
House vacation rentals in Lanesborough
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Top-rated house rentals in Lanesborough
Guests agree: these houses are highly rated for location, cleanliness, and more.

Net Zero home with rustic Berkshire charm
Be a part of the solution in our centrally located solar home that sits on a safe and quiet street just a walk, ride, or drive from downtown Pittsfield! Warm up your day on the screened-in sun porch. Warm up your toes on the heated tile floors! Enjoy custom concrete counters and wood floors in this open kitchen concept. Grill out on the rear patio while your dogs roam in the enclosed backyard. Hiking trails abound and playgrounds are just a stroll away. We are emissions free! How cool is that?!

Berkshire Lake- Modern and Updated-close to skiing
Lakefront Home for Rent. This home has been 100% remodelled! With a beautiful spot directly on Pontoosuc, the new kitchen, bathrooms, fireplace, and glass enclosed family room all benefit from the idyllic scenery. The home has 5 bedrooms and a convertible playroom with a futon for even more space. 2 bedrooms have bunk beds plus a full size bed in them. 2 bedrooms have king size beds and 1 has a queen. The master suite has an en-suite bathroom and a balcony overlooking the lake. Many upgrades!

Cleveland House - renovated Berkshires' gem.
Enjoy a retreat in a home full of history - it was a tavern/stage coach stop in the 1800's. Today we have added modern comfort while keeping the charm. We are centrally located in the Berkshires making it easy to enjoy -ski Jiminy, hike Mt. Greylock, and enjoy the culture. Or stay in and unwind. Play games on the flat 3-acre yard or try yoga surrounded by nature. Work remotely in our library. Walk down our country road and enjoy the farms. Most of all, reconnect with family/friends.

Brooksong, the perfect Berkshires getaway
Part of this bright, sprawling, five-acre property was built in 1866 as a schoolhouse. Its historic charm now includes all the updated comforts of home, in an idyllic country setting that's lovely in all seasons. Located a short drive from Jiminy Peak, Brooksong is perfect for a ski vacation and close to plenty of lakes for summer fun. With a pool table, fire pit, and play set for kids, this is the perfect place to recharge and have fun with the people you care about. Welcome to Brooksong!

Cantabile life in the Berkshires
Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

A paradise in the woods, minutes from MASS MoCA
Stay and wake up to the magic Berkshire sunlight ! Nestled on a quiet hill on the back of MassMoca, this house is only 3 minute drive from downtown. It was renovated in 2021 with brand new wood floors in the living room and master bedroom, and an updated bathroom with hot tub. This is a second home to the owners, who sometimes come to the area for work, the arts, and the outdoors. They treat every corner of the house with love and care, and want to share this serene experience with you.

1890 House
Back online after renovations. This beautiful Victorian farmhouse is situated on a 1/2 acre with great views of Mount Greylock, surrounding mountains and quaint town of Adams. The wraparound porch is perfect for relaxing. It is fully furnished and has a fully equipped kitchen. There is a wood stove in living room. Walking distance to Adams/supermarket. Short drive North Adams (MASSMoCA), Williamstown (Clark Museum) and Jiminy Peak (ski resort) which is 30 minutes drive.

Elmwood Farmhouse
Renovated farmhouse in the Berkshires, Perfect for family gatherings, or weekends away. Close to all the Berkshires has to offer from Tanglewood, to Mass MOCA, to other cultural and natural attractions.. Near Mount Greylock, and other outdoor destinations. The Bike Trail is just across the street with over 10 miles of scenic cycling. Whitney's Farm stand is a half mile North with fresh Produce and Deli . The house is spacious and welcoming with a sunny deck and porch.

North Adams Getaway-walk to MASS MoCA
BRAND NEW! Ready for guests to enjoy all the Berkshires has to offer! Whether you are visiting for work or pleasure, with family or friends this is a perfect place for you. Located in downtown North Adams you are surrounded by breath taking mountains and foliage, nestled between award winning museums, access to great food, and a short drive to ski resorts, breweries, Tanglewood, the highest peak in MA, and more. A true outdoorsman paradise. BOOK NOW!

Berkshire Bliss- 6BR/Minutes from Jiminy +38 acres
38 beautiful, private acres of Berkshire woods, cleared land, and mountain scenery. 6 comfortable bedrooms and 4.5 bathrooms. 9 Minutes from Jiminy Peak Ski Resort. 5 Mins from The Lake House cottages. Warm and cozy, modern gem. 4 Fireplaces, multiple hang out areas, napping areas, sauna, jacuzzi, outdoor fire pit, views in every direction, two fridges, high speed internet, plus a kid cave in the basement. Perfect for all four seasons.

Steps to MoCA private house + SAUNA! Near SKI
Take advantage of our off season prices! This home is tucked away at a private historical estate in central North Adams. Outdoor sauna, fire pits, gardens. Just a 5-minute walk to MASS MoCA, 10 mins by car to Williams & Clark. Important: all proceeds from your stay sponsor pro bono residencies for refugee & immigrant musicians. Nearest ⛷️ SKI resorts: Jiminy Peak, Berkshire East Mountain and many others.

Ski at 19th c. Barn in The Berkshires
<b> Mason Hill Farm </b> is a celebration of everything we love about the Berkshires. Mountain views, a rushing swimmable brook, an historic restored barn and outbuildings surrounded by lush forest and grazing sheep. Follow us @ <b> mason_hill_farm </b> For weddings & events, please contact us for information on our sister property: Hinterland Hall!
Popular amenities for Lanesborough house rentals
House rentals with a pool

Private lakefront home, hot tub & resort amenities

Adams Farm-"The Little Farmhouse"

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

Modern Barn on 12 acres w Sauna, FirePit+swimming

Family Lodge at Jiminy Peak - Pools & Adventure

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

Hollywood Bungalow in the Berkshires #C0191633410

Contemporary, Warm & Cozy Home mins to Saratoga
Weekly house rentals

Modern, Renovated Lakefront Escape

Berkshire Lakehouse - 3 bedrooms - sleeps 5

Cozy Cottage in Berkshires: Minutes to Jiminy Peak

Winter Wonderland 15 minutes to Jimmy Peak

13-Min Jiminy, Fave, Hot Tub, Lg Open LR, Family

The Berkshires Hummingbird House

Cozy Berkshire lake house

Colorful Urban Cabin Steps from Mass MoCA
Private house rentals

Cozy Ski Cabin! Hot Tub • Movie Room • Game Room

2 BR 2BA Condo Jiminy Peak Retreat w Mtn Views

Marie’s Place unit 3

Condo on the mountain

The Vermont Farmhouse+Ski Bromley+Holiday Escape!

The Red House

Berkshires Black Abbey - Ski Butternut

Spacious 4 Br+ house in the heart of Berkshires
When is the best time to visit Lanesborough?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,267 | ﺩ.ﺇ1,311 | ﺩ.ﺇ1,249 | ﺩ.ﺇ1,219 | ﺩ.ﺇ1,249 | ﺩ.ﺇ1,300 | ﺩ.ﺇ1,249 | ﺩ.ﺇ1,307 | ﺩ.ﺇ1,146 | ﺩ.ﺇ1,249 | ﺩ.ﺇ1,256 | ﺩ.ﺇ1,285 |
| 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 house rentals in Lanesborough

Total vacation rentals
Explore 60 vacation rentals in Lanesborough

Nightly prices starting at
Lanesborough vacation rentals start at ﺩ.ﺇ331 per night before taxes and fees

Verified guest reviews
Over 2,250 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
60 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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- Stratton Mountain
- Saratoga Race Course
- Six Flags New England
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Catamount Mountain Ski Resort
- Zoom Flume
- Saratoga Spa State Park
- Mount Snow Ski Resort
- Norman Rockwell Museum
- Bright Nights at Forest Park
- Taconic State Park
- Bousquet Mountain Ski Area
- Butternut Ski Area and Tubing Center
- Mohawk Mountain Ski Area
- Mount Sugarloaf State Reservation
- Beartown State Forest
- Albany Center Gallery
- Mount Tom State Reservation
- Hildene, The Lincoln Family Home




