Vacation rentals in New Lebanon

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in New Lebanon

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

0 of 0 items showing

1 of 3 pages

Superhost

A rustic cabin is nestled in a wooded area, featuring a bright red front door and a spacious deck. Surrounding the deck, lush greenery provides a natural backdrop, and a cozy seating area is visible on the porch. A fire pit with stones is situated in the foreground.

Cabin in Stephentown

4.86 out of 5 average rating, 290 reviews

Cabin in the woods w cedar Hot Tub + private pond

The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.

Top guest favorite

A cozy outdoor seating area is highlighted by a stone fire pit, with flames dancing above a bed of volcanic rocks. In the background, a high-definition TV displays a sports event. Barstools and a wooden structure suggest a welcoming spot to relax.

Apartment in Petersburgh

4.88 out of 5 average rating, 186 reviews

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.

Top guest favorite

Home in Canaan

5 out of 5 average rating, 66 reviews

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

Welcome to our little slice of heaven upstate. Located just a 5-minute drive to the MA border, a stay at our home in Canaan, NY means access to the best of both Columbia County and the Berkshires. In the summer, enjoy the private Adams Point Beach on Queechy Lake and easy access to Tanglewood. In the winter, explore 4 different local ski resorts and curl up by the cozy wood stove. In between, enjoy the peaceful pond views and secluded location on a dirt road. We can't wait to welcome you!

Top guest favorite

A modern cabin features a striking facade with large windows, surrounded by colorful trees. An outdoor deck contains multiple seating areas, including lounge chairs and a dining table. A wood-fired hot tub is situated nearby, surrounded by landscaped greenery and gravel pathways.

Cabin in East Nassau

5 out of 5 average rating, 46 reviews

Luxury Cabin | Breathtaking Views & Outdoor Fun

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, freshwater lake only locals know about. 2.5 hrs from NYC and from Boston. Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit and chairs, Webber Grill, radiant floor, optional Tiny Home, and EV charging!

Top guest favorite

An open studio space reveals a kitchenette with modern appliances, including a refrigerator and microwave. A wooden bar with stools is positioned next to a soft seating area. Natural light fills the room through a window, highlighting the rustic wooden beams above.

Cabin in Canaan

4.99 out of 5 average rating, 253 reviews

Rustic Barn Studio Apartment

Built from a saved, moved, & reconstructed 1850s- era barn from a former local dairy farm, this upstairs studio space features views of the Berkshire Mountains and walking paths on the 5 acre grounds. 20 mins from Jiminy Peak. 20 mins from Tanglewood Music Center. The space has a queen bed, sofa, kitchen area with fridge, sink, oven, stove, microwave, Keurig and coffee, toaster, and cooking essentials. **EV Charging Station coming sometime summer of 2023. We'll update when available.

Top guest favorite

A tranquil pond is framed by lush greenery and trees, with the surrounding landscape reflecting the natural beauty of the Berkshires. The clear sky complements the serene atmosphere, while the pond's surface offers a glimpse of the surrounding nature.

Farm stay in New Lebanon

5 out of 5 average rating, 19 reviews

NEW RENO - Chalet-style farm loft near Tanglewood

Welcome to Shaker Meadows, a historic 18th century Berkshires farm. This newly renovated chalet-style loft in the farm’s 1940s creamery has a full kitchen, & deck looking out onto the Berkshire mountains. Explore winding paths around 50 acres of farmland & hills or drive 10 mins to Hancock Shaker Village, 15 mins to Tanglewood/Jiminy Peak—a wonderful base for exploring the art, music, and history of the Berkshires. Great for couples, families, & solo adventurers. Kid- and pet-friendly.

Guest favorite

Cottage in New Lebanon

4.95 out of 5 average rating, 193 reviews

The Writer's Cottage

The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and table.

Top guest favorite

A wooden sign with the text 'BITTERSWEET FARM' is displayed prominently. Below the sign, a flower bed contains vibrant orange and yellow marigolds, adding a touch of color to the entrance. The surrounding grassy area is well-maintained, enhancing the welcoming appearance of the farm.

Farm stay in Pittsfield

4.99 out of 5 average rating, 221 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.

Top guest favorite

A colorful circular rug with a vibrant pattern is placed on a smooth bamboo floor. Natural light highlights the textures of the space, while a wooden staircase leads into the studio apartment. The overall layout showcases an inviting and dynamic atmosphere.

Apartment in Troy

4.93 out of 5 average rating, 443 reviews

Stunning studio in the heart of Troy: Raven's Den

Raven's Den is a large studio apartment with a queen sized bed, full kitchen, and an extra-deep bathtub. It is an open plan room that can be configured as needed, featuring two "aerial silk" hammocks that double as swings. It's in the heart of Downtown Troy, close to RPI, EMPAC, The Troy Music Hall, The Farmers Market, and the Takk House. Whether you need a cozy romantic getaway or simply a clean, fresh, place to lay your head, Raven's Den could be for you.

Top guest favorite

A wooden deck is surrounded by lush greenery, overlooking a serene natural landscape. Outdoor seating is provided, featuring a coffee table and comfortable chairs. A grill is visible nearby, situated against a backdrop of trees and hills, creating a peaceful retreat.

Home in Canaan

4.96 out of 5 average rating, 55 reviews

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

SUMMER: Stay includes: Access to Queechy Lake’s private beach. Sprawl out in this charming home that’s both private and close to everything! Discover everything this ALL SEASON Berkshires/Hudson Valley home has to offer. From skiing to Tanglewood, local farms to wineries, you’re close to it all! Relax in the hot tub lakeside while watching the beavers, curl up by the wood-burning stove, or play a game of pool. You’ll never want to leave!

Superhost

A wooden deck with a railing features flower pots at each end. An umbrella provides shade over a spot for seating. The section below the deck includes a stone path leading to the yard, framed by greenery and trees in the background.

Apartment in New Lebanon

4.78 out of 5 average rating, 18 reviews

A Sacred Place

A place that has a history of love. It’s cozy and it’s on beautiful family land in a central location . You can enjoy all four seasons here and all kinds of interests . With near by activity’s including skiing, hiking, lakes , fishing , horseback riding, museums, farmers markets, health and Yoga retreat center, and much more! Great Market , a couple cafes and restaurants right in town and plenty more.

Top guest favorite

A green, spacious yard features two lounge chairs positioned near a fire pit, surrounded by lush grass and vibrant flowering plants. The farmhouse stands in the background, complemented by a rustic barn and mature trees enhancing the natural setting.

Loft in East Nassau

4.99 out of 5 average rating, 181 reviews

Dog Friendly Farm

Welcome to The June Arthur Farm! This beautiful spot has a long agricultural history. It hasn't been in production for the past 40 years but we're slowly bringing it back to life. It's once again producing good, happy, Hudson Valley food: eggs, fruit, lamb, and beef. We hope you'll come visit us. Note for the skiers out there: We're 20 minutes from Jiminy Peak!

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for New Lebanon vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in New Lebanon

Top guest favorite

Chalet in Canaan

5 out of 5 average rating, 12 reviews

SRC-Hudson Valley/Berkshires Cultural Corridor

CariRating, 5 stars5 months ago

If you're thinking about booking Kristen's Chalet - do not hesitate! Book it - you won't be disappointed. The house has ample room to spread out with your family. We enjoyed our Christmas dinner at the dining table and afterwards, we were able to watch a movie together. The location was perfect for us to go out every day and explore - Red Lion Inn, The Mount and several other towns. We had to make plans to stay in so we could enjoy the beautiful Chalet for an evening. We can not wait to return and enjoy this beautiful home. ♡

Guest favorite

The spacious interior features high wooden beams and a stone fireplace at its center. Natural light fills the area through large windows, highlighting the open floor plan. A loft area is visible above, and comfortable seating arrangements support relaxation and gatherings.

Farm stay in New Lebanon

4.95 out of 5 average rating, 226 reviews

Barn Stay at Shadowbrook Farm

MarthaRating, 5 stars4 weeks ago

The place is private with nice outdoor and indoor space, well outfitted. I wish we had had more time there.

Guest favorite

A serene view of a creek surrounded by trees displaying autumn foliage. The water reflects the colorful leaves and the clear sky, creating a tranquil atmosphere. Rocks line the creek's edge, offering a natural contrast to the vibrant scenery.

Cottage in Malden Bridge

4.96 out of 5 average rating, 25 reviews

Cozy, charming cottage by the creek w/2 queen beds

TanyaRating, 5 stars1 week ago

Martha made our stay very welcoming. We had sold our home and wanted to stay in the area to be with our son and family for a week longer before heading out of state to our new home. The cottage was a ver quiet and peaceful time. Much needed after all the packing and moving we had done. Weather was not the best for being outside much but nights we could we enjoyed the fire pit . Thank you again for the cookies and the warm invite you gave us while there .

Top guest favorite

A winding gravel path leads through a vibrant field of yellow wildflowers. The landscape is framed by a backdrop of tall trees and historic stone buildings, offering a glimpse into the serene environment of a former Shaker settlement.

Place to stay in New Lebanon

5 out of 5 average rating, 27 reviews

20 minutes to Tanglewood

CassidyRating, 5 stars4 months ago

this is a beautiful house, view, and kitchen! we had a wonderful stay and hopefully will be back! the house was very clean and neatly organized i loved the interior design. just all around a great stay and i would definitely recommend!

Guest favorite

Cabin in Canaan

5 out of 5 average rating, 16 reviews

The Hideaway

RogierRating, 5 stars3 weeks ago

We (2 people and dog) stayed 4 nights at Julie's place. It is a true hideaway, quiet, serene, comfortable. It was a perfect base for us to venture out and discover all the beauty of Columbia County. Thank you, Rogier & Jo

Cabin in Stephentown

4.81 out of 5 average rating, 21 reviews

Cabin Nestled in the Pines (New Arcade Machine!)

DanRating, 5 stars2 weeks ago

Georgianna's place was just what I was looking for. Rustic, secluded, and reasonably priced. Kitchen cookware was lacking a little bit, only a few stainless pans which can be a bit difficult to cook on, but that seems to be pretty typical with short term rentals. Overall everything was just as advertised and I would stay again.

A stone arrangement serves as a rustic seating area, with several flat stones stacked for stability. The surrounding area features natural earth tones and scattered greenery, while a fire pit containing wooden logs is set in the background.

Home in Lenox

5 out of 5 average rating, 4 reviews

Spacious Guest House with Pool and Walk-in Shower

JessicaRating, 5 stars1 week ago

I loved my stay in the Berkshires at Siobhan’s place. The space was clean, spacious, and perfect for a quick work trip in the area. Fun walks right from the guest house and lots to explore in the area. Highly recommend!

Farm stay in Adams

5 out of 5 average rating, 4 reviews

Berkshires/Pet Friendly farm stay w/mountain views

SarahRating, 5 stars1 week ago

We had a great week full of hiking at Mt. Greylock and walking the local rail trail with our pups! Jessica’s place was a perfect touch down for everything we wanted to do. The camper felt private and cozy, a perfect place to relax and view beautiful scenery from the field. Getting to see the horses was a plus and our dogs loved hanging in the back yard. The camper was clean, comfortable and Jessica was very accommodating, making sure we had everything we needed! This is a place we would definitely come back to if we are in Adams again!

Show all

Vacation rentals in New Lebanon

Top-rated vacation rentals in New Lebanon

Vacation rentals for every style

Popular amenities for New Lebanon vacation rentals

Other great vacation rentals in New Lebanon

Destinations to explore