Bed and breakfast holiday rentals in Lenox

Hospitality in the Berkshire Woods

Enjoy a rustic wooded retreat up in the cool Berkshire hills, surrounded by nature and wildlife, in a quiet, secluded, safe and peaceful setting, yet very close to top-notch cultural and recreational attractions. Nearby trails, pristine lakes and woods offer hiking, swimming and cycling. Experience 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. Breakfast included!

Maple House, Birch Room

Enjoy a relaxing visit to a romantic Victorian home. Located in the Berkshires village of Norfolk, a 2 minute walk from the Yale Summer School of Music and Art and music venue Infinity Hall, this classic features the Birch Room decorated with original watercolors, a new queen Leesa bed, high speed wi-fi, a lovely shared bath with claw-foot tub, and a decorative fireplace. You will enjoy a shared wrap around open porch overlooking the gardens, and a cozy second floor sun porch with sunset views.

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.

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.

Hudson, NY, 1br - 2 queen - sale

FREE private parking. - Late Check-in: Until 12am / Winter: Breakfast is not included - We currently do NOT provide transportation - Same Day: Allow 2 hour prep. Private staircase - FREE WIFI - Built in 1848, HISTORIC - Be good with winding stairs (have no mobility issues) - Work remote! Private back porch doors. 2 double mattress queen beds. Smoking on porch. No pets. Kitchen not included. Wares provided. Full bathroom. Microwave & Fridge & Ice Compartment Check-in starts: 4PM

Welcome to the "Red Bridge Cottage"

Welcome to "The Red Bridge Cottage" a 2 minute walk to the Kinderhook Creek (a Hudson River estuary) with the best trout fishing! This newly renovated cottage has all new kitchen appliances including a new washer and dryer. Comforts include: Central AC & whirlpool tub! Locally and only 3 miles away is the Empire State Bike Trail - a 750 mile trail connecting urban centers, village main streets and rural communities with informational boards on the interesting local wildlife.

Serene Suite near Skiing, Walk to Restaurants

Hillsdale’s Hygge Hideaway...Enjoy a peaceful, serene suite with all the comforts of home. Private entrance, with ample parking for multiple cars so you can meet up...perfectly located where the Hudson Valley meets the Berkshires. Just 8 miles east from the Taconic State Parkway, located in the center of the Historic Hamlet of Hillsdale, NY. Walk to unique shops, a cooking school, restaurants and a brewery, a full service grocery store, wine and liquor store and more.

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.

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.

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

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.

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!