Holiday 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.

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Guest favourite

Apartment in Dover

4.99 out of 5 average rating, 105 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

The Handle Lodge at Snowtree Condos is a modern 1BR condo at the base area of Mount Snow. Comfortably sleeps 6 adults and is fully equipped with everything you'll need for a fun getaway with friends and family. Make a meal in the beautiful kitchen or step out on the balcony for stunning mountain views. Our modern and cozy decor, the lovely views, and proximity to the mountain make it a great place to relax and recharge. Check us out on IG for more content: @TheHandleLodge …. 18% OFF WEEKLY STAYS

Guest favourite

Home in Hudson

4.95 out of 5 average rating, 132 reviews

Hudson Retreat w/ Hot Tub, Fireplace + Fire Pit

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 favourite

Cottage in Averill Park

4.95 out of 5 average rating, 131 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, 267 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.

Guest favourite

Farm stay in West Sand Lake

4.98 out of 5 average rating, 160 reviews

Roundhill Farm - Winter Wonderland

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 30-minute drive from this airbnb! The house sleeps 11 people comfortably.

Guest favourite

Apartment in Hancock

4.85 out of 5 average rating, 142 reviews

Cozy Condo @Jiminy Peak

Nestled in the majestic Berkshire mountains, this Cozy Condo is a home away from home! It features 2 bedrooms with closets & dresser space. The master bedroom connects to a full bathroom and has a TV for when it's time to unwind in the comfort of bed! The fully equipped kitchen/dining area opens into a spacious living room. It's the perfect place for evening gatherings with friends or a romantic night in front of the fireplace! Free access to 2 heated pools, hot tubs, sauna & fitness center.

Guest favourite

Holiday home in Hancock

4.94 out of 5 average rating, 18 reviews

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

*NEW to AirBnB* 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 favourite

Townhouse in Hancock

4.85 out of 5 average rating, 72 reviews

Beautiful Jiminy Peak Townhome Family Friendly

Leave the city behind and come work remotely from our 3 bedroom, 2 bathroom newly renovated townhome. Whether you're visiting the Berkshires area in the winter for skiing at Jiminy Peak, or you're seeking summertime adventures on the lakes and the hiking trails, this 3 level home with puts you right in the middle of the action. Perfect for families, this rental is located in a community just a mile (3 minute drive) from the mountain and managed by Moresi Property Management.

Guest favourite

Guest house in Williamstown

4.93 out of 5 average rating, 238 reviews

Perfect Base for Your Berkshire Adventure

Charming private cottage with shared pool use. This newly renovated garden studio features high ceilings, a separate kitchenette with granite counters, mini fridge, microwave, queen sized bed, and rustic Arts & Crafts furniture. Located in a separate outbuilding, the cottage is close to woodland hikes, excellent biking, as well as many other attractions in the Berkshires. The beautiful in-ground pool is perfect for an afternoon dip - guest hours are usually between 3-5.

Guest favourite

Bungalow in Williamstown

4.89 out of 5 average rating, 211 reviews

Hollywood Bungalow in the Berkshires

Cool Cozy Rustic Country Bungalow with Screening Room on filmmakers/artists' enclave that's well-located in clean and beautiful Williamstown, near incredible Hiking Trails, Farms, Skiing, MASS MoCA, Clark Art Institute, Williams College, with Pool access, Cable & Smart TV, Porch and Patio, Grill, Fire Pit, Piano Bar Outbuilding with stereo & its own WIFI, First Floor Bathroom with Jacuzzi Bathtub, Laundry, fast WIFI, and lots of outlets in a quiet area on a quiet street.

Guest favourite

Home in Wilmington

4.91 out of 5 average rating, 139 reviews

Martin Ski Barn - 4BR Ski House, 15 min to Mt Snow

15 min to Mount Snow, 35 to Stratton! Come enjoy our 4 bedroom, 2 bathroom home in the charming Chimney Hill area of Wilmington, VT. This home is a perfect getaway for those looking for easy living, rest, relaxation, and family fun. The house has 4 bedrooms and comfortably sleeps 8 adults. Master bedroom has a King bed, and there is one Queen room, one Full room with a twin trundle, and one room with two Twin beds. There is also a pack n’ play available for use.

Guest favourite

Rental unit in Hancock

4.97 out of 5 average rating, 30 reviews

Ski-InSki-Out Loft Lift&MT.Views

This ski-in, ski-out loft is located right at the base of the mountain in the Thatcher Lodge in the heart of the village at Jiminy Peak. Unmatched access to all of Jiminy Peak’s year-round activities. Skiing, mountain biking, hiking, tennis, swimming, fall foliage leaf peeping, shops, restaurants and the Mountain Adventure Park including the famous Mountain Coaster, Alpine Super Slide, Euro Bungy Trampoline, Soaring Eagle, Giant Swing, and climbing wall.