Bed and breakfast in The Berkshires, MA

385 available b&b offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
The Berkshires, MA bed and breakfast
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

385 Bed and Breakfasts and Inn in The Berkshires, MA

Best The Berkshires, MA bed and breakfasts with breakfast included

The Revival House - The Berkshires, MA
No reviews

The Revival House

B&B, Adams
The Revival House B&B in Adams, Massachusetts offers convenient accommodation a short distance from the town centre, within walking distance of the Adams Theatre, the East Hoosac Quaker Meetinghouse, and the Susan B. Anthony Birthplace Museum.
This guest house provides free Wi-Fi, on-site parking, and sleeps two guests in one bathroom; a £100 damage deposit is required before check-in.
The Revival House - The Berkshires, MA
9.0 38 reviews

The Revival House

B&B, Adams
This Adams guest house is conveniently located within a 15-minute walk of both the Adams Theatre and the Berkshire Scenic Railway Museum, and under 2km from the East Hoosac Quaker Meetinghouse and the Susan B. Anthony Birthplace Museum.
The B&B offers free breakfast, on-site parking, and Wi-Fi in communal areas, plus a shared lounge and housekeeping on request; it is a non-smoking establishment.
The Nutmeg - The Berkshires, MA
9.4 442 reviews

The Nutmeg

B&B, Wilmington
This charming guest house is situated on a river in Wilmington, within 1.5 kilometres of the North Branch Deerfield River and Jim McGrath Gallery and Studio, and within 1.6 kilometres of Pettee Memorial Library and South Main Street. It has received excellent guest reviews, highlighting its peaceful location and friendly service.
The accommodation features a garden and picnic area, as well as a seasonal outdoor pool and a games room for entertainment. Guests can enjoy a cooked-to-order breakfast and free Wi-Fi in public areas.
The Trail In Adams - Berkshires’ Art Hotel - The Berkshires, MA
9.0 156 reviews

The Trail In Adams - Berkshires’ Art Hotel

B&B, Adams
This charming bed and breakfast is situated in the mountains of Adams, just 2 kilometres from both the Adams Theater and the Susan B. Anthony Birthplace Museum. It has been consistently rated as "very good" by previous guests, suggesting a comfortable and enjoyable stay.
The inn boasts a range of communal areas, including a garden and a library, perfect for relaxing and enjoying the peace and quiet. It also offers convenient amenities like free Wi-Fi, parking, and concierge services, ensuring a comfortable and hassle-free stay.

Best The Berkshires, MA bed and breakfasts with a garden

Historic Barn Stay At Gedney Farm - The Berkshires, MA
No reviews

Historic Barn Stay At Gedney Farm

B&B, New Marlborough
Gedney Farm is a premier boutique hotel experience located on 50 acres of scenic rolling pastures and high open meadows within the historic village of New Marlborough. This accommodation offers rooms with individually furnished decor, private bathrooms, and select rooms feature granite-surround wood-burning fireplaces or deep whirlpool tubs, with air conditioning and internet available for up to two guests.
Adorable 1 Bedroom Guesthouse In Country Setting. - The Berkshires, MA
9.4 42 reviews

Adorable 1 Bedroom Guesthouse In Country Setting.

B&B, Florida
This **detached house** offers a tranquil escape in a scenic valley, providing a peaceful contrast to Florida's busier locales, with proximity to the Deerfield River for water activities and the Berkshire East ski area for year-round adventures.
This **residence** accommodates up to two guests with one bedroom and one bathroom, featuring a fridge and microwave oven, and is ideally situated for exploring North Adams' cultural sites like Mass MoCA and the natural beauty of Mount Greylock, with opportunities for a digital detox due to limited mobile signal.
The Nutmeg - The Berkshires, MA
9.4 442 reviews

The Nutmeg

B&B, Wilmington
This charming guest house is situated on a river in Wilmington, within 1.5 kilometres of the North Branch Deerfield River and Jim McGrath Gallery and Studio, and within 1.6 kilometres of Pettee Memorial Library and South Main Street. It has received excellent guest reviews, highlighting its peaceful location and friendly service.
The accommodation features a garden and picnic area, as well as a seasonal outdoor pool and a games room for entertainment. Guests can enjoy a cooked-to-order breakfast and free Wi-Fi in public areas.
The Trail In Adams - Berkshires’ Art Hotel - The Berkshires, MA
9.0 156 reviews

The Trail In Adams - Berkshires’ Art Hotel

B&B, Adams
This charming bed and breakfast is situated in the mountains of Adams, just 2 kilometres from both the Adams Theater and the Susan B. Anthony Birthplace Museum. It has been consistently rated as "very good" by previous guests, suggesting a comfortable and enjoyable stay.
The inn boasts a range of communal areas, including a garden and a library, perfect for relaxing and enjoying the peace and quiet. It also offers convenient amenities like free Wi-Fi, parking, and concierge services, ensuring a comfortable and hassle-free stay.

Frequently asked questions about bed and breakfast in The Berkshires, MA

  • What are the must-see sights for first-time visitors on a day trip to Monts Berkshire?

    For a day trip, you can't miss the iconic Tanglewood Music Center in Lenox, with its beautiful grounds and world-renowned concerts. Then head to the charming town of Stockbridge to visit the Norman Rockwell Museum, showcasing the works of the famous American artist. And if you're looking for stunning views, a drive up to Mount Greylock, the highest point in Massachusetts, is a must.
  • What are the best bed and breakfasts in The Berkshires, MA?

    Among the B&Bs in The Berkshires, MA, Comfortable Living In 1870's House, Priv - Rm -#2 In Forest Clearing Home and Chambery Inn are the most popular ones.

  • In which districts of Monts Berkshire should you consider booking a bed and breakfast?

    The Berkshires has a lot of charming towns, but for a bed and breakfast stay, I'd recommend Lenox, Stockbridge, or Great Barrington. Each has a unique character and offers easy access to the region's attractions.
  • What are the best bed and breakfasts with a pool in The Berkshires, MA?

    Devonfield Inn, Oak And Spruce Holiday Inn Vacation Club and Oak N' Spruce Resort are the best B&Bs with a pool in The Berkshires, MA.

  • What is the typical weather in Monts Berkshire, and how does it affect outdoor plans?

    The Berkshires has four distinct seasons. Summers are warm and humid, perfect for hiking and outdoor activities. Autumn brings vibrant foliage, making it ideal for scenic drives and walks. Winters are cold and snowy, great for skiing and snowshoeing. Spring is a time of renewal with mild temperatures and blooming flowers.
  • What are the best bed and breakfasts with a jacuzzi in The Berkshires, MA?

    The best B&Bs with a jacuzzi in The Berkshires, MA are Chambery Inn, Devonfield Inn and Quiet Kid-friendly Country Home: Lower Level.

  • What dining options are recommended for solo travelers staying at bed and breakfasts in Monts Berkshire?

    Many bed and breakfasts offer breakfast, but for dinner, solo travellers can find great options in the area. The Red Lion Inn in Stockbridge has a lovely atmosphere and delicious food. In Lenox, the Wheatleigh is another excellent choice, offering a more upscale dining experience.
  • What are the best bed and breakfasts for families and kids in The Berkshires, MA?

    The best B&Bs for families and kids in The Berkshires, MA are Hospitality In The Berkshire Woods, Devonfield Inn and Peaceful Country Berkshire Getaway.

  • What are the best cultural activities and events in and around Monts Berkshire?

    The Berkshires are known for their cultural scene. Beyond Tanglewood, you can enjoy performances at the Jacob's Pillow Dance Festival in Becket, the Berkshire Theatre Group in Stockbridge, and the Mahaiwe Performing Arts Center in Great Barrington. The region also hosts numerous art festivals and exhibitions throughout the year.
  • What are the best pet friendly bed and breakfasts in The Berkshires, MA?

    The best pet friendly B&Bs in The Berkshires, MA are Chambery Inn, Devonfield Inn and Cozy Guesthouse Near Downtown - Lee.

  • Which hiking trails are recommended for exploring in and around Monts Berkshire?

    For a challenging hike with stunning views, try the Appalachian Trail section that runs through the Berkshires. For a more moderate hike, check out the Mount Everett Trail in South Egremont, offering panoramic views of the Taconic Range. And for a family-friendly option, the Bash Bish Falls Trail in Mount Washington is a great choice.
  • What are the best bed and breakfasts with parking in The Berkshires, MA?

    Comfortable Living In 1870's House, Priv - Rm -#2 In Forest Clearing Home and Chambery Inn are the best B&Bs with parking in The Berkshires, MA.

  • What amenities are commonly offered in bed and breakfasts in Monts Berkshire?

    Berkshire bed and breakfasts often offer a range of amenities, including a hearty breakfast, comfortable rooms with private bathrooms, and some even have fireplaces, outdoor seating, and gardens. Some may also offer extras like bicycles for exploring the area or access to a swimming pool.

Popular destinations

Best pet friendly The Berkshires, MA bed and breakfasts

Among the 385 accommodations in The Berkshires, MA, here are the 2 best pet friendly B&Bs

South Shire - The Berkshires, MA
No reviews

South Shire

B&B, Bennington
South Shire is conveniently located in the centre of Bennington, within walking distance of the Bennington Arts Guild Gallery, Harmon Hill, and Hemmings Motor News Car Lover's Convenience Store & Vehicle Display. The bed and breakfast offers a charming and comfortable stay in the heart of this historic town.
The guest house has a single bathroom and provides a restaurant on-site, free Wi-Fi, parking, air conditioning, and concierge services. Guests can enjoy a pet-friendly atmosphere, press services, and the option to arrange transfers through the hotel staff.
South Shire - The Berkshires, MA
9.0 346 reviews

South Shire

B&B, Bennington
South Shire is a charming bed and breakfast in Bennington, Vermont, located just two miles from the Bennington Battle Monument. The property enjoys excellent ratings for cleanliness, location, and overall experience.
The guest house offers one bedroom and bathroom, perfect for a couple or solo traveller. Guests can enjoy a range of amenities including a spa, fitness centre, bar, and garden, as well as access to a terrace, jacuzzi, and free parking.

Best The Berkshires, MA bed and breakfasts with laundry available

Your Private Berkshire Retreat 
 Is Back! - The Berkshires, MA
9.4 66 reviews

Your Private Berkshire Retreat Is Back!

B&B, Otis
Moosehaus B&B, a self-contained apartment in Otis, Massachusetts, enjoys a secluded 7-acre setting down a private drive, offering easy access to Tanglewood and Jacob's Pillow (distances vary, check specific driving times).
This two-bedroom guesthouse, sleeping four, provides a private entrance, garden access, a kitchen with fridge, freezer and microwave, plus basic supplies and parking; nearby attractions include hiking trails, ski slopes and lakes.

Highly Recommended Luxury Bed and Breakfasts in The Berkshires, MA

Treat yourself to custom alpine woodwork and elite personalized service at luxury mountain B&Bs in The Berkshires, MA.

Historic Barn Stay At Gedney Farm - The Berkshires, MA
No reviews

Historic Barn Stay At Gedney Farm

B&B, New Marlborough

Check Out Bed and Breakfasts in the City Centre in The Berkshires, MA

Wake up in the heart of it all; choose a charming, centrally located B&B in The Berkshires, MA and leave the taxis behind.

The Trail In Adams - Berkshires’ Art Hotel - The Berkshires, MA
9.0 156 reviews

The Trail In Adams - Berkshires’ Art Hotel

B&B, Adams
The Trail In Adams - Berkshires' Art Hotel - The Berkshires, MA
8.5 77 reviews

The Trail In Adams - Berkshires' Art Hotel

B&B, Adams
The Revival House - The Berkshires, MA
9.0 38 reviews

The Revival House

B&B, Adams
Your Private Berkshire Retreat 
 Is Back! - The Berkshires, MA
9.4 66 reviews

Your Private Berkshire Retreat Is Back!

B&B, Otis

Top-Rated Coastal Bed & Breakfasts in The Berkshires, MA

Enjoy a hearty morning breakfast and the sound of the waves before heading down to the beach from these charming The Berkshires, MA coastal B&Bs

South Shire - The Berkshires, MA
9.0 346 reviews

South Shire

B&B, Bennington

Top-Rated Bed and Breakfasts with a Pool in The Berkshires, MA

Plunge into a cool pool after working up a sweat on the wilderness trails at mountain B&Bs in The Berkshires, MA.

The Nutmeg - The Berkshires, MA
9.4 442 reviews

The Nutmeg

B&B, Wilmington

Best The Berkshires, MA bed and breakfasts with parking

Adorable 1 Bedroom Guesthouse In Country Setting. - The Berkshires, MA
9.4 42 reviews

Adorable 1 Bedroom Guesthouse In Country Setting.

B&B, Florida
The Trail In Adams - Berkshires' Art Hotel - The Berkshires, MA
8.5 77 reviews

The Trail In Adams - Berkshires' Art Hotel

B&B, Adams
South Shire - The Berkshires, MA
9.0 346 reviews

South Shire

B&B, Bennington
The Trail In Adams - Berkshires’ Art Hotel - The Berkshires, MA
9.0 156 reviews

The Trail In Adams - Berkshires’ Art Hotel

B&B, Adams
©2026 cozycozy.com