Vacation rentals with breakfast in Berkshire County

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

You want to pop out of bed, walk downstairs and be right on the mountain - this is the place to be. This Stylish 1BR, 1BA suite with an additional Pull Out Queen sleeps 4 comfortably. It sits RIGHT in the Thatcher Building in front of the MAIN ski lift in Village Center. You can not get better than that! All the convenience without the bustle. This large 650 sq ft condo features brand new decor meticulously maintained, and includes a full kitchen with all the amenities. As a guest, you will

Family · Location · Layout

All-Season Berkshires Escape: Ski, Hike, Swim

Explore the best of the Berkshires, then retire to this charming 4-bed, 2-bath New Marlborough home to lounge, grill, dine, and lay your heads. The Konkapot River runs next to this vacation rental, which abuts protected land and a nature preserve. Within 5 miles of the home, you can access the Gedney Farm wedding venue, warm-weather attractions like Lake Garfield Beach and the Appalachian Trail at Beartown State Forest, winter hotspots like Butternut Ski Area, and renowned farm-to-table dining.

Family · Location · Comfort

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.

Family · Value · Kitchen

Charming Victorian Farmhouse Bedroom 1

An Airbnb that's more like a B&B! Tastefully renovated Victorian farmhouse in West Stockbridge just outside Great Barrington's village of Housatonic. Minutes from Great Barrington center, Stockbridge, Lenox & Tanglewood. Hosted by Dee Dee & Eddie. Enjoy a CONTINENTAL BREAKFAST featuring fresh fruit in season, yogurt, granola, delicious Berkshire Mountain Bakery offerings, an assortment of coffees and teas & other goodies. Read our reviews to see for yourself why we are Airbnb Super Hosts.

Value · Location · Cleanliness

Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

Location · Value · Check-in

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 · Outdoor spaces

Serene Berkshire Room with breakfast

Charming room with breakfast included. This is a room in our home where we live. Private shower/bathtub/toilet and heat lamp. Netflix, Amazon and Roku in room. On 1st floor of comfortable, quiet house in rural setting. Geothermal heating and cooling. Nestled in Hudson Valley/Berkshires. Year-round cultural, scenic & recreational activities. Free pass to nearby private beach. Near 4 ski areas. Enjoy our nature trail & busy birdfeeders. 10 mins. from highway- 2.5 hours. from NYC & Boston.

Family · Location · Wifi

Historic New England with Sunset Views

This space is close to everything- easy access to hike, ski, snowboard, 5 minute drive to Tanglewood & Kripalu, Dining, Cafes, shops, art galleries, live music & more. Centrally located on Berkshire County main road [regularly salted & plowed during snow season] making it easy to get to wherever you're going. Enjoy westward facing kitchen, bathroom & bedroom window for beautiful sunset views of Lenox nature. Great cell & WiFi service. Private 2nd floor; staircase walk up.

Hospitality

Whistler's Inn/The Garden Room (#9)

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 · View · Check-in

2 Bed Berkshire Getaway @ Stephentown Hotel

Welcome to the Stephentown Hotel in the heart of the Berkshire & Taconic Mountains. Completely remodeled two bedroom apartment, brand new everything! Located on the 2nd FL. Large apartment, private arcade with (x3) real arcade games, private kitchen, soaking bathtub, bright and spacious with plenty of windows, ductless ACs, plus a Washer Dryer in-unit. Located minutes to Jiminy Peak! Outdoor area w/ fire pits, BBQ, picnic tables, outdoor games, etc.

Value · Location · Accuracy

Equestrian retreat

Quiet farm house just across the street from our Morgan horse farm is a perfect spot to relax while your visiting the Berkshires. Easy drive to ski areas and local attractions. Our house has an easy divide. The guest side has; Two bedrooms one queen room and one with a double bed. There is a shared bathroom and a warm welcoming den available for your enjoyment . We also invite you to visit Sebring Stables and enjoy our beautiful Morgan horses.

Family · Value · Skiing

Pittsfield. Large queen bedroom, second floor.

This 2nd floor bedroom is in the host's and her dog's home. Besides a queen bed with a comfortably firm foam mattress, it has a work table, sitting area, double closet, and large dresser with mirror. Guests have kitchen privileges, welcome access to living room tv, deck overlooking gardens, and basement laundry room. A mile away is lovely Onota Lake. It's only a short drive to downtown Pittsfield. Nearby are many cultural & natural sites.

Location · Value · Shared spaces