Bed and Breakfast and Inn in Stockbridge, MA

37 available b&b offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Stockbridge, MA B&B
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

37 Bed and Breakfasts and Inn in Stockbridge, MA

Best Stockbridge, MA bed and breakfasts with breakfast included

The Cornell Inn, Lenox & The Berkshires - Stockbridge, MA
9.0 1528 reviews

The Cornell Inn, Lenox & The Berkshires

B&B, Lenox
This charming bed and breakfast is situated in Lenox, just a short distance from the Boston Symphony Orchestra's Tanglewood Institute, and within easy reach of the town's restaurants. It boasts excellent user, location, and cleanliness ratings, making it a popular choice for travellers seeking a comfortable and enjoyable stay.
The guest house is set on four acres, offering a peaceful and secluded environment. Guests can enjoy a gourmet breakfast, relax on the private deck, or explore the gardens that connect to Kennedy Park.
The Inn At Stockbridge - Stockbridge, MA
8.8 4 reviews

The Inn At Stockbridge

B&B, Stockbridge
This Stockbridge guesthouse offers a convenient base, situated 5.9 kilometres from Cranwell Spa & Golf Club, 6.9 kilometres from the Norman Rockwell Museum, and 9 kilometres from Tanglewood Musical Center.
Guests can enjoy family rooms with air conditioning and balconies, a fitness centre, an outdoor swimming pool, and a diverse breakfast menu, with complimentary WiFi available in public areas.
Shaker Mill Inn - Stockbridge, MA
9.5 572 reviews

Shaker Mill Inn

B&B, West Stockbridge
Shaker Mill Inn is situated in West Stockbridge, just under 6.5 kilometres from Tanglewood and the Norman Rockwell Museum. The inn has consistently received excellent ratings for location, cleanliness and overall experience.
The inn offers a range of rooms, all with en-suite facilities. Guests can enjoy a continental breakfast, relax in the garden or by the outdoor fireplace, and take advantage of the on-site spa, Jacuzzi and massage services.
Devonfield Inn - Stockbridge, MA
9.9 153 reviews

Devonfield Inn

B&B, Lee
This charming bed and breakfast is conveniently located in Lee, Massachusetts, just a short distance from Greenock Golf Club, Tanglewood Music Center, and the Norman Rockwell Museum. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This country house offers one bedroom and one bathroom, accommodating up to two guests. Enjoy a range of amenities including a swimming pool, jacuzzi, tennis court, restaurant, and a fully equipped kitchen, along with a spacious garden and terrace for relaxing and enjoying the beautiful surroundings.

Best Stockbridge, MA bed and breakfasts with a garden

Standard Queen At Hideaway Inn Lenox - Stockbridge, MA
10 3 reviews

Standard Queen At Hideaway Inn Lenox

B&B, Lenox
This boutique inn is located in central Lenox, Massachusetts, offering direct walking access to shops and restaurants, and is only 3 kilometres from Tanglewood.
This pet and family-friendly establishment offers 1 bedroom and 1 bathroom for up to 2 guests, featuring air conditioning, Wi-Fi, a garden, and parking, with communal areas including a wraparound porch, a living room with games, and an outdoor fire pit, plus a dedicated children's playroom.
Catamount - Pets Allowed-suite-standard-salle De B - Stockbridge, MA
10 11 reviews

Catamount - Pets Allowed-suite-standard-salle De B

B&B, West Stockbridge
The Shaker Mill Inn, a pet-friendly guesthouse in West Stockbridge, Massachusetts, offers convenient access to local attractions; precise distances require further clarification.
This ground-floor room at the Shaker Mill Inn features two queen beds, a sofa bed, a private entrance, and an outdoor dining area, comfortably sleeping four guests and connecting to an adjacent room for larger groups.
Sunny Riverside Apartment - Stockbridge, MA
9.8 228 reviews

Sunny Riverside Apartment

B&B, Lee
This charming garden apartment is located in Lee, Massachusetts, just a short drive from Stockbridge, the Clark Museum, Mass MOCA, and Kripalu, offering easy access to the region's cultural attractions. The apartment enjoys excellent ratings for location, cleanliness, and overall experience.
The apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. Guests can enjoy a fully equipped kitchen, a private entrance, and a garden with river views, allowing for a relaxing and comfortable stay.
Walkable Stockbridge + Headed Pool & Bike Rentals - Stockbridge, MA
No reviews

Walkable Stockbridge + Headed Pool & Bike Rentals

B&B, Stockbridge
The Red Lion Inn, a guesthouse in Stockbridge, Massachusetts, is centrally located in the town centre, within 3.2km of the Norman Rockwell Museum and walking distance of local shops and galleries.
This pet-friendly inn offers two bedrooms, one bathroom, and sleeps six guests, boasting a heated outdoor pool, hot tub, fitness centre, and complimentary bike rentals, alongside unique dining venues and regular entertainment such as live music and art exhibitions.

Frequently Asked Questions about bed and breakfast in Stockbridge, MA

  • What are the must-see sights for first-time visitors on a day trip to Stockbridge, MA region?

    For a first-time visit, you definitely want to see the Norman Rockwell Museum, which showcases his iconic American art. Then, head over to the beautiful Tanglewood Music Center to enjoy the stunning architecture and the serene atmosphere, especially if there's a concert happening. You can also pop into the Stockbridge Library, a charming building with a rich history.
  • What are the best bed and breakfasts in Stockbridge, MA?

  • What weather can travelers expect when exploring nature in Stockbridge, MA?

    Stockbridge has four distinct seasons. Summers are warm and humid, perfect for hiking and exploring the Berkshires. Autumn is a beautiful time with vibrant foliage. Winters are cold and snowy, ideal for skiing and snowshoeing. Spring brings mild temperatures and blooming flowers, making it a great time for walks in the countryside.
  • What are the best bed and breakfasts with a pool in Stockbridge, MA?

  • What outdoor activities can visitors enjoy in and around Stockbridge, MA?

    Stockbridge is a great place for outdoor activities. You can hike the trails of the Mount Everett State Forest, go kayaking on the Stockbridge Bowl, or visit the Chesterwood, the former estate of sculptor Daniel Chester French, and explore its beautiful gardens. And don't forget to visit the Naumkeag estate, a stunning example of American architecture and gardens.
  • What are the best bed and breakfasts for families and kids in Stockbridge, MA?

    The best B&B for families and kids in Stockbridge, MA is The Cottage.

  • What famous cities can be easily accessed from Stockbridge, MA?

    Stockbridge is conveniently located near several famous cities. You can easily reach Boston, New York City, and Albany by car, all within a few hours' drive. And if you're looking for a shorter trip, Pittsfield is just a short drive away and offers a variety of attractions.
  • What are the best pet friendly bed and breakfasts in Stockbridge, MA?

  • What local breakfast specialties can you enjoy in Stockbridge, MA region?

    Stockbridge has some great breakfast spots. The Red Lion Inn is a classic choice, known for its hearty breakfasts. The Allium Restaurant offers a more modern take on breakfast, with fresh and seasonal ingredients. And for a quick and delicious bite, try the Stockbridge Coffee & Tea, a local favourite for coffee and pastries.
  • What are the best bed and breakfasts with parking in Stockbridge, MA?

Popular destinations

Best Stockbridge, MA bed and breakfasts with parking

The Cornell Inn, Lenox & The Berkshires - Stockbridge, MA
No reviews

The Cornell Inn, Lenox & The Berkshires

B&B, Lenox
The Cornell Inn is a charming bed and breakfast situated in Lenox, just a short walk from the town centre and close to attractions like The Bookstore, Lenox Library, and Ventfort Hall Mansion. It enjoys a peaceful location, ideal for exploring the area's history and culture.
The inn offers a range of rooms, all equipped with modern amenities, including a microwave oven, air conditioning, and a private bathroom. Guests can enjoy a range of facilities, including a restaurant, a bar, a terrace, a garden, and free parking.
Queensboro - Pets Allowed-suite-salle De Bain Priv - Stockbridge, MA
9.5 4 reviews

Queensboro - Pets Allowed-suite-salle De Bain Priv

B&B, West Stockbridge
The Shaker Mill Inn, a pet-friendly guesthouse in West Stockbridge, Massachusetts, offers easy access to Berkshire attractions.
This ground-floor lodging boasts a private entrance, patio, two queen beds, a sofa bed sleeping up to four guests, and a fully equipped kitchen, plus the option of connecting to an adjacent room.
New England History | Bike-friendly. Dine + Pool - Stockbridge, MA
No reviews

New England History | Bike-friendly. Dine + Pool

B&B, Stockbridge
This guest house is located in the centre of Stockbridge, a short walk from shops and cultural attractions, and 3 kilometres from the Norman Rockwell Museum.
The property offers a heated outdoor pool, hot tub, fitness centre, complimentary bike rentals, and four on-site dining options, with accommodation for up to four guests in one bedroom.
Romantic! Fireplace, Jacuzzi & Private Entrance - Stockbridge, MA
9.4 79 reviews

Romantic! Fireplace, Jacuzzi & Private Entrance

B&B, Lenox
The Hampton Terrace Inn is situated in Lenox, Massachusetts, just a short drive from Tanglewood Musical Center and within 5 miles of the Bousquet Ski Area. This 4-star bed and breakfast consistently receives excellent user ratings for its location, cleanliness, and overall experience.
Each room in this charming inn is uniquely styled with antique furnishings and plush bedding. Guests can enjoy a delicious gourmet breakfast, relax by the outdoor pool, play tennis on the on-site courts, and take advantage of the spa, concierge service, and other amenities.

Best Stockbridge, MA bed and breakfasts with air conditioning

Cozy Carriage House Room With A Double Bed And Private Balcony - Stockbridge, MA
No reviews

Cozy Carriage House Room With A Double Bed And Private Balcony

B&B, Lenox
This Lenox, Massachusetts guesthouse is conveniently located near Kennedy Park (3.2km), Stockbridge Bowl (11.3km), and within a 2km walking distance of The Bookstore and Lenox Library.
The 11-square-metre (118 sq ft) self-catering unit offers one bedroom, one bathroom, sleeping up to three guests, and includes a coffee maker, kettle, and air conditioning; Bousquet Ski Area and Hotchkiss Mobile Studio are also nearby.
Brook Farm Inn - Stockbridge, MA
9.4 230 reviews

Brook Farm Inn

B&B, Lenox
The Brook Farm Inn is situated in the Berkshire Mountains, just seven miles from the Norman Rockwell Museum and eight miles from the Barrington Stage Company, offering easy access to cultural attractions. This highly rated guesthouse boasts excellent user, location, and cleanliness scores.
The inn features a range of comfortable rooms with private bathrooms, each decorated with unique style. Guests can enjoy a relaxing swim in the outdoor pool, explore the lush gardens, or unwind in the charming common areas, all while benefiting from complimentary Wi-Fi and a delicious breakfast buffet.
Tanglewood - Pets Allowed-suite-supérieure-salle D - Stockbridge, MA
9.3 3 reviews

Tanglewood - Pets Allowed-suite-supérieure-salle D

B&B, West Stockbridge
This B&B in West Stockbridge, located within the scenic Berkshires, offers a tranquil retreat with a private entrance and patio, providing easy access to local cultural and natural attractions. This family and pet-friendly guesthouse accommodates up to two guests in a ground-floor room featuring a queen bed, a kitchenette with a fridge and microwave, air conditioning, free Wi-Fi, and a complimentary continental breakfast served in-room.
Steps From Stockbridge Main Street | Dining & Pool - Stockbridge, MA
10 1 review

Steps From Stockbridge Main Street | Dining & Pool

B&B, Stockbridge
This B&B is located in downtown Stockbridge, within walking distance of shops and galleries, and 2 kilometres from the Norman Rockwell Museum.
Guests can enjoy complimentary bike rentals, live music at The Lion's Den, four on-site dining options, a year-round heated outdoor pool, a hot tub, and a fitness centre, with rooms accommodating up to two guests.
©2026 cozycozy.com