Bed and breakfast holiday rentals in Lenox

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Top-rated bed and breakfast rentals in Lenox

Guests agree: these bed and breakfast rentals are highly rated for location, cleanliness and more.

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Superhost

Private room in Sandisfield

4.93 out of 5 average rating, 141 reviews

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!

Cabin in Sheffield

4.78 out of 5 average rating, 74 reviews

The Brook House at Race Brook Lodge

Cozy, private brookside bungalow sleeps four. Bright studio living space with queen and two twin beds, full kitchen, breakfast nook. Beyond the shady porch, enjoy rolling lawn, hammocks, abundant hiking. The Brook House is situated on the grounds of Race Brook Lodge, with breakfast, swimming pool, lawn games, and great hiking right on the property, including direct access to Race Brook Falls. Also just steps away from the Stagecoach Tavern Restaurant and Barnspace and DCSC performance spaces.

Top guest favourite

Private room in North Chatham

4.93 out of 5 average rating, 350 reviews

Arnold Farmhouse (Italianate - private bath)

Private entrance to room with an attached bathroom. Enjoy the porch, garden, honey bees, the old farm/fields., situated on the bank of the Valatie Kill in the quaint hamlet. The AH Bike Trail is just around the corner, Larkin Hill, Kinderhook Creek & Hunt Club. We are 30 minutes from Albany or Hudson on excellent roads. Schodack Island is 15 min. Van Buren house is 15 also. Jiminy Peak Ski is a 30 min. It is a wonderful to get some real fresh air - good for couples, solo, and business.

Guest favourite

Flat in Rexford

4.96 out of 5 average rating, 361 reviews

Need a Getaway??

It’s Fall foliage season! Apple picking & hiking, This ideal location is perfect for leaf peeping, visiting family, business travelers, college visits and lots of outdoor recreation. Located about 20 minutes from Saratoga’s city line. This beautiful, quiet and spacious apartment on the 2nd floor overlooks several acres of land. Also, a perfect halfway point between Canada and New York City. We offer complimentary coffee, eggs & pancake mix to cook in the full size kitchen. Pool is heated!

Top guest favourite

Private room in Pittsfield

4.98 out of 5 average rating, 422 reviews

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.

Superhost

Private room in Hudson

4.84 out of 5 average rating, 785 reviews

Hudson, NY, 1br - 2 queen - July sale

Free private parking. - Now: Late Check-in: Until 12am / Mutual Agreement - Please allow 1 hour prep. Private staircase - FREE WIFI - Built originally in 1848, one window facing crescent driveway - Be good with winding stairs (have no mobility issues) - Sunny big room. Perfect to work remote. Private back porch doors. 2 double mattress queen beds. Smoking on porch. No pets. Kitchen not included. Wares provided. Full bathroom. Microwave & Silent Fridge Same price: 1 to 4 guests!

Top guest favourite

Private room in Athens

4.96 out of 5 average rating, 389 reviews

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.

Top guest favourite

Townhouse in Hudson

4.95 out of 5 average rating, 216 reviews

Palazzo Hudson: Luxury Home with Pool, Spa, Sauna

Welcome to Palazzo Hudson! The only private vacation home in the town of Hudson with a chef's kitchen, seasonal in-ground pool, deluxe sauna, cedar hot tub & a separate poolhouse library lounge. A home for all seasons, you'll experience inspiration and relaxation from the warm, light-filled rooms, curated art, books, music, luxury spa features, and outdoor deck, patios, and gardens. A quick stroll to the restaurants, bars, cafes, and shops of Warren Street and the Upper Depot District.

Top guest favourite

Flat in Hillsdale

4.99 out of 5 average rating, 216 reviews

Serene Suite by Gt. Barrington, Hudson, Tanglewood

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.

Guest favourite

Private room in Troy

4.97 out of 5 average rating, 364 reviews

The Sara Tracy House, Eliot 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

Guest favourite

Private room in Tivoli

4.89 out of 5 average rating, 135 reviews

Suminski Innski- Room 7- 2 flights up/shared bath

The Suminski Innski is a 3-storied 19th century mansion, located right on the Hudson River. A great place for writers, artists, musicians, hikers, and friends. Room 7 has a queen bed and access to a shared bathroom; fresh breakfast is provided every morning! Join us on the front porch by Hudson river to watch the sun set in the Catskill mountains, or at the patio for grill & barbecue.

Top guest favourite

Guest house in Granby

4.98 out of 5 average rating, 837 reviews

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!