Bed and Breakfast and Inn in Stockbridge, MA

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Stockbridge, MA B&B
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37 Bed and Breakfasts and Inn in Stockbridge, MA

Best Stockbridge, MA bed and breakfasts with breakfast included

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.
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.
Brook Farm Inn - Stockbridge, MA
9.4 232 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.
Whistler's Inn - Stockbridge, MA
8.0 666 reviews

Whistler's Inn

B&B, Lenox
The Whistler's Inn is a charming bed and breakfast situated in Lenox, Massachusetts, a short distance from Tanglewood Musical Center and Shakespeare & Company Theater. The inn has consistently received very good user ratings for its cleanliness and excellent location.
Each room at the inn has a unique style and features a private bathroom. Guests can enjoy a daily gourmet breakfast, afternoon tea and cookies, and have access to a parlour room with a piano and a library. The inn also has a garden and a terrace, and guests can enjoy free Wi-Fi and parking.

Best Stockbridge, MA bed and breakfasts with a garden

Whistler's Inn/the Cotswolds Room (#2) - Stockbridge, MA
9.6 86 reviews

Whistler's Inn/the Cotswolds Room (#2)

B&B, Lenox
Whistler's Inn is a charming historic house in Lenox, just a short distance from Tanglewood, Shakespeare & Co., and other cultural attractions in the Berkshires. This B&B enjoys excellent ratings for its location, cleanliness and overall experience.
The house features a comfortable library with 2,000 books, a grand music room with a Steinway piano, and a peaceful terrace overlooking the gardens. Guests can enjoy a delicious breakfast with local ingredients, relax in the library with complimentary sherry or port, and explore the surrounding area.
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.
Standard Queen At Hideaway Inn Lenox - Stockbridge, MA
9.5 8 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.
Garden - Pets Allowed-suite-de Luxe-salle De Bain - Stockbridge, MA
10 6 reviews

Garden - Pets Allowed-suite-de Luxe-salle De Bain

B&B, West Stockbridge
The Shaker Mill Inn, a guest house in West Stockbridge, Massachusetts, offers a pet-friendly room with a private balcony overlooking a rock garden, conveniently located a short drive from the Berkshires' cultural attractions.
This self-catering property features a comfortable second-floor room with a private entrance, sleeping up to two guests, and includes a kitchen, air conditioning, parking, and Wi-Fi; a connecting room is available for larger families.

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

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.
Shaker Mill Inn - Stockbridge, MA
9.5 577 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.
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.
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.

Best Stockbridge, MA bed and breakfasts with air conditioning

Gateways Inn - Stockbridge, MA
8.1 220 reviews

Gateways Inn

B&B, Lenox
This historic 1912 guesthouse in Lenox is located 2.7 kilometres from Tanglewood and 6.7 kilometres from the Norman Rockwell Museum, with Cranwell Spa & Golf Club and Tanglewood Musical Centre both just 2.4 kilometres away.
Guests can enjoy amenities such as air conditioning, complimentary WiFi, private parking, a fridge in the room, and access to a spa, fitness centre, restaurant and bar.
Elegant Suite With A King Bed, Fireplace, And Kitchenette. - Stockbridge, MA
No reviews

Elegant Suite With A King Bed, Fireplace, And Kitchenette.

B&B, Lenox
This Lenox guesthouse is conveniently located within a 1.9km walk of both The Bookstore and Lenox Library.
The 20-square-metre property offers one bedroom, one bathroom, sleeps three guests, and includes a fully equipped kitchen with refrigerator and coffee maker.
Granville House - Stockbridge, MA
9.9 338 reviews

Granville House

B&B, Great Barrington
Granville House is a charming bed and breakfast located in Great Barrington, Massachusetts, just 10 kilometres from the Norman Rockwell Museum and 18 kilometres from the Tanglewood Musical Center. The property has received excellent ratings for its location, cleanliness and overall guest experience.
The inn offers one bedroom and one bathroom, providing a comfortable and cosy stay for travellers. Guests can enjoy a delicious American breakfast each morning, free parking, and access to a garden, internet, air conditioning, and a restaurant.
Historic Susan B. Anthony Room - Cozy & Charming Stay - Stockbridge, MA
No reviews

Historic Susan B. Anthony Room - Cozy & Charming Stay

B&B, Lenox
This Lenox guesthouse is situated a 1.9km walk from both The Bookstore and Lenox Library, offering easy access to Tanglewood Music Center and Ventfort Hall Mansion.
The 14-square-metre studio sleeps three, features a fireplace and air conditioning, and includes linens and heating.
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