Vacation rentals with a pool in Hancock

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Hancock

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Hudson

4.96 out of 5 average rating, 156 reviews

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

Escape to Falls Road – a private mid-century country home nestled on the edge of 20 acres of preserved woodlands. Our home has been thoughtfully updated, featuring an array of resort quality amenities as well as a wood-burning fireplace, soaking tub, outdoor shower, projector & a 4ft deep cedar hot tub to unwind in. The yard includes a stock tank plunge pool, deck, grill, and fire pit. Located just over 2 hours from NYC/Boston and only 8 miles from Hudson center. Minutes to hiking, golf, & more!

Guest favorite

Cottage in Averill Park

4.94 out of 5 average rating, 139 reviews

Cozy cottage with pool, walking distance to lake

Cozy cottage with pool, fire-pit, and a short walk to the lake. Enjoy a relaxing stay at our home exploring the lake and local eateries, or a fun family getaway at the pool. Just a short drive to your winter fun at Jiminy Peak for skiing, or Saratoga during track Season. Minutes to the Crooked Lake House for your wedding stays. Don't forget your four legged family members, while you're snowshoeing, or swimming at the lake. With WIFI and A/C you can tele-work, while sitting pool side this summer.

Superhost

Cabin in Stephentown

4.86 out of 5 average rating, 290 reviews

Cabin in the woods w cedar Hot Tub + private pond

The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.

Superhost

Condo in Hancock

4.85 out of 5 average rating, 40 reviews

All-season Berkshires ski resort condo - Sitzmark

Stay at the Jiminy Peak mountain resort near renowned museums, music, dance and theater in the beautiful Berkshires. You'll be steps from swimming, hiking, aerial adventures and thrill rides. Meals are easy with two resort restaurants, a country store and a fully equipped kitchen. Spend your days at Tanglewood, Hancock Shaker Village, Mass MoCA and other nearby attractions. Then relax on the deck or in front of TVs in each room. Return for skiing in the winter with a fireplace for extra warmth.

Top guest favorite

Farm stay in West Sand Lake

4.98 out of 5 average rating, 168 reviews

Pool, Farmhouse, Pets Welcome at Roundhill Farm

An historic 1750 farmhouse on a quiet, beautiful 120 acre property. Huge rooms with wide plank original flooring, 6 bedrooms, large family room with fireplace, kitchen, dining room, and formal living room. The property includes a pond which you're welcome to skate on in the winter, and a horse barn and pastures. In the summer you'll have access to our in-ground pool. We welcome your pets! Come ski Jiminy Peak, only a 25-minute drive from this airbnb! The house sleeps 11 people comfortably.

Guest favorite

Cottage in Saugerties

4.99 out of 5 average rating, 137 reviews

Black Ridge Cottage: Pond, Cowboy Pool & Sauna

Kick back and relax in this calm, stylish space, with private wildlife filled pond & cowboy pool This house is great for a family, or two couples. There are lots of relaxing spaces inside and several seating areas in nature outside. Ten minutes to the towns of Woodstock and Saugerties, you will have the perfect location to enjoy the best experiences the Hudson Valley has to offer. This 4 bedroom, 3 bath house has been recently gut renovated. Enjoy the beautiful design and natural landscape.

Top guest favorite

Townhouse in Clifton Park

4.99 out of 5 average rating, 151 reviews

Townhouse w/ King Bed, Kitchen, Tub, Patio, Office

Enjoy our newly furnished and remodeled, spacious Townhouse with a private entrance and king bed! Located in a quiet and safe location in the up-and-coming town of Clifton Park (Saratoga County). 25 minutes to Saratoga National Historical Park. 10 min drive from shopping, entertainment & dining. 18 minutes to Saratoga Race Course, Saratoga Performing Arts Center, and Saratoga National Golf Club. Just a short drive to downtown Albany & surrounding Troy, Schenectady, Ballston Spa and Latham.

Superhost

Home in Hudson

4.93 out of 5 average rating, 243 reviews

Casa Luna Country Retreat with Pool, Hudson, NY

CASA LUNA Perfect peaceful upstate NY country retreat. An all year round escape. 2 hours from NYC driving or Amtrak. 15 mins to downtown Hudson with great restaurants and shopping. 20 mins to water skiing on Copake Lake and 25 mins snow skiing at Catamount, Berkshires. Private & secluded. Columbia County, New York. 4 bedrooms, 2.5 bathrooms, salt water swimming pool, koi pond, claw foot bath tub, steam room. If CASA LUNA is booked check CASA SOL https://www.airbnb.com/rooms/1627143

Guest favorite

Home in Woodstock

4.98 out of 5 average rating, 146 reviews

Woodstock Historic Artist Estate- The Museum House

The property is an estate formerly owned by renowned artist Reginald Marsh located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 2500sft house is the former Museum House that used to hold Mabel Marsh’s art collection that was later acquired by the Smithsonian Institute. It has been architect gut-renovated into a dramatic living experience surrounded by nature and water. The Pond and Carriage House are at the opposite side of the estate..

Guest favorite

Apartment in Hancock

5 out of 5 average rating, 10 reviews

Artsy loft near MassMoCA with pool and hot tubs

This ski-in/ski-out loft at Jiminy Peak offers all of the amenities you could ever possibly ask for! A spacious 1 bedroom loft that sleeps up to 4 (1 Queen Bed, 1 Pullout Couch) is stylish and comfortable. We are the new owners and we are regularly updating the furniture and decor. A full kitchen, full bathroom with tub, ski locker / equipment storage, laundry in unit, dedicated parking spot, access to 2 pools and 2 hot tubs, a sauna, skiing, mountain cart, ropes course, and more!

Guest favorite

Vacation home in Hancock

4.96 out of 5 average rating, 24 reviews

Ski in/Ski Out - Building 1 Condo at Jiminy Peak

Book today and spend your ski days only steps from the lift! Get first tracks or even night ski from this one bedroom condo in Building 1 at The Country Inn at Jiminy Peak. Private parking, kitchenette, and all of the comforts of home. Visit any season to explore this beautiful Berkshire mountain. Enjoy private, gated parking, walk to the country store to get essentials, and even rent equipment right at the mountain. A family-friendly condo with food options for all.

Guest favorite

Home in Hancock

4.94 out of 5 average rating, 32 reviews

Bougie B’s Mountainside Getaway

Escape to our updated 2-bedroom, 2-bath condo at Jiminy Peak! Perfectly situated for the ski season, you'll enjoy quick access to both the slopes and apres ski. After a day on the trails, unwind at nearby restaurants like Christianson's Tavern or Bluebird & Co, offering top notch local eats. Bougie B's features updated amenities and that perfect touch of class to make you feel special. Come experience the beauty of the mountains today—your perfect escape awaits!