
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.

The Creation Station
Welcome to The Creation Station. I am your host John. The Creation Station was built with love and care by me with my friends and family. Amenities? Update! We just installed an 8 person hot tub! Plus our pool, jacuzzi tub, projector, giant deck and a stage with sound system, drums amps and karaoke input. The most unique amenity though is The Enchanted Forest. A lit trail surrounding the property. Fun for kids of all ages! Please let me know how I can make your stay amazing. See you soon! John

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.

Modern Upstate Cabin, near Rhinebeck NY
[ 🏊🏽♂️ Heated pool is open end of May - end of October. During the winter months we recommend soaking in our giant freestanding tub, which easily fits 2 humans.] Welcome to Maitopia - our modern, dog-friendly, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub, a floating fireplace and a heated pool in the summer. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Sackett & Van Dam Guest House @ Little 9 Farm 1706
Named one of "The 10 Best Remote AirBnBs for an Escape From Reality" according to the author of 'Leave the World Behind' First Floor Open Space includes a fully equipped Kitchen (Viking Range, Dishwasher, Washer, Dryer, FridgeFreezer, Caesartone Counters), a Dining Room for 8 and a Living Room with Decorative Fireplace, Smart TV & Cable Second floor has 2 Bedrooms: One with a King bed overlooking the paddocks One with 2 Queen beds and a Desk overlooking the pool One bathroom with shower.

Berkshire family getaway at Jiminy Peak!
Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

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.

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

Hudson River Sunset Getaway
With sunset views of the Hudson River and Catskill Mountains you can relax poolside during the summer months or enjoy the changing fall colors next to a cozy back yard bonfire in the fall. Located only 5 mins to downtown Hudson where you’ll find ample dining, drinking & shopping opportunities. Or head out to explore the Catskill Mountain Range only 30 mins away for the best hiking and skiing in the area. Sunset House is the perfect place for families or a couples getaway!

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.

Enjoy every season the Berkshires have to offer.
Come enjoy the Berkshires any season you choose. We are close to local ski areas, with have access to snow shoeing, ice fishing and many more winter activities. Also located within minutes of the many cultural attractions the Berkshires have to offer, Jacob's Pillow, Shakespeare & Company, and Tanglewood. Enjoy the beautiful fall foliage on our small private pond. You can bring your kayak or canoe to enjoy the wildlife that abounds or catch & release in our pond.

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres
At the end of a dead end road on 12 acres, you'll find the perfect retreat. Highlights include a natural swimming pool, yoga deck, outdoor Japanese hot tub and sauna. Chef's kitchen, grill and smoker. Living room has a piano and seats a large group. Outside there's a 3 level stone patio, deck and firepit w/outdoor sound system. Private yoga & in-home massage. Peloton bike, Temperpedic & saatva mattress, beautiful linens! *extra 6 guests w/rental of guest house!
Popular amenities for Lanesborough rentals with a pool
House rentals with a pool

Private lakefront home, hot tub & resort amenities

Classic New England Home, Direct trail access

Adams Farm-"The Little Farmhouse"

High Field Farm

Family Lodge at Jiminy Peak - Pools & Adventure

Escape to The Berkshires w/Pool by Evergreen Home

Hudson River views with pool and hot tub

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

Winter Dream! The Handle Lodge at Snowtree Condos

Ski in-out Seasons Condo on mtn-sports center-pool

Walk to Mt. Snow-Spa-Summer Pool

Jiminy Peak Country Inn - ski in/out condo MT view
Other vacation rentals with a pool

Ski-In Ski-Out Loft Lift & MT. Views

The Nest at Birdland

Cozy Ski Retreat

Catskill Mountain View Home with Hot Tub

LuNo - Relaxing Ski and Culture Berkshires Escape

Riverfront Cabin • Heated Pool, Hot Tub & Sauna

Vermont Vacation Villa—Grapevine Getaway

All-Season Condo at Jiminy Peak (Berkshires)
When is the best time to visit Lanesborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$58,371 GYD | G$56,070 GYD | G$47,701 GYD | G$37,450 GYD | G$33,893 GYD | G$42,262 GYD | G$44,563 GYD | G$41,843 GYD | G$38,705 GYD | G$39,542 GYD | G$38,914 GYD | G$46,655 GYD |
| 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 Lanesborough

Total vacation rentals
Explore 130 vacation rentals in Lanesborough

Nightly prices starting at
Lanesborough vacation rentals start at G$14,645 GYD per night before taxes and fees

Verified guest reviews
Over 2,520 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
70 properties have a dedicated workspace

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

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

4.9 Average rating
Lanesborough stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with a fireplace Lanesborough
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- Pet-friendly rentals Lanesborough
- Rentals with a hot tub Lanesborough
- Family-friendly rentals Lanesborough
- Rentals with pools Berkshire County
- Rentals with pools Massachusetts
- Rentals with pools United States
- Stratton Mountain
- Saratoga Race Course
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Thacher State Park
- Mount Snow Ski Resort
- Butternut Ski Area and Tubing Center
- Bash Bish Falls State Park
- Bousquet Mountain Ski Area
- Zoom Flume
- Mohawk Mountain Ski Area
- Saratoga Spa State Park
- Taconic State Park
- Ski Sundown
- Norman Rockwell Museum
- Hildene, The Lincoln Family Home
- June Farms
- Naumkeag
- National Museum of Racing and Hall of Fame
- Berkshire Botanical Garden
- Hancock Shaker Village




