Bed and breakfast vacation rentals in Pioneer Valley

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!

Warm Country Home Minutes from Town

Comfortable, clean, quiet room and private bathroom. We are 10 minutes away from our vibrant downtown. You have access to the living and dining room, patio, yard, and nearby hiking trails. We love hosting and we take our hosting seriously to make our guests happy. Please understand that you are booking a homeshare listing, sharing some spaces with us if you choose to. Although our older home is “lived in," we work hard to make our home clean. We and our lovely cats are hoping to meet you!

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.

King suite, full breakfast, 5 stars

Bright room with king bed, cotton sheets, own bathroom, sleep sofa, and a private porch. We bring a breakfast to your door to start your day right - because it’s not just AirB! Tucked away below Deerfield Ridge: four minutes' drive to Deerfield Academy, Eaglebrook, Bement, and just 17 miles to Amherst or Northampton and their colleges. If you like a secluded spot, you will be happy here with us and we will respect your privacy. The entrance is the only shared space.

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.

New England Escape

We would love to have you stay at our home. ONLY 5 minutes from Old Sturbridge Village and the Brimfield Antique and Collectibles Show! Also, close to local breweries, tourist attractions, wedding destinations, the airports, and the 3 largest cities in MA. (one hour from both Logan International and Bradley International Airports.) Perfect for couples, singles, or business travelers.

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!

The Shepherd's Retreat

This in-law apartment is on the first floor of our 2 level home and has its own separate entrances. It features an open floor plan with galley kitchen and breakfast bar. This location has a peaceful relaxing atmosphere but with easy access to shopping, site seeing, hiking, and is minutes away from historic Bennington, Vt and the Berkshires (Mass Moca Museum).

Norton Hill BnB

Norton Hill BnB is a traditional BnB with a host on site in the heart of scenic Ashfield; The home is spacious and ideal for group and family gatherings. Common areas include the dining room, a parlor, living room, and a porch that overlooks the yard. Please fully review 'The Space' & 'House Rules' details prior to reserving for a party, or a pet.

Stuart Cottage/Minutes to Mohawk Ski Area

The Stuart Cottage is located on the grounds of the Mary Stuart House Bed and Breakfast. Owned by Mary and managed by Elizabeth, the cottage has one bedroom, wifi and plenty of charm...truly the perfect place to relax in a rustic, low-key location in the heart of the Litchfield Hills. Mohawk Mountain and Tyler lake are just a short car ride.

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.

The 1797 House/Locke bedroom along CT River

Welcome to the Captain Locke room in the historic 1797 House (its birth year) in one of America’s oldest English settlements. We now welcome the world to our home along the Connecticut River. Close to UMass, Mount Holyoke, Amherst, Smith and Hampshire colleges, as well as Northampton & I-91.