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House vacation rentals in Lanesborough

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Top-rated house rentals in Lanesborough

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Home in Readsboro

4.86 out of 5 average rating, 124 reviews

Relax in Peaceful Vermont! (Pet Friendly)

Beautiful Country Home, nestled in Vermont's Green mountains, panoramic views, with good access by the road. A babbling brook to lull you asleep from the master bedroom, and a clawfoot soaking tub, fully stocked house. Hiking, antiques, shops, lakes, picnics, covered bridges, cozy local inns, mountain views! Enjoy Vermont! Scenic roads, Mt. Snow, VAST trails, Mt.Greylock, Mass MOCA museum, nearby N.Adams, MA, Berkshires. Bennington Wilmington & Mt. Snow. PEACEFUL & PERFECT Vermont getaway! ☺

Home in Lee

4.9 out of 5 average rating, 252 reviews

Cozy Berkshires Cottage

Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)

Home in Pittsfield

4.97 out of 5 average rating, 105 reviews

Berkshire Pontoosuc Lake- Modern and Updated

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!

Home in Pittsfield

4.87 out of 5 average rating, 278 reviews

Dancing Horse Lodge

Dancing Horse Lodge is located in the heart of the Berkshire Mountains in Pittsfield, MA, minutes from Tanglewood, Barrington Stage, Jacobs Pillow Ballet, Kripalu Yoga, Shakespeare and Co. and skiing at Bosquet and Jiminy Peak. It is a light and bright residence located on a 20-acre horse farm with nature views out of each window. It is surrounded by miles of woods, great for hiking and cross country skiing. Close to all amenities yet affords beautiful, quiet country living. Come and enjoy!

Home in Cheshire

4.81 out of 5 average rating, 152 reviews

Large Secluded Berkshire Home

Rustic home on 3 1/2 acres in Cheshire, MA. Three Bedrooms, 2 futon couches in upstairs living space, a pull out couch in basement and 2 bathrooms (1 shower & 2 bathtubs.) Views of Mount Greylock, 5 minutes from downtown Adams and Susan B. Anthony house. Within 15 minutes of MassMoca, Williams College, Mt. Greylock, 20 minutes to Pittsfield and 35 minutes to Jiminy Peak and 40 minutes to Tanglewood. *Sand Mill Road bridge is under construction August 2024 adding 5 minutes to most trips.*

Home in Dalton

4.99 out of 5 average rating, 139 reviews

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.

Home in Dalton

4.93 out of 5 average rating, 183 reviews

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!

Home in Pittsfield

4.94 out of 5 average rating, 141 reviews

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!

Home in Williamstown

4.98 out of 5 average rating, 123 reviews

Quality, Comfort, Charm in Williamstown Center

Stay at this brand new old house in the center of Williamstown! Conveniently located in a quiet neighborhood within easy walking distance to the town center, Williams College and The Clark Art Institute. The house was fully renovated in 2021. All new everything including appliances, a luxurious tile shower, fresh sheets and towels and lovely furnishings, all to make your stay comfortable and cozy. The living room has a beautiful gas fireplace and smart tv and in the summer, central air.

Home in Chester

4.96 out of 5 average rating, 335 reviews

Riverfront Getaway

Our place is on a gentle flowing river, close to waterfalls, walks and the Berkshire cultural sites like Tanglewood and Jacobs Pillow . You’ll love our place because of the river, the deck, the hot tub; complete tranquility and a home away from home. Close to some great sites and activities, far enough away to escape. Our place is good for couples, friends and solo adventurers. Snowboarders/Skiers (or snow bunnies) and families can have great fun too! Sit back, relax and enjoy our home!

Home in Lanesborough

4.9 out of 5 average rating, 108 reviews

Elmwood Farmhouse

Renovated antique 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.

Home in Great Barrington

4.97 out of 5 average rating, 238 reviews

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

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Popular amenities for Lanesborough house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Athens

4.94 out of 5 average rating, 113 reviews

Private lakefront home, hot tub & resort amenities

Home in Colrain

4.89 out of 5 average rating, 120 reviews

The 1770 House

Home in Wilmington

4.88 out of 5 average rating, 163 reviews

Adams Farm-"The Little Farmhouse"

Home in Hudson

4.95 out of 5 average rating, 128 reviews

Hudson Retreat w/ Hot Tub, Fireplace + Fire Pit

Home in Ghent

4.88 out of 5 average rating, 299 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Home in Saugerties

4.93 out of 5 average rating, 138 reviews

Redbarn House | Pool | Fire Pit | HITS | 4 BR

Home in Wilmington

4.83 out of 5 average rating, 162 reviews

The Vermont Barn (Mount Snow)

Home in Hudson

4.93 out of 5 average rating, 242 reviews

Casa Luna Country Retreat with Pool, Hudson, NY

Weekly house rentals

Home in Lanesborough

4.98 out of 5 average rating, 64 reviews

Cozy Cottage in Berkshires: Minutes to Jiminy Peak

Home in Lanesborough

5 out of 5 average rating, 12 reviews

Berkshire Mountain House

Home in Hancock

5 out of 5 average rating, 13 reviews

Bougie B's Mountainside Getaway

Home in Lanesborough

5 out of 5 average rating, 64 reviews

Cozy farmhouse @ the gateway to Mt Greylock/Jiminy

Home in Lanesborough

5 out of 5 average rating, 45 reviews

Guest Fave, Berkshires Lake View, Large Open LR

Home in Cheshire

5 out of 5 average rating, 45 reviews

The Berkshires Hummingbird House

Home in Lanesborough

4.96 out of 5 average rating, 95 reviews

Berkshire Bliss- 6BR/Minutes from Jiminy +38 acres

Home in Lanesborough

4.94 out of 5 average rating, 34 reviews

Cozy Berkshire lake house

Private house rentals

Home in Adams

4.9 out of 5 average rating, 91 reviews

Mountain View Hideaway

Home in Pittsfield

4.94 out of 5 average rating, 17 reviews

Berkshire Lakeside Retreat

Home in Williamstown

5 out of 5 average rating, 9 reviews

Cozy Log Cottage in Berkshires on 1.6 Acres!

Home in Pittsfield

5 out of 5 average rating, 24 reviews

Marie’s Place unit 3

Home in Adams

4.89 out of 5 average rating, 9 reviews

Adams Charm

Home in Hancock

4.95 out of 5 average rating, 19 reviews

Condo on the mountain

Home in Cheshire

4.96 out of 5 average rating, 68 reviews

Berkshire County Post-and-Beam Barn!

Home in Pittsfield

4.98 out of 5 average rating, 54 reviews

Spacious 4 Br+ house in the heart of Berkshires

Quick stats about house rentals in Lanesborough

Total rentals
50 properties
Nightly prices starting at
$90 before taxes and fees
Total number of reviews
1.9K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
20 properties have a pool

Destinations to explore