nassau
5 out of 5 average rating, 3 reviews

Secluded Lux Mansion Pool Home with Amazing Views

DaifengRating, 5 stars4 months ago
Our stay at Barry and Alisha’s place was absolutely amazing! The house is spacious, beautiful, and full of character, with thoughtful details that made it truly special—especially the room with the hidden entry, which was such a fun touch. The property itself is incredible, with the biggest lot we’ve ever seen and private trails that are perfect for relaxing walks. It’s a serene escape from the hustle and bustle of city life, and we left feeling refreshed and recharged. Barry and Alisha were wonderful hosts, and their attention to detail made our stay even better. We had an unforgettable time and would highly recommend staying here to anyone looking for a peaceful retreat. Can’t wait to come back!
Top guest favourite
Home in Germantown
4.98 out of 5 average rating, 58 reviews

Columbia County Farmhouse with Pool

CarolineRating, 5 stars3 weeks ago
Beautiful house with lots of beds and spaces to hang out. We had a lovely time here visiting the Hudson Valley in the early spring. Would certainly come back!
Guest favourite
Home in Hudson
4.95 out of 5 average rating, 152 reviews

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

JuliaRating, 5 stars2 weeks ago
Our stay with Christopher was amazing! The house was so beautiful inside and was everything our group needed. The hot tub and backyard space was beautiful as well. One thing to note is that there was no washer/dryer to wash the towels in between hot tub & shower use, so bring extra!
Top guest favourite
Home in Ballston Lake
5 out of 5 average rating, 5 reviews

Perfect Upstate Gem

DevinRating, 5 stars3 days ago
Chris was an absolute spectacular host. The place itself is large and very nice. My work crew had a great stay. I could not recommend their property or them as individuals enough.
Guest favourite
Home in Hudson
5 out of 5 average rating, 11 reviews

Historic 5BR Home Minutes from Downtown Hudson

ChloeRating, 5 stars6 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!
Superhost
Home in Ghent
4.9 out of 5 average rating, 10 reviews

Farmhouse and Guesthouse w Pool, Pond and Sauna!

DavidRating, 5 stars20 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!

Apartment rentals with a pool

Guest favourite
Apartment in Hancock
4.95 out of 5 average rating, 58 reviews

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

EladRating, 5 stars1 week ago
A Perfect Stay at Elisa's! Elisa's place was absolutely magical! Located in a charming yet convenient resort, this beautifully designed space instantly felt like home. Sunlight streams through the windows, illuminating tasteful décor that balances style and comfort. What truly stands out is Elisa's hospitality. Her communication was warm and helpful, and her local recommendations led us to hidden gems throughout the area. The spotless cleanliness and private garden oasis for morning coffee or evening drinks made everything perfect. This place represents exceptional value—not just accommodation but an experience connecting you to the local community.
Superhost
Apartment 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
Apartment 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!
Apartment in Hancock
4.88 out of 5 average rating, 33 reviews

Unique - Country suite @ Jiminy Peak

BrentRating, 5 stars15 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+
Superhost
Apartment in Hancock
5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook

Ashley And NathanielRating, 5 stars14 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, 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.
Guest favourite
Apartment in Hancock
4.85 out of 5 average rating, 151 reviews

Cozy Condo @ Jiminy Peak

ElizabethRating, 5 stars2 months ago
We always book with Dawn! Her place is amazing. We feel right at home. She ensures the house has everything you could need in case you forget something. There are extra details to make your stay more comfortable. Her linens are softer than mine at home! There is plenty of space for my family of five to stay comfortably. I highly recommend booking here! We can’t wait until our next stay here.

Quick stats about holiday rentals with a pool in Hancock

  • Total rentals

    130 properties

  • Nightly prices starting at

    £45 before taxes and fees

  • Total number of reviews

    2.7K 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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