Vacation rentals in Lanesborough

4.88 out of 5 average rating, 184 reviews

Apartment in Petersburgh

The Beer Diviner Brewery Apartment

The apartment is entire upstairs of back of our farm brewery & taproom. Space is 14 x 28 feet and includes living/dining/work space, bathroom has small claw foot tub with shower. Queen-sized memory foam bed; twin day bed with pull out twin mattress. High def TV, wifi, private deck, kitchenette has mini fridge, microwave, toaster oven, hot kettle for tea and and k-cup coffeemaker. Complimentary pint of craft beer in taproom. Located in a private setting in a hollow in the Taconic Mountains.

4.93 out of 5 average rating, 244 reviews

Cottage in Lanesborough

Stone School Cottage

Romantic getaway or family vacation. Charming stone building served as a one-room schoolhouse from 1832 until 1950. Beautifully situated amidst horse farms on the scenic road to Mt Greylock, centrally located midway between Williamstown and Lenox. We host lots of writers and musicians who love the bright airy space, families that have fun in this big playhouse, and couples seeking a memorable and private retreat. PLEASE NOTE: this truly-unique building has an unusual layout, described below.

4.89 out of 5 average rating, 188 reviews

Cottage in Williamstown

Cute Cozy Comfy Cottage in the Berkshires

A cute cozy cottage sleeps 4 comfortably. One queensize bed and 1 pull out couch.. Dog friendly for up to 2 dogs .More than one dog will have to be an additional fee of 50.00 each pet. My cottage sits on 13 privately owned acres. Partially fenced in.3 miles down the road from Jiminy Peak ski resort & summer activities and a short drive to Ramblewild adventure park. Hiking, boating, museums, shopping, restaurants- all sorts of activities in the Berkshires. Two minute ride to Bloom Meadows!

4.98 out of 5 average rating, 213 reviews

Cabin in Cummington

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

Apartment in Lanesborough

4.89 out of 5 average rating, 126 reviews

Cozy Rustic Apt. in 18th c. Berkshire Farmhouse

This cozy rustic studio is located at the base of Mount Greylock and a 6 minute drive from Jiminy Peak ski resort. Built in the 1700’s, this centuries old farmhouse has since been converted into four separate cute suites. Newly updated kitchen, bathroom and furniture. Enjoy exploring the sprawling 19 acre property you will be staying on which includes seasonal flower fields, thousands of berry bushes, fruit trees, creek, and walking trails full of wildlife. Follow us on IG @SecondDropFarm

4.89 out of 5 average rating, 164 reviews

Cabin in Cheshire

Private Paradise in the Berkshires

Your own private and romantic getaway behind a small orchard. A sweet running brook and outdoor shower! A short drive to all Berkshire cultural events -- Tanglewood, Jacob's Pillow, theatre festivals and more. Great dining nearby. Perfect for 2! Under COVID-19 regulations in Massachusetts, I am required to allow at least 24 hours between guests. It's a drag, but it is intended to keep us all healthy! Please forgive any inconveniences this might create in your trip plans.

4.9 out of 5 average rating, 110 reviews

Home in Lanesborough

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.

4.84 out of 5 average rating, 279 reviews

Cottage in Lanesborough

Wildlife Lakeside Cottage; views/wildlife

Fully furnished and remodeled with new upgrades in Spring 2025 including a cathedral master bedroom suite with a full bath. Our private cottage is set on a peninsula at a cove where a trout stream enters the lake. Incredible amount of wildlife, especially all types of birds. The home has sunny views everywhere. Seasonal weeds do grow in the adjacent lake which can impact water activities, especially in the summer months. Sleeps 6. Ther are two full and one 1/2 baths.

4.96 out of 5 average rating, 101 reviews

Home in Lanesborough

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.

4.93 out of 5 average rating, 145 reviews

Cottage in Lanesborough

The Sail Loft

Cozy, private house from 1850, located in the heart of the Berkshires. On a quiet street across from a pond, the cottage has access to the Ashuwillticook rail trail. Relax on the private back porch, or in the large bath tub. Sleep in late in the king sized bed, and then enjoy what the Berkshires has to offer. Close to several downhill and cross country ski spots, hiking trails and Tanglewood!

4.9 out of 5 average rating, 126 reviews

Yurt in Stephentown

Off Grid Yurt Right By The Best of The Berkshires

This is an off grid yurt with a woodstove for heat and an off grid kitchen - no running water or electricity - water can be heated on the woodstove. You'll have a comfy bed and futon. We love it when it rains. Staying inside, listening to the rain on the yurt and playing games is a highlight of our trips there. Cooking outside and enjoying a campfire & toasting marshmallows is also fun!

4.85 out of 5 average rating, 214 reviews

Home in Cheshire

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!

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Popular amenities for Lanesborough vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Lanesborough

4.96 out of 5 average rating, 78 reviews

Guesthouse in Pittsfield

The Nest at Birdland

MichelleRating, 5 stars5 days ago

The Nest was a great spot for us to rest and recoup before our NEYC day! Mary was easy to work with, communicated well, and provided a great space with so many thoughtful extras!

5 out of 5 average rating, 19 reviews

Home in Lanesborough

Berkshire Mountain House

ScottRating, 5 stars6 days ago

This property was fantastic. It was great for adults and kids. The inground pool and hot tub were used all day and night. The house had many amenities for everyone. We have 3 grand children, (ages 5-7), the hosts had all kind of spaces and toys for them to utilize. Excellent place for kids inside and out! House was very well appointed and very user friendly. We loved our family time there and would not hesitate to return. Thank you!!!

5 out of 5 average rating, 45 reviews

Cabin in East Nassau

Luxury Cabin | Breathtaking Views & Outdoor Fun

ElaineRating, 5 stars2 weeks ago

Matt and Sarah’s place is wonderful. A great place to relax and enjoy the beautiful surroundings. The house is just as described and the hosts make you feel right at home. We hope to come back again!

5 out of 5 average rating, 52 reviews

Home in Cheshire

The Berkshires Hummingbird House

LisaRating, 5 stars2 weeks ago

Karen’s place was great. Clean, nicely decorated, kitchen had all the supplies for cooking. We appreciated the extra blankets and even the white noise machine in the bedroom. Beautiful view of the lake.

Guesthouse in Williamstown

4.97 out of 5 average rating, 61 reviews

Walk to Williams * Steam Sauna * Ritz-Carlton Bed

JohnRating, 5 stars4 weeks ago

We had a great night hear. It is a wonderful town. We were at an event at Williams College and were able to easily walk there. There are plenty of shops and restaurants along the way. The area is beautiful. The space is amazing. Perfect for couples. We appreciated the treats and milk. The host was responsive to the only question we had and answered everything immediately. The instructions are exquisite and well planned. If you are in the area this is a great find.

4.93 out of 5 average rating, 73 reviews

Home in Cheshire

Berkshire County modern home + pool

DanielaRating, 5 stars4 days ago

Kelsey is flexible and responsive. You can tell she thought about how to curate a great stay by all of the amenities and presentation of the house. It’s cozy! Kelsey does have house rules but they’re not overbearing and if anything it was nice to have clear expectations communicated from the beginning.

4.86 out of 5 average rating, 29 reviews

Farm stay in New Lebanon

1800s Carriage house in Berkshires / Hudson Valley

KarenRating, 5 stars3 weeks ago

A lovely spot with a well maintained, extremely clean, spacious apartment. It was very well appointed, especially the kitchen and bathroom. Anything you needed was there. Great bed and comfortable furniture. Close to a few good restaurants and a wonderful farmers market. I would return in a minute.