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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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Cabin in Stephentown

4.84 out of 5 average rating, 237 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.

29 Jul – 5 Aug

$364 SGD per night

Guest favourite

Apartment in Hancock

4.9 out of 5 average rating, 21 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.

19–26 Oct

$245 SGD per night

Guest favourite

Home in Ghent

4.87 out of 5 average rating, 270 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Escape to our recently renovated guest house on a 12-acre property, 15min from of Hudson. Cozy up in front of the wood burning stove as you 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.

4–11 Dec

$293 SGD per night

Guest favourite

Farm stay in West Sand Lake

4.98 out of 5 average rating, 138 reviews

Roundhill Farm - Summer Getaway with Pool!

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.

1–8 Oct

$851 SGD per night

Guest favourite

Apartment in Hancock

4.83 out of 5 average rating, 131 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.

28 May – 4 Jun

$220 SGD per night

Guest favourite

Apartment in Hancock

4.95 out of 5 average rating, 19 reviews

Upscale 2 bed/2bath Condo at a Mountain Resort!

A beautiful newly renovated two bedroom condo with A/C at Jiminy Peak Mountain Resort. This natural light filled 1130 sq. ft. condo can accommodate up to 4 people with 2 bedrooms. Two full baths, a washer and dryer as well as a full kitchen will make this your home away from home. This convenient location is just a short distance from area lakes, hiking trails, restaurants, shopping and cultural venues. Take advantage of Jiminys' pools when you're not enjoying the Mountain Adventure Park!

12–19 Oct

$439 SGD per night

Guest favourite

Home in Hudson

4.93 out of 5 average rating, 227 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

13–20 Sep

$784 SGD per night

Guest favourite

Holiday home in Hancock

5.0 out of 5 average rating, 8 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.

21–28 Nov

$206 SGD per night

Guest favourite

Townhouse in Hancock

4.83 out of 5 average rating, 64 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.

2–9 Apr

$255 SGD per night

Guest favourite

Guest house in Williamstown

4.93 out of 5 average rating, 219 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.

8–15 Sep

$256 SGD per night

Guest favourite

Bungalow in Williamstown

4.89 out of 5 average rating, 202 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.

4–11 Dec

$319 SGD per night

Guest favourite

Guest house in Lenox

4.95 out of 5 average rating, 281 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

4–11 Sep

$199 SGD per night

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Popular amenities for Hancock rentals with a pool

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Air conditioning

House rentals with a pool

Guest favourite

Home in Wilmington

4.9 out of 5 average rating, 130 reviews

4 bedroom Ski House 15 min to Mount Snow

3–10 Jun

$225 SGD per night

Guest favourite

Home in Catskill

4.93 out of 5 average rating, 164 reviews

The Grandview | Catskill, NY

16–23 Sep

$908 SGD per night

Guest favourite

Home in Wilmington

4.88 out of 5 average rating, 150 reviews

Adams Farm-"The Little Farmhouse"

2–9 Oct

$405 SGD per night

Guest favourite

Home in Wilmington

4.83 out of 5 average rating, 155 reviews

The Vermont Barn (Mount Snow)

10–17 Feb

$628 SGD per night

Guest favourite

Home in Hancock

5.0 out of 5 average rating, 24 reviews

Cozy Mountain Cabin in Cultural Berkshire

12–19 Jul

$459 SGD per night

Guest favourite

Home in New Lebanon

4.98 out of 5 average rating, 49 reviews

Berkshire Mountain retreat gorgeous views and pool

9–16 Sep

$786 SGD per night

Guest favourite

Home in Hancock

4.85 out of 5 average rating, 41 reviews

Jiminy Peak Peaceful Home in Berkshires

30 Dec – 6 Jan

$674 SGD per night

Guest favourite

Home in Cheshire

4.94 out of 5 average rating, 50 reviews

Berkshire County modern home + pool

14–21 Mar

$594 SGD per night

Apartment rentals with a pool

Guest favourite

Apartment in Dover

4.99 out of 5 average rating, 100 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

7–14 Sep

$230 SGD per night

Guest favourite

Apartment in Dover

4.99 out of 5 average rating, 105 reviews

*Mountain Oasis: Base of Mount Snow Retreat*

22–29 Sep

$488 SGD per night

Guest favourite

Apartment in Dover

4.88 out of 5 average rating, 146 reviews

Cozy condo with great views of Mt. Snow

12–19 Oct

$721 SGD per night

Guest favourite

Apartment in Dover

4.87 out of 5 average rating, 222 reviews

Mt Snow Ski In/Out at Seasons

29 Sep – 6 Oct

$295 SGD per night

Guest favourite

Apartment in Hancock

4.93 out of 5 average rating, 15 reviews

Large one bedroom, two full bath, full kitchen

4–11 Jul

$233 SGD per night

Guest favourite

Apartment in Hancock

4.93 out of 5 average rating, 58 reviews

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit1

20–27 Oct

$360 SGD per night

Guest favourite

Apartment in Hancock

4.97 out of 5 average rating, 37 reviews

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

5–12 Jan

$722 SGD per night

Guest favourite

Apartment in Hancock

4.88 out of 5 average rating, 33 reviews

Unique - Country suite @ Jiminy Peak

5–12 Mar

$495 SGD per night

Quick stats about holiday rentals with a pool in Hancock

Total rentals
120 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
70 properties are a good fit for families
Total number of reviews
1.9K reviews
Nightly prices starting at
$82 SGD before taxes and fees

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