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!

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.

The Lily House - Liv's Garden Room

Set in the historic district of Suffield, CT, this charming Victorian home offers a lovely place to stay as you journey through a quaint New England town. It has well appointed rooms, a beautiful wrap-around front porch and several gardens with walking paths. Just a short walk away from fine and casual dining, parks, the “Walk of Homes” as well as Suffield Academy. Our convenient location is only five miles from Bradley Int'l Airport and minutes from both Hartford CT, and Springfield MA.

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

FREE private parking. - Late Check-in: 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. 2 QUEEN SIZE BEDS - Smoking on porch. No pets. Kitchen not included. Wares provided. Full bathroom. Microwave & Fridge & Ice Compartment Check-in starts: 4PM

~Serene Barn Retreat~

Peaceful, romantic retreat in this stunningly large, 1850's remodeled barn apartment. The historic barn is nestled into hundrends of acres of Nature Conservency. Many old maple and pine trees, hiking trails and breathtaking views will welcome you along the the drive here. If you'd like to book a healing retreat I offer Reiki sessions to guests. Inquire when you book. *Mount Snow is 35 minutes away. Okemo, Stratton, Bromley and Magic is 1 hour away and Stratton is 1 hour away.

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.

Hampshire Room

Welcome! Our Hampshire Room is a comfortable private room w/ a brand new king bed, a laptop-friendly workspace, Wi-fi, and 40" flat screen. Conveniently next to bathroom. Convenient access: - MGM Casino-7 min - Bradley Airport-15 min - Eastern States Exposition, home of The Big E-5 min - Basketball Hall of Fame-8 min - Six Flags New England-10 min TWO extremely friendly cats, Tigger & Pounce will greet you and permit oodles of loving.

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!

Dove House on Trannery Brook in Woodstock

The Morning Glory B&B is located in a beautiful colonial house nestled right in the town of Woodstock, New York. it borders the Comeau property. There is easy access to the wonderful forested trails on the town's 72 wild acres; Overlook mountain trail and Tibet monastery right in town. unique shops and fine restaurants are walk to reach...

The Carriage Barn

Situated on a 1792 Vermont farmstead, the original Carriage Barn is a thoughtfully renovated 2-bedroom cottage that blends historic charm with colorful, comfortable design. Located just 10 minutes from Brattleboro and all that Southern Vermont has to offer, it’s a perfect home base for a cozy New England escape.