Vacation rentals in Lebanon Springs

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Lebanon Springs

Guests agree: these stays are highly rated for location, cleanliness, and more.

1 of 1 pages1 / 1

Top guest favorite

A serene lakefront property is viewed from the water, featuring a well-maintained lawn and inviting home. The structure is flanked by mature trees, while a small private dock extends into the lake, providing easy access to the water.

Home in Lanesborough

5.0 out of 5 average rating, 26 reviews

Lakefront Home on Ponstoosuc Lake, The Berkshires

Stunning lakefront property on 1-acre on Pontsoosuc Lake in western MA, in the heart of the Berkshires. This beautiful home features 3 bdrms & 2.5 baths. A large primary suite (king bed) sits on one side of the home, w/ two guest bdrms (king bed, queen bed) on the other end of the house. Kitchen, dining, and living room areas are spacious and open, with high ceilings & skylights. Cozy closed-in lakeside backporch opens to a small back deck. Large front side porch is set back from main road.

FamilyLocationCheck-in

Guest favorite

Cabin in East Nassau

4.97 out of 5 average rating, 106 reviews

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

FamilyLocationAccess

Guest favorite

An open living space with a high wood-beam ceiling is displayed. A large stone fireplace serves as a focal point, surrounded by comfortable seating. A kitchen island with stools offers additional space. Large windows allow natural light to fill the room, enhancing the inviting atmosphere.

Farm stay in New Lebanon

4.95 out of 5 average rating, 274 reviews

Barn Stay at Shadowbrook Farm

Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

LocationFamilyIndoor spaces

Guest favorite

A white building with a dark roof is set amidst vibrant fall foliage. Golden and orange leaves decorate the trees in the background, while a gravel path leads to the entrance. A bench is positioned in front of the building, inviting relaxation.

Farm stay in New Lebanon

4.9 out of 5 average rating, 69 reviews

1800s Carriage house in Berkshires / Hudson Valley

The carriage house was built in the 1800s on this Shaker farm. We've renovated it to provide modern convenience (minisplit HVAC, high speed wifi) and reviving original wood floors & antique furniture (from when it was an antique shop in the 1940s). This cozy spot is an ideal location for exploring the Berkshires & Hudson River Valley. 15-40min away from everything you want to do: Tanglewood concerts, plays, museums, hikes, lakes, skiing, wineries/breweries, farms, autumn leaves, historic sites.

FamilyLocationQuiet

Top guest favorite

A modern living area is present, featuring a light-colored sofa accompanied by two side tables. A decorative lamp is positioned next to the sofa, enhancing the inviting ambiance. The open floor plan reveals a view of the kitchen in the background, creating a cohesive living space.

Cottage in Pittsfield

5.0 out of 5 average rating, 15 reviews

Charming Lakeview Cottage in the Berkshires

Relax in a lakeview cottage on beautiful Onota Lake in the heart of the Berkshires. Pristine lake and mountain views from the living room. Convenient lake access with beach and boat launch just a few houses away. Cottage is completely up to date with open floor plan, stylish details and fully equipped for all getaways. Perfect for couples and small families. Spacious deck, patio and gardens offer peaceful outdoor space to unwind. Kayak and canoe. Central AC, Smart TV, WIFI, and so much more.

LocationWalkabilityHospitality

Superhost

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

4.96 out of 5 average rating, 230 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!

LocationValueAir conditioning

Guest favorite

A wrap-around porch features a small table with two colorful chairs, overlooking a serene lake framed by lush trees and greenery. The view showcases calm water, complemented by distant hills under a clear blue sky.

Home in Canaan

4.91 out of 5 average rating, 187 reviews

Berkshire Lakefront House with Amazing Views

Enjoy the culture of the Berkshires & Hudson - 15 min from Tanglewood, Norman Rockwell Museum, Shakespeare & Co, PS21, McHaydn Theatre, Mount Greylock, Jiminy Peak Resort, zipline parks, Bousquet & more. Restaurants & market within driving distance and a membership-only beach within a short walk or drive. Great lake views with wrap-around porch. The lake is family-friendly. We welcome couples, solo adventurers, and families. Sorry, no "Group Bookings" - book & pay via one account only.

LocationValueCondition

Top guest favorite

Home in Lee

4.99 out of 5 average rating, 316 reviews

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

LocationValueCondition

Top guest favorite

A kitchen features light blue cabinetry and a central island with a granite countertop. Above the island, open shelving displays decorative bowls and glassware. A dining table with wooden chairs is positioned nearby, while a cozy seating area is visible in the background.

Place to stay in New Lebanon

5.0 out of 5 average rating, 37 reviews

20 minutes to Tanglewood

This property is like nothing you've ever seen--a gem near the top of Mt. Lebanon with 75 acres of forest, streams, waterfalls, gardens, and historic ruins on a former Shaker settlement. The newly renovated Caretaker's Cottage has 2 bedrooms, kitchen, living room, and bathroom. The Taconic and Berkshire mountains stretch out before the deck and screened-in porch. Berkshire and Hudson Valley restaurants, shops, and entertainment are all nearby. Owners on site if you need them.

FamilyLocationQuiet

Top guest favorite

Home in New Lebanon

5.0 out of 5 average rating, 25 reviews

Modernized 1860s Getaway w/ Queechy Lake Passes*

Unwind in our quiet, spacious, light-filled, rural home without leaving modern conveniences behind. Located in Historic Lebanon Springs, our newly restored antique home is near both Hudson Valley restaurants and shops and the Berkshire's vast outdoor activities. We took great care to save this home's historic details while creating a fully modernized, comfortable retreat. Every room is thoughtfully curated with local antiques, artwork, and many unique touches you'll enjoy.

FamilyLocationHospitality

Top guest favorite

A covered porch featuring wooden flooring and a ceiling of natural wood. Two wooden chairs with striped cushions are positioned beside a small table. A rug adds texture, while expansive windows allow views of the outdoor greenery.

Home in New Lebanon

5.0 out of 5 average rating, 18 reviews

Mountain View Getaway

Relax with the whole family at this peaceful place to stay. Enjoy beautiful views of Pittsfield State Forest. Super close to Tanglewood, the Berkshires, Jiminy Peak, Balderdash Winery, Ramblewild, Queechy Lake, Shaker Ridge Trails, Williams College, and much more. The house is on 2 1/2 acres. It is a charming, cozy, and welcoming home with plenty of outdoor space. Families will love sitting by the fire pit and roasting marshmallows. Dogs are welcome for a small fee.

FamilyLocationNearby

Top guest favorite

A two-story home is depicted, featuring a grey wooden exterior with multiple windows. A wooden deck with stairs leads to the entrance, surrounded by green grass and vibrant yellow flowers. The clear blue sky complements the inviting structure.

Farm stay in Pittsfield

4.99 out of 5 average rating, 331 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

FamilyLocationCheck-in