Bed and breakfast holiday rentals in Lenox

Hospitality in the Berkshire Woods

“This is a REAL Bed & Breakfast!” “Like a boutique hotel, only more personal.” Enjoy a wooded retreat up in the cool Berkshire hills, surrounded by nature and wildlife, in a quiet, secluded, safe and peaceful setting, yet close to top-notch cultural and recreational attractions. Experience a fresh-air escape with the absence of mechanical sounds and the centering presence of rustling leaves, birdsong, and owls hooting at night. Behold a star-studded black night sky without artificial light.

Value · Location · TV

Large guest suite w/private bath in the Berkshires

A wonderful welcoming house in a beautiful residential neighborhood with no occupancy taxes! We are 15-25 minutes from Tanglewood, Kripalu, Mt Greylock, the Rockwell Museum, MassMoCA, skiing and hiking. Our home is centrally located to all of the fun things to do in the Berkshires. We've lived here for over 20 years and are happy to provide helpful insights for your stay. One of the reasons we love the Berkshires is that each season offers wonderfully unique experiences for any visitor.

Location · Value · Hiking

Hudson, NY, 1br on 2nd floor - 2 queen - full bath

1BR with private full bath - 2 queen size beds - On second floor FREE private parking. - Check-in: 4pm until 12am / Breakfast is not included - We currently do NOT provide transportation - Same Day: Allow 2 hour prep. time - Private staircase - FREE WIFI - Built in 1848 - HISTORIC - TAKE HEED: Be good with winding stairs (have no mobility issues) - Work remote! Private back porch doors. Smoking on porch. No pets. Kitchen not included. Wares provided. Microwave/Fridge & Ice Compartment

Location · Value · Backyard

Brick Row House in the Woods, private 2nd floor

Looking for the best price to stay in a historic Hudson Valley townhouse? Just 15 minutes from Hudson, NY is a private second-floor suite above an artist’s studio—bedroom, living room and bathroom all to yourself. Hosted by a top-rated Superhost known for her glowing reviews and exceptional hospitality, you'll enjoy a continental breakfast, easy self-check-in, and spotlessly cleaned rooms. The sunlit space and garden is perfect for meditation, journaling, studying, or simply unwinding.

Value · Family · Walkability

Whistler's Inn/The Petite Chambre (#11)

Whistler’s Inn is an 1870 English Tudor mansion in the heart of Lenox near Tanglewood, Shakespeare & Co., and all of the Berkshires’ most popular cultural venues. The home was once owned by Mr. and Mrs. Ross Wynans Whistler, railroad tycoon and nephew of the painter, James M. Whistler. Whistler’s Inn captures the warmth, comfort, and elegance of a bygone era. The inn has been featured on National T.V. - The Travel Channel and Fodor’s Bed and Breakfast Country Inns.

Location · Family · Pets

Arnold Farmhouse (Italianate - private bath)

Room with an attached bathroom and private entrance. Enjoy the porch, garden, honey bees, the old farm & fields, situated on the Valatie Kill in a quaint hamlet. The AH Bike Trail is just around the corner. If you come by bike, we can safely store the bike in the garage opposite the barn. Larkin Hill, Kinderhook Creek & Hunt Club are close. Schodack Island state park is 15 min. Van Buren house is 15 also. It is a wonderful spot to get some real fresh air.

Location · Family · Access

Stissing Lake House | Hudson Valley Lake Front

Whether you're here for a Stissing House wedding, a family summer, or a month by the lake — Stissing Lake House is your private Hudson Valley base. Swim from the dock. Sip champagne on the porch. Walk the mountain trails before the rehearsal dinner. This is a house made for celebration — spacious, romantic, and quietly grand. Kayaks, paddleboards, chef's kitchen, firepit. 6-bedroom Victorian overlooking a 70-acre spring-fed lake. Sleeps 14. Just 90 miles from NYC.

Value · Location · Comfort

The Sara Tracy House, Whitman Room

A beautiful home located in historic Lansingburgh, NY.; Downtown Troy 3 miles, Albany 10 miles, Saratoga Springs, Massachusetts and Vermont 30 miles. The setting is urban, eclectic, with grit. If you love history, architecture, art and antiques you'll love this place. If you are looking for a serene, upscale setting, this isn't the place for you. This home, built around 1825, is being restored in phases. Dog friendly. Private Baths, Central Air, Wi-Fi, Roku

Value · Location · Heating

Private Room and Bathroom - Clean, & Spacious

Hi, I'm Isla, This large bedroom has a Queen sized bed, a Sofa, TV, an Office’s desk and a private bathroom with shower. You will have use of the spacious kitchen and dining room area. The Townhouse is located in a cull de sac in a private community, so it is very quiet and safe. Includes a spacious, clean and bright kitchen fully stocked with pots, pans and utensils. Conveniently located close to everything the Berkshires has to offer.

Family · Value · Check-in

Serene Suite: Hudson & Berkshires, Walk to Brewery

A peaceful, highly rated private suite in the heart of historic Hillsdale, where the Hudson Valley meets the Berkshires. Walk to shops, restaurants, a brewery, cooking school, grocery, wine and liquor store. Minutes to Hilltown, the Harlem Valley Rail Trail, scenic hikes, and beautiful drives, with galleries, antiques, live music, and cultural gems nearby. A serene, perfectly located home base for spring dining, exploring, and unwinding.

Family · Location · Wi-Fi

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

Location · Value · Breakfast

Charming Eyebrow Colonial North Chatham, NY

Hike, bike, explore, experience peaceful farmlands and gardens in the delightful hamlet of North Chatham. Enjoy the entire 2nd floor guest suite with king size bed and private bath including shower. A special place set off from the main road. Convenient to New York State Thruway 90, 87, Taconic Parkway, Albany, Boston, the Berkshires, New England and the Empire State Trail.

Value · Family · Solo travel