Holiday houses in Lebanon Springs

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Top-rated holiday rentals in Lebanon Springs

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Superhost

Cabin in Stephentown

4.86 out of 5 average rating, 291 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 favourite

Apartment in Petersburgh

4.88 out of 5 average rating, 187 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 favourite

Cabin in East Nassau

5 out of 5 average rating, 49 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 favourite

Cabin in Canaan

4.99 out of 5 average rating, 254 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.

Guest favourite

Farm stay in New Lebanon

4.91 out of 5 average rating, 22 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.

Top Guest favourite

Campervan/RV in East Nassau

5 out of 5 average rating, 33 reviews

The Hawk's Nest

Connecting with nature doesn't mean you have to rough it. The Hawk's Nest is a cozy campsite located in the heart of the Berkshires. 32 acres to explore and wildlife to watch. There is a hawks nest on the property and if timed right you can watch them hunt the field. Please also view , The Owl's Nest & The Bear's Den. All the same features but each are unique. Disclosure: We are a couple miles from Lebanon Speedway and some of the races can be loud. Extremely quiet otherwise.

Top Guest favourite

Farm stay in Pittsfield

4.99 out of 5 average rating, 229 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.

Guest favourite

Home in New Lebanon

4.94 out of 5 average rating, 32 reviews

Airy Upstate Getaway with a View

Welcome to your perfect getaway in New Lebanon! This open and spacious home offers stunning views of the New Lebanon Valley. Enjoy modern amenities throughout, ensuring a comfortable and enjoyable experience. Just a short drive away, you’ll find skiing adventures at Jiminy Peak and the enchanting ruins at Sassafras Farm, perfect for exploration. Unwind and reconnect with nature in this inviting retreat—your ideal home base for adventure and relaxation awaits!

Guest favourite

Apartment in New Lebanon

4.96 out of 5 average rating, 105 reviews

Airy apartment at the old boarding house

Distinctive 2-bedroom with lots of windows and light and a kind of shabby elegance. It's half of a Greek Revival house from 1900 on a country lane at the foot of the Berkshires. Enormous master bedroom with dressing room, 2nd bedroom with twin beds, lovely living room, separate dining room, full kitchen. Big covered front porch for eating outside, with grill, table and an acre of orchard outside too.

Superhost

Apartment in New Lebanon

4.8 out of 5 average rating, 20 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.

Guest favourite

Apartment in Lenox

4.88 out of 5 average rating, 191 reviews

Station House 1E Private Room & Bath

Our place is a central location in Berkshire County, short drive to restaurants and shops; art and culture, skiing and hiking also close by. You’ll love this former train station( next to the Housatonic RR tracks) which is on three acres between a chapel, the scenic Housatonic River and October Mountain. Our place is good for couples, solo adventurers, and business travelers.

Top Guest favourite

Loft in East Nassau

4.99 out of 5 average rating, 183 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!