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Vacation rentals with a pool in Lanesborough

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Lanesborough

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, 239 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.

Jun 2 – 9

G$52,719 GYD per night

Farm stay in West Sand Lake

4.98 out of 5 average rating, 139 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.

Apr 21 – 28

G$105,989 GYD per night

Home in Ghent

4.87 out of 5 average rating, 271 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.

Jan 27 – Feb 3

G$48,296 GYD per night

Condo 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.

Jun 6 – 13

G$33,622 GYD per night

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

Sep 13 – 20

G$119,897 GYD per night

Vacation 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.

Nov 30 – Dec 7

G$33,085 GYD per night

Cottage in Newfane

4.99 out of 5 average rating, 178 reviews

Cozy Vermont Antique Sugar House with Fireplace

Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.

Jan 30 – Feb 6

G$32,327 GYD per night

Guesthouse 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.

Aug 30 – Sep 6

G$45,539 GYD per night

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.

Nov 10 – 17

G$48,850 GYD per night

Apartment in Adams

4.88 out of 5 average rating, 58 reviews

Mountain Living, 1-bedroom unit, outdoor hot-tub

Relax & enjoy nature in this tranquil, 1 bedroom unit down the block from Mt. Greylock, highest mountain in MA! 2 minutes away from hiking trails, 10 minutes away from Mass Moca, 25 minutes away from Jiminy Peak ski resort. Enjoy MT Views, and jump in the outdoor jacuzzi right outside your bedroom. WiFi, AC, your own thermostat & TV. The suite you’ll be staying in is directly attached but separate access from the main house. Military and HCP discounts

Jul 28 – Aug 4

G$21,173 GYD per night

Guesthouse in Lenox

4.95 out of 5 average rating, 284 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.

Oct 25 – Nov 1

G$30,780 GYD per night

Tiny home in Ghent

4.96 out of 5 average rating, 139 reviews

Country Getaway Tiny House in woods w/Pool/Sauna

New Tiny House living space on 30 private acres with a mile of walkable trails in Beautiful Columbia County near Hudson/Chatham/Kinderhook. House has everything you need with a Queen bed, full bed, and full kitchen. The cozy space is an ideal getaway for relaxing. In the warm months enjoy the large in ground pool and renovated barn pool house. Enjoy the 6 person Sauna year round. ** Pool closed Mid-October - Mid-May, Confirm before booking.

Jul 19 – 26

G$50,450 GYD per night

Vacation rentals for every style

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Popular amenities for Lanesborough rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Wilmington

4.88 out of 5 average rating, 150 reviews

Adams Farm-"The Little Farmhouse"

Sep 29 – Oct 6

G$59,891 GYD per night

Home in Catskill

4.93 out of 5 average rating, 164 reviews

The Grandview | Catskill, NY

Jun 24 – Jul 1

G$130,252 GYD per night

Home in Wilmington

4.9 out of 5 average rating, 132 reviews

4 bedroom Ski House 15 min to Mount Snow

Sep 5 – 12

G$40,019 GYD per night

Home in Cheshire

4.94 out of 5 average rating, 50 reviews

Berkshire County modern home + pool

Feb 12 – 19

G$90,904 GYD per night

Home in Pittsfield

4.96 out of 5 average rating, 56 reviews

Berkshire Getaway Ranch 3 acres + saltwater pool

Oct 15 – 22

G$70,887 GYD per night

Home in Pittsfield

4.97 out of 5 average rating, 39 reviews

Berkshire Lakefront Home W/Pool-100%Renovated

Apr 6 – 13

G$203,478 GYD per night

Home in Dalton

4.89 out of 5 average rating, 81 reviews

Private & Stylish Berkshires House for All Seasons

Nov 17 – 24

G$90,768 GYD per night

Home in Hancock

5.0 out of 5 average rating, 24 reviews

Cozy Mountain Cabin in Cultural Berkshire

Mar 1 – 8

G$70,217 GYD per night

Condo rentals with a pool

Condo in Dover

4.99 out of 5 average rating, 100 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

Sep 15 – 22

G$35,256 GYD per night

Condo in Dover

4.99 out of 5 average rating, 105 reviews

*Summer Mountain Oasis: Base of Mount Snow Retreat

Oct 1 – 8

G$89,872 GYD per night

Condo in Dover

4.88 out of 5 average rating, 146 reviews

Cozy condo with great views of Mt. Snow

Aug 25 – Sep 1

G$110,297 GYD per night

Condo in Dover

4.87 out of 5 average rating, 222 reviews

Mt Snow Ski In/Out at Seasons

Feb 8 – 15

G$83,366 GYD per night

Condo in Hancock

4.9 out of 5 average rating, 21 reviews

All-season Berkshires ski resort condo - Sitzmark

Jul 29 – Aug 5

G$40,357 GYD per night

Condo in Hancock

4.95 out of 5 average rating, 19 reviews

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

Dec 5 – 12

G$56,086 GYD per night

Condo in Hancock

4.95 out of 5 average rating, 22 reviews

Jiminy Peak Apartment

May 21 – 28

G$34,130 GYD per night

Condo in Hancock

4.96 out of 5 average rating, 27 reviews

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2

May 11 – 18

G$43,845 GYD per night

Quick stats about vacation rentals with a pool in Lanesborough

Total rentals
120 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
1.8K reviews
Nightly prices starting at
G$12,508 GYD before taxes and fees

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