
Holiday 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.

SKI IN/OUT @ Mount Snow (Hot Tub & Pool)
Escape to Seasons on Mount Snow & stay in our fully equipped 2 bedroom (ski in/out) condo. Our location is the best on the mountain ... right between the main face & Carinthia Freestyle Park! Enjoy the log burning fire (wood provided), smart TV & boardgames plus the fabulous Seasons on Mount Snow facilities where you can relax in a hot tub, pool or sauna. See below for info on activities in the warmer months including hiking, biking, scenic rides, lakes, golf, camp, a spa & the fall colors!

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!

Le Soleil Suite - Firepit, Mtn Views Near 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.

Walk to Mt. Snow-Spa-Summer Pool
*Exterior construction on siding until end of Feb *Amenity rich studio only a 5 min walk to Mt. Snow's famed Magic Carpet (runs on weekends) *Gas Fireplace *Queen memory foam Murphy bed *Queen pull out with memory foam mattress *Well appointed kitchen *65" curved UHD TV *25Mbps Wifi *USB wall outlets *Blue tooth music streaming to TV *Ample closet space *Patio with rocking chair *Easy 1st floor access *Fitness center access *Hot tub *Outdoor pool seasonal *Loaner amenities such as phone charger

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.

Base of M.S. All Seasons Fun. Deck/HotT/Pool/Sauna
Sunsil Loft @ MountSnow, your ideal Getaway. Walk to the Base. Unbeatable access to skiing, hiking, biking. Vermont never stops to surprise you with its outdoor adventures, great food and views. The loft offers a cozy gas fireplace, private deck. The kitchen has all you need to prep meals. You also have access to the pool (Summer), sauna, hot tub and GYM. Whether you’re skiing, hiking and biking in summer, or enjoying the fall foliage, our loft is your perfect home base in the Green Mountains.

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.

Cozy Mt Snow Ski In / Out
Directly on the mountain. Ski right back to door. Less than 2 minute walk to the trails. Full kitchen, dishwater, washer/dryer, microwave. Fireplace with free wood. Large screen TV in living room and 1 in each bedroom. Ground floor with private deck with tables and chairs for relaxing. Free parking. Condo across the hall is also available for larger groups. The pool (indoor & outdoor) and hot tubs are free to renters as is fully equipped gym (all year) and tennis courts in summer.

4BR Cabin w/ Hot Tub & Pools –15 mins to Mt Snow
Family-friendly cabin in Chimney Hill, just 15 min to Mount Snow & 35 to Stratton! Relax in our 4BR, 2BA home with a hot tub, indoor and outdoor pools, fire pit, clubhouse gym, fully equipped kitchen & cozy living spaces. Sleeps 8 comfortably (King, Queen, Full + trundle, 2 Twin Bunks) with a Pack ’n Play for little ones. Perfect for skiing, hiking, or unwinding year-round. Enjoy mountain charm, modern comfort, and easy access to trails, lakes, and Wilmington’s shops & dining.

Cozy Stay – King Bed, Soaking Tub & Fire Pit
Cozy winter reset in Clifton Park—perfectly located for easy trips to Saratoga Springs, Albany, Troy, and Schenectady. Sink into a plush king bed, unwind in the soaking tub, and end the day by the fire pit under string lights. Whether you’re here for a quiet getaway, work trip, or a longer stay, you’ll have comfort, privacy, and the space to truly relax. Outdoor movie screen: “available weather-permitting” + two 65" TV indoors for winter nights.
Popular amenities for Lanesborough rentals with a pool
House rentals with a pool

Snowdrop Lodge: Beautiful Condo at Jiminy Peak

Stunning luxury home with fire pit

Hudson River Sunset Getaway

Hilltop: Panoramic Views w/ Pool near Catamount

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

K House: Designer Home w Fireplace Close to Skiing

Cozy Ski Cabin in Berkshires Resort

Casa Luna Country Retreat with Pool, Hudson, NY
Condo rentals with a pool

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

Mount Snow Ski Chalet

Slopes N Seasons | Trailside Condo at Mount Snow

Ski On/Off 2BR w/Pool, Fireplace & Arcade

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

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

Cozy Mt Snow 1-bed w/ fireplace & mountain view

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Other holiday rentals with a pool

Haddock + Cotter - Chic Farmhouse and Barn w/ Pool

The Nest at Birdland

Beautiful Jiminy Peak Townhome Family Friendly

Cozy Ski Retreat

Spacious 2-bedroom

Jiminy Peak Ski Loft with Hot Tub

Sweet Dreams Retreat

Lake Cabin
When is the best time to visit Lanesborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $467 NZD | $448 NZD | $381 NZD | $299 NZD | $271 NZD | $338 NZD | $356 NZD | $335 NZD | $310 NZD | $316 NZD | $311 NZD | $373 NZD |
| 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 holiday rentals with a pool in Lanesborough

Total holiday rentals
Explore 130 holiday rentals in Lanesborough

Nightly prices starting at
Lanesborough holiday rentals start at $117 NZD per night before taxes and fees

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

Family-friendly holiday rentals
70 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
130 of Lanesborough holiday 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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- Rentals with a fire pit Lanesborough
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- Ski-in/ski-out rentals Lanesborough
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- Waterfront 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
- Jiminy Peak Mountain Resort
- Berkshire East 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
- Zoom Flume
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Saratoga Spa State Park
- Taconic State Park
- Norman Rockwell Museum
- Ski Sundown
- Hildene, The Lincoln Family Home
- Berkshire Botanical Garden
- Naumkeag
- National Museum of Racing and Hall of Fame
- Hancock Shaker Village
- Congress Park




