
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.

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!

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.

Le Soleil Suite - Cozy Mtn Views 10 Min To Hudson
A charming one-bedroom suite in a rural neighborhood 10 minutes by car from downtown Hudson. Your rental is a private, independent unit next to the main house. It has a full kitchen, bathroom, electric fireplace and a private backyard with a grill, firepit and pool (June to Sept.). If we are around, we give you privacy. Watch sunset over the Catskills from the living room. 1 Br with queen bed, 1 pullout sofa, 1 fold-out twin upon request. Close to Hudson, hiking, skiing, Olana and Art Omi.

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
You want to pop out of bed, walk downstairs and be right on the mountain - this is the place to be. This Stylish 1BR, 1BA suite with an additional Pull Out Queen sleeps 4 comfortably. It sits RIGHT in the Thatcher Building in front of the MAIN ski lift in Village Center. You can not get better than that! All the convenience without the bustle. This large 650 sq ft condo features brand new decor meticulously maintained, and includes a full kitchen with all the amenities. As a guest, you will

Hilltop modern with stunning mountain views
Beautiful modern residence with a pool & fireplace in Germantown. Fantastic as a weekend getaway or longer-term rental. In the front, stunning mountain views wrap around the master bedroom, kitchen, living room and deck. Out back, a spacious yard and rolling hills. Grill & eat on the big pool deck, lounge in chaises. Fully equipped kitchen, washer & dryer, and *fast wifi*. Perfect for remote work, and each space has its own desk. Shop, walk, hike, ski: Close to Hudson, Olana & Catskills.

Mid-mod VT Dream Chalet near skiing, lake & forest
Surround yourself in nature and cozy modern comfort. The romantic mid-mod-styled chalet backs to 10 acres of peaceful forest yet is just 12 min drive to Mount Snow for great skiing. 3 min. to the boat launch of gorgeous Lake Whitingham where you can rent jetskis & boats or go swimming & fishing. Hike trails to the charming town of Wilmington with its coffee shops & restaurants. Pools & hot tub up the road at clubhouse. Just steps away from iceskating, pickleball, hiking & snowmobile trails.

Hollywood Bungalow in the Berkshires #C0191633410
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.

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.

Near Saratoga – King Bed, Tub, Fire Pit & Movies
Escape to this family-friendly Clifton Park retreat—just 20 mins to Saratoga Springs and 25 to Albany. Perfect for fall getaways with a fire pit, outdoor movie screen, private playground, basketball court, and garden. Features a king bedroom, home office, full kitchen, fast Wi-Fi, soaking tub, and 20' x 55' parking for RVs or boats. Relax in the crisp autumn air, enjoy backyard movie nights, and stay productive or cozy in a quiet, peaceful neighborhood.

Modern Barn on 12 acres w Sauna, FirePit+swimming
Escape to our recently renovated guest house on a 12-acre property, 15min from Hudson. Take in the rural setting through oversized glass doors. Infared Sauna is within running distance of the swimming pond for a cold plunge. Located in a park like setting of rolling hills & colorful sugar maple trees. Fully equipped kitchen, memory foam mattress and all the amenities. In home Massage/Yoga available. XC ski from the house! 45min to downhill.

The Copake Cabin - A rustic-modern retreat.
A quiet place to get away from it all. Modern log cabin with 3 bedrooms and lots of amenities. A private heated pool, outdoor spaces, wood-burning fireplace and outdoor fire pit. For those working remotely, there is super-fast WiFi and a designated work space. Close to the best of the Hudson Valley and the Berkshires. There is a large lake nearby for boating, swimming, and kayaking in the warmer months. Skiing and sledding in the winter.

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.
Popular amenities for Hancock rentals with a pool
House rentals with a pool

Snowdrop Lodge: Beautiful Condo at Jiminy Peak

Adams Farm-"The Little Farmhouse"

Jiminy Peak Peaceful Home in Berkshires

Stunning luxury home with fire pit

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

K House: Designer Home w Fireplace Close to Skiing

Cozy Ski Cabin in Berkshires Resort

Contemporary, Warm & Cozy Home mins to Saratoga
Condo rentals with a pool

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

Mount Snow Ski Chalet

SKI IN/OUT @ Mount Snow (Hot Tub & Pool)

Mt Snow Ski In/Out at Seasons

Walk to Mt. Snow-Spa-Summer Pool

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

Cozy Mount Snow 1 Bed : Hot tub, Sauna, Deck

Ski-in/Ski-Out on Jiminy Peak
Other vacation rentals with a pool

Mountainside Condo Ski on/off

The Catamount Ski Haus with Pool & Hot Tub

Luxe Ski Getaway Base of Jiminy

LuNo - Relaxing Ski and Culture Berkshires Escape

Lake Cabin

Charming cottage w/ fireplace, privacy & skiing

Waterfront Cabin • Cedar Hot Tub & Sauna

Charming Guesthouse w/ Pool
When is the best time to visit Hancock?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ973 | ﺩ.ﺇ933 | ﺩ.ﺇ837 | ﺩ.ﺇ679 | ﺩ.ﺇ628 | ﺩ.ﺇ775 | ﺩ.ﺇ834 | ﺩ.ﺇ826 | ﺩ.ﺇ698 | ﺩ.ﺇ830 | ﺩ.ﺇ591 | ﺩ.ﺇ944 |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Quick stats about vacation rentals with a pool in Hancock

Total vacation rentals
Explore 130 vacation rentals in Hancock

Nightly prices starting at
Hancock vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

Verified guest reviews
Over 2,680 verified reviews to help you choose

Family-friendly vacation rentals
80 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
130 of Hancock vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Hancock rentals

4.9 Average rating
Hancock stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with pools Berkshire County
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- Stratton Mountain
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Catamount Mountain Ski Resort
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Zoom Flume
- Saratoga Spa State Park
- Mount Snow Ski Resort
- Norman Rockwell Museum
- Bousquet Mountain Ski Area
- Taconic State Park
- Mohawk Mountain Ski Area
- Butternut Ski Area and Tubing Center
- Mount Sugarloaf State Reservation
- Beartown State Forest
- Mount Tom State Reservation
- Opus 40
- Albany Center Gallery
- Hildene, The Lincoln Family Home
- Peebles Island State Park




