Holiday rentals in West Lebanon

Luxury Cabin | Fall Foliage, & 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 and chairs, Webber Grill, radiant floor, WFH space, and EV charging!

Guest Suite in Old Chatham Hunt Country

Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

The Bear's Den

Connecting with nature doesn't mean you have to rough it. The Bear's Den 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 Hawk's Nest & The Owl's Nest. 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.

Newly Renovated Red Door Annex

Private keypad entrance with parking. Large bedroom with full bathroom. The spacious room features a high-end queen bed and a small table for dining and working, a small frig, microwave, toaster oven, and pour-over coffee in a nook outside the bedroom. Popcorn, oatmeal 1/2 and 1/2 are provided. The Annex is in a tranquil neighborhood between Great Barrington and Williamstown/North Adams and ski areas.1 mile to Berkshire Medical Center. 20 minutes to Lenox. Fire Pit.

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.

The Red House

Welcome to our historic and charming home, tucked away on 50 acres of beautiful, serene woodland. Built in 1840, our 2200 square foot residence combines the authenticity of centuries-old wood beams with cozy, comfortable interiors. The Red House is close to the charming towns of the Hudson Valley: Chatham, Kinderhook, Ghent and Hudson. There is also easy access to Tanglewood, Jacob's Pillow, Mass MOCA, Williamstown and Tannery Pond.

The Cabin at Whispering Pines

Now with satellite WIFI, the Cabin at Whispering Pines is a 2 bed/1 bath private home set on 34 acres of mostly forest w/ trails outside that take you through our property, over a babbling brook & right into a 447 acre nature preserve. The cabin is perfect for nature lovers who also want proximity to local ski resorts, Lebanon Valley Speedway, Tanglewood, Albany, Chatham, Great Barrington, or Pittsfield.

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.

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!