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House vacation rentals in Lanesborough

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Top-rated house rentals in Lanesborough

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Top guest favorite

The exterior of the lakefront home is displayed, featuring a two-story structure surrounded by greenery. A well-maintained lawn and rock garden enhance the inviting landscape. A shed is visible to the right, adding practical space to the property.

Home in Pittsfield

4.97 out of 5 average rating, 117 reviews

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!

Top guest favorite

A historic white house is surrounded by lush green grass and trees. The two-story structure features a covered porch on one side, with large windows reflecting the natural light. Scenic hills are visible in the background, adding to the serene countryside setting.

4.99 out of 5 average rating, 155 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.

An open living space features high wooden ceilings with exposed beams and a stylish pool table positioned at the center. A cozy couch sits nearby, with a staircase leading to a loft area visible in the background. Natural light fills the room through large windows.

4.93 out of 5 average rating, 194 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!

A bright living area features a yellow couch and two accent chairs, inviting relaxation. A patterned area rug centers the space, while natural light filters through large windows. A staircase is visible in the background, along with decorative plants and artwork adorning the walls.

Home in Pittsfield

4.95 out of 5 average rating, 173 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!

The exterior of a charming yellow house is showcased, featuring red doors and large windows. Lush greenery surrounds the entrance, with vibrant flowers in varying shades of white and purple in the foreground. An American flag is affixed to the house, adding a touch of patriotism.

4.89 out of 5 average rating, 144 reviews

The Yellow House

The Yellow House in the Berkshires is the perfect place for a getaway, just 2. 5 hours from NYC and 2 hours from Boston. This historic small town offers many activities including Jacob's Pillow, hiking trails, skiing, Mass MoCA, and The Clark Art Institute. It is close to Tanglewood in Lenox and the Norman Rockwell Museum in Stockbridge. Located steps away from The Stationery Factory, which houses a food market, gallery spaces, artisan shops, coffee shop, and the Shire Brewhouse & pub.

The historic farmhouse features a white exterior with a covered front porch and red doors. Surrounding the house is a spacious lawn with a variety of greenery, including tall trees in the background. The setting is peaceful, ideal for outdoor relaxation.

Home in Lanesborough

4.9 out of 5 average rating, 110 reviews

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.

The spacious living room features large windows that provide scenic views of the mountains and lake. A comfortable sectional sofa is complemented by a decorative throw and cushions. The ceiling is elevated with wooden beams, and stylish decor enhances the inviting atmosphere.

Home in Great Barrington

4.97 out of 5 average rating, 261 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.

Top guest favorite

The kitchen features modern appliances, including a stainless steel refrigerator and a sleek oven range. An orange barn-style door adds a pop of color, contrasting with the navy cabinetry. Cooking utensils are organized in a vibrant holder, and a soft area rug is placed on the floor.

Home in North Adams

4.99 out of 5 average rating, 107 reviews

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!

Aerial view of the property reveals a spacious house surrounded by lush greenery and rolling hills. A winding path leads to the home, and various trees provide shade in the yard. The vibrant landscape showcases a blend of rich greens under a clear sky.

Home in Lanesborough

4.96 out of 5 average rating, 101 reviews

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.

Top guest favorite

A charming two-story, red-paneled house features a welcoming front porch with white railings. Lush greenery and flowers line the stone walkway leading to the entrance, creating an inviting approach to the home.

Home in North Adams

4.98 out of 5 average rating, 424 reviews

Steps to MoCA private house + SAUNA!

Tucked away on a hilltop oasis above MoCA (3 minutes by walk) the whimsically restored house is part of a private estate. 10 min drive to Williams College & Clark. Steps to downtown & restaurants. Your stay enables us to host refugee & immigrant musicians pro bono year-round. More info on @chasehillartistretreat Note: more dates are often available beyond what the calendar shows. Please don’t hesitate to inquire!

Top guest favorite

A spacious living area features a warm wood-paneled ceiling and modern furnishings. Two sleek sofas are arranged around a wooden coffee table, while armchairs provide additional seating. Natural light floods the space through large windows framed by light curtains, enhancing the welcoming atmosphere.

Home in Cheshire

4.81 out of 5 average rating, 152 reviews

Large Secluded Berkshire Home

Rustic Berkshire Retreat Relax in this cozy home on 3.5 private acres in Cheshire with scenic mountain views. Just 5 minutes to downtown Adams and the Susan B. Anthony Birthplace, and under 25 minutes to MASS MoCA, Williams College, Mt. Greylock, and Pittsfield. Tanglewood and Jiminy Peak are within 45 minutes. Note: Sand Mill Road bridge construction in August 2024 may add about 5 minutes to travel times.

Top guest favorite

A white farmhouse-style structure is set on a lush green hill, surrounded by a clear blue sky. The building features a gabled roof, multiple windows, and a small cupola. A neat lawn frames the house, emphasizing its inviting exterior.

Home in Bennington

4.99 out of 5 average rating, 292 reviews

Cozy Modern Sugar House with spectacular views.

This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.

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Popular amenities for Lanesborough house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

An aerial view of the spacious backyard showcases a heated pool surrounded by a wooden deck. Solar panels can be seen on the roof, and lush greenery borders the property, providing a natural setting. A shed is visible in the corner, adding to the outdoor space.

Home in Lanesborough

5 out of 5 average rating, 19 reviews

Berkshire Mountain House

The outdoor pool is surrounded by a chain-link fence and features a concrete deck. Sun lounges and chairs are positioned nearby, with a colorful beach towel draped over a lounge chair. Lush greenery frames the area, providing a serene setting.

Home in Wilmington

4.87 out of 5 average rating, 171 reviews

Adams Farm-"The Little Farmhouse"

A stock tank plunge pool is surrounded by a wooden deck and gravel, featuring a pink flamingo float. A lounge chair rests nearby, inviting relaxation in the natural setting of greenery.

4.96 out of 5 average rating, 156 reviews

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

A tranquil swimming pond is framed by lush greenery and surrounded by wooden decking. Two lounge chairs are positioned on the deck, providing a relaxing spot to enjoy the natural scenery. A shaded area with wooden slats offers a cool retreat beside the water.

4.88 out of 5 average rating, 318 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Home in Saugerties

5 out of 5 average rating, 152 reviews

Upstate Modern Scandinavian Barn in the Catskills

A tranquil scene is captured at sunset, showcasing a newly renovated inground pool. The clear water reflects the golden sunlight, surrounded by lush greenery. A protective fence encloses the pool area, offering a serene view of the landscape and mountains in the background.

Home in Cheshire

4.93 out of 5 average rating, 73 reviews

Berkshire County modern home + pool

An outdoor patio area is showcased, featuring a sparkling pool surrounded by a faux stone deck. Comfortable wooden lounge chairs and a coffee table are positioned near the pool, with a hot tub visible in the background. Lush green hills stretch into the distance under a clear blue sky.

Home in Catskill

4.91 out of 5 average rating, 111 reviews

Pool*Hot Tub*Pirate Ship*Fire Pit*Luxury Farmhouse

The pool area is framed by lush greenery, featuring a large in-ground pool with a slide. A colorful inflatable float is seen in the water. A shaded patio table with chairs provides a space for relaxation, alongside a sun umbrella that casts shade over the area.

Home in Williamstown

4.89 out of 5 average rating, 218 reviews

Hollywood Bungalow in the Berkshires #C0191633410

Weekly house rentals

Top guest favorite

A hot tub is positioned outdoors on a wooden deck, surrounded by tall trees. Fresh towels are neatly arranged on a small table nearby. The serene lake, framed by lush greenery, is visible in the background, indicating a peaceful outdoor retreat.

4.96 out of 5 average rating, 54 reviews

Private Retreat: Hot Tub! Movie Room! Pool Table!

A serene view of Onota Lake is captured, showcasing vibrant autumn foliage reflected in the calm waters. Two docks are visible, with one equipped for boat access. A grassy area leads to the lake, creating a peaceful setting for relaxation.

Home in Pittsfield

4.88 out of 5 average rating, 32 reviews

Berkshire Lakehouse - 3 bedrooms - sleeps 5

A cozy seating area features an orange sofa adorned with decorative pillows in various patterns. The walls are accented with framed artwork and shelves displaying decorative items. Black curtains frame a window, allowing natural light to brighten the space.

Home in Pittsfield

4.95 out of 5 average rating, 20 reviews

Whispering Woods Guest House

Top guest favorite

The kitchen features an island with seating and woven pendant lights overhead. Modern appliances and ample cabinetry are present, with a neutral color palette and hardwood flooring. Natural light streams in through multiple windows, creating a bright and functional cooking space.

Home in Williamstown

4.97 out of 5 average rating, 35 reviews

New Berkshire home - 3 bed, 2.5 bath w/views

A snow-covered landscape is visible, with trees lining the sides of a roadway. The hills in the background are partially obscured by clouds, suggesting a serene winter atmosphere. Several homes and parked cars can be seen along the road.

Home in Hancock

4.95 out of 5 average rating, 22 reviews

Condo on the mountain

A welcoming living area is seen through an arched doorway. Two patterned chairs sit beside a small table, illuminated by soft light. A bookshelf filled with books lines the wall, while a traditional rug adds color to the wooden floor. An antique clock stands nearby.

Home in Ashfield

4.98 out of 5 average rating, 57 reviews

An 18th century farmhouse

A charming house is set on a spacious green lawn, framed by a wooden fence. Surrounding trees add to the natural landscape, with rolling hills visible in the background. The sky displays a mix of clouds, contributing to a serene atmosphere.

4.92 out of 5 average rating, 59 reviews

Mount Greylock View Retreat,3 bedroom,2 1/2 bath.

A modern glass house is situated on a gently sloping hill, surrounded by towering trees. The structure features large windows that reflect the natural surroundings, allowing light to enhance the space. Soft grass covers the hillside, leading to the home's entrance.

Home in Guilford

4.92 out of 5 average rating, 49 reviews

Vermont Mirror House

Private house rentals

A collage of spaces within the home is displayed, highlighting a comfortable living room with a stone fireplace and bookshelf, dining area, and cozy bedrooms. Outdoor seating by the pool is shown, alongside the inviting kitchen with modern appliances, capturing a blend of relaxation and comfort.

Home in Hancock

4.83 out of 5 average rating, 12 reviews

Lovely Home in the Berkshires

Top guest favorite

A modern two-story house features a combination of blue siding and natural wood accents. Large windows provide ample natural light, while a stone pathway leads to the main entrance. Lush greenery surrounds the home, complemented by landscaping that enhances its contemporary design.

Home in Hinsdale

5 out of 5 average rating, 14 reviews

Modern Lakehouse with Private Lake Access

Top guest favorite

5 out of 5 average rating, 65 reviews

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

Top guest favorite

The exterior of a historic red house is surrounded by lush green grass and trees. A stone path leads to the front entrance, while flowering plants add a touch of color to the landscape. The sky is clear with some clouds, creating a serene outdoor setting.

Home in Old Chatham

4.98 out of 5 average rating, 47 reviews

The Red House

Top guest favorite

A wooden wall sign with the words "stay awhile" is displayed above a cozy bench. The bench is adorned with a soft, white throw blanket, and two dark green pillows are positioned at the back, providing a comfortable and inviting seating area.

5 out of 5 average rating, 73 reviews

Four Season Retreat

A green grassy area is framed by a large tree on the left, with a bird feeder standing amidst a variety of plants. In the background, expansive fields and rolling hills are visible under a partly cloudy sky, suggesting a serene rural environment.

Home in Stamford

5 out of 5 average rating, 34 reviews

Comfortable Entire Farmhouse close to North Adams

Aerial view capturing a modern farmhouse cabin surrounded by vibrant autumn foliage. The landscape features a mix of lush trees in shades of orange, yellow, and green, with distant mountains visible under a clear blue sky. A dirt road borders the property.

4.91 out of 5 average rating, 35 reviews

Modern Farmhouse Retreat

Top guest favorite

A spacious living area is highlighted by large glass windows that offer views of the natural landscape outside. A wooden dining table is positioned prominently, surrounded by black chairs. A light-colored sofa features decorative pillows, while a cabinet displays items against a light wall.

Home in Saugerties

5 out of 5 average rating, 22 reviews

The Slate House | Modern Upstate Retreat w Hot Tub

Quick stats about house rentals in Lanesborough

Total rentals
50 properties
Nightly prices starting at
ﺩ.ﺇ331 before taxes and fees
Total number of reviews
2K 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

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