Search accommodations in Stockbridge, MA

137 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • makemytrip
  • oyo
  • yatra
  • goibibo
  • travelguru
  • cleartrip
  • vrbo
  • expedia
  • hotelscom
  • tripcom
  • agoda
Stockbridge, MA place to stay
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

137 Lodgings in Stockbridge, MA

Best family friendly Stockbridge, MA lodging

Among the 137 accommodations in Stockbridge, MA, here are the 4 best for families

Stylish Mid-century Modern Berkshires Cape - Stockbridge, MA
9.9 142 reviews
Stockbridge, MA
14/10 – 21/10
₹51334/nighttotal: ₹359338 (7 )

Stylish Mid-century Modern Berkshires Cape

1 4
apartment , Lee
This house is located on a lake in Lee, within 2 kilometres of Greenock Country Club, Lee Library, and Animagic Museum of Animation, offering a peaceful retreat in a convenient location. The property has received excellent ratings for user experience, location, and cleanliness.
The property has 4 bedrooms and can accommodate up to 8 guests, providing ample space for families or groups. It features a fully equipped kitchen, a terrace, a garden, and a washing machine, along with air conditioning, internet access, and a Smart TV for entertainment.
Rabbit Run In The Heart Of Stockbridge Village - Stockbridge, MA
9.8 116 reviews
Stockbridge, MA
14/10 – 21/10
₹37759/nighttotal: ₹264313 (7 )

Rabbit Run In The Heart Of Stockbridge Village

3 4
apartment , Stockbridge
This charming cottage is located in Stockbridge, just a short walk from the Red Lion Inn and within a 5-minute walk of hiking trails, a park, and tennis courts, offering easy access to both nature and entertainment. The property has received excellent ratings for location, cleanliness, and overall user experience.
The cottage has three bedrooms and two bathrooms, comfortably accommodating up to eight guests. Enjoy the modern kitchen, high-speed internet, comfortable beds, and a sleeper couch, along with a beautiful fenced-in backyard with mountain views, a deck, grill, and fire pit.
Classic Stockbridge Cottage - Stockbridge, MA
10 17 reviews
Stockbridge, MA
14/10 – 21/10
₹49558/nighttotal: ₹346906 (7 )

Classic Stockbridge Cottage

4 4
apartment , Stockbridge
This charming cottage is located in a quiet neighbourhood in Stockbridge, just a short walk from Chesterwood and the Rockwell Museum, and a short drive to Tanglewood, Berkshire Botanical Garden, and Stockbridge Bowl. The cottage has received excellent reviews from previous guests.
The property has four bedrooms and three bathrooms across 257 square metres, comfortably accommodating up to eight guests. This charming retreat features a well-equipped kitchen, a spacious living room with a fireplace, a library, a dedicated lounge area, and a private garden.
The Ponds At Foxhollow - Stockbridge, MA
8.4 316 reviews
Stockbridge, MA
14/10 – 21/10
₹29021/nighttotal: ₹203147 (7 )

The Ponds At Foxhollow

2 4
resort , Lee
The Ponds at Foxhollow by Capital Vacations is located in Lenox, Massachusetts, just a short drive from Tanglewood and the Tanglewood Musical Center, making it a great choice for music lovers and those looking to explore the scenic Berkshires. The resort enjoys excellent location and cleanliness ratings, with guests consistently praising its comfortable and well-maintained accommodation.
Each apartment features a fully equipped kitchen and a dining and seating area with a TV, providing everything you need for a relaxing stay. Guests can enjoy a range of amenities, including a seasonal outdoor pool and hot tub, an indoor pool, sauna, fitness center, and tennis court, as well as free bicycle use, fishing, and canoeing opportunities.

Best Stockbridge, MA lodging with a pool

Among the 137 accommodations in Stockbridge, MA, here are the 3 best ones with a pool

The Summerwood Hideout | Mins To Downtown! • Pool - Stockbridge, MA
9.6 11 reviews
Stockbridge, MA
14/10 – 21/10
₹63678/nighttotal: ₹445746 (7 )

The Summerwood Hideout | Mins To Downtown! • Pool

4 4
apartment , Great Barrington
Long Pond Luxe is a four-bedroom, four-bathroom property near Great Barrington town centre in the Berkshires, offering a secluded wooded setting.
This recently renovated holiday home, sleeping eight, boasts a private pool, patio, and a separate guest pool house; it includes a fully equipped kitchen with dishwasher and is conveniently located for exploring local shops, restaurants, and Berkshire attractions.
Tranquil Lakeside Escape In The Berkshires - Stockbridge, MA
9.2 19 reviews
Stockbridge, MA
30/08 – 08/09
₹31539/nighttotal: ₹283851 (9 )

Tranquil Lakeside Escape In The Berkshires

2 3
apartment , Lee
This apartment is located in The Ponds at Foxhollow Resort in Lee, Massachusetts, just a short drive (around 10 kilometres) from Lenox and the Tanglewood Music Center. The surrounding area is known for its picturesque scenery, offering stunning views of a pond and the Berkshire mountains.
The apartment has a master bedroom with a king-sized bed, a master bathroom with a jacuzzi, a fully equipped kitchen, a dining area, a living space with a double sleeper sofa, and a loft sitting room, comfortably accommodating up to six guests. Guests have access to a wide range of amenities, including swimming pools, a hot tub, a sauna, an exercise room, a library, and a business centre, as well as outdoor activities such as tennis courts, a putting green, and hiking trails.
The Summerwood Hideout | Mins To Downtown!  Pool - Stockbridge, MA
8.8 3 reviews
Stockbridge, MA
14/10 – 21/10
₹65100/nighttotal: ₹455700 (7 )

The Summerwood Hideout | Mins To Downtown! Pool

4 4
apartment , Great Barrington
This four-bedroom, four-bathroom Great Barrington holiday home is situated in a rural location, approximately 5km from Mansfield Lake Park and 4km from the Housatonic River.
The property, sleeping eight guests, boasts a private pool, tranquil balcony, fully equipped kitchen, in-unit laundry, Wi-Fi, and a fireplace, plus outdoor amenities including a fire pit and barbecue grill; nearby attractions include Ski Butternut, Greenock Country Club, Berkshire Botanical Garden, and Hoffman's Pottery.

Frequently asked questions about accommodations in Stockbridge, MA

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

    Stockbridge is a nature lover's paradise. You can hike or bike the scenic Appalachian Trail, explore the beautiful grounds of the Naumkeag estate, or go for a swim in Lake Buel. In the autumn, the foliage is spectacular, and you can enjoy a scenic drive along the Mohawk Trail.
  • When is the ideal time to plan a trip to Stockbridge, MA?

    The best time to visit Stockbridge is during the summer or autumn. The weather is pleasant, and there are plenty of outdoor activities to enjoy. If you're a fan of fall foliage, the autumn is especially beautiful. Spring and winter are quieter, and you might find some good deals on accommodation.
  • What are the best walking or cycling routes in Stockbridge, MA?

    The Stockbridge Town Common is a great place to start a walk or bike ride. You can explore the charming streets of the village and enjoy the beautiful scenery. The Stockbridge Bowl is another lovely spot for a walk or bike ride, offering scenic views of the lake and surrounding hills. For more challenging routes, check out the trails at the Hopkins Memorial Forest.
  • What nearby towns or cities can be explored from Stockbridge, MA?

    You can easily explore nearby towns like Lenox, Great Barrington, and Lee, all within a short drive. Lenox is known for its beautiful scenery and art galleries, while Great Barrington offers a lively downtown area with shops and restaurants. Lee is a charming town with a historic village centre.
  • What amenities can travelers expect from accommodations in Stockbridge, MA?

    Stockbridge offers a variety of accommodation options, from cozy bed and breakfasts to luxurious hotels. Many accommodations offer amenities like swimming pools, fitness centres, and restaurants. Some also have unique features like fireplaces, private balconies, or scenic views. You'll find something to suit every taste and budget.

Destinations nearby

Best Stockbridge, MA accommodations with a garden

Stylish Berkshires Retreat - Stockbridge, MA
10 6 reviews
Stockbridge, MA
14/10 – 21/10
₹23460/nighttotal: ₹164220 (7 )

Stylish Berkshires Retreat

1 4
apartment , Lee
This recently renovated two-bedroom flat in Lee offers convenient access to Tanglewood and the Berkshire Theatre Festival, situated just a short drive from Lee Premium Outlets and numerous ski resorts.
This well-appointed property accommodates up to four guests, featuring a fully equipped kitchen, air conditioning, and private parking, with direct access to Sandy Beach at Lake Laurel only 3 minutes away by car.
Hearth House • Prime Location! - Stockbridge, MA
8.0 2 reviews
Stockbridge, MA
14/10 – 21/10
₹40172/nighttotal: ₹281204 (7 )

Hearth House • Prime Location!

1 4
apartment , Stockbridge
This three-bedroom flat is situated in Stockbridge, a mere 1.2 kilometres from the Norman Rockwell Museum and Tanglewood, offering convenient access to Main Street and local shops.
The property accommodates up to six guests, featuring a fully equipped kitchen, air conditioning, Wi-Fi, a sauna, and parking, with a patio and garden for outdoor enjoyment and close proximity to hiking trails.
Hearth House | Prime Location! - Stockbridge, MA
Stockbridge, MA
14/10 – 21/10
₹42044/nighttotal: ₹294308 (7 )

Hearth House | Prime Location!

2 4
apartment , Stockbridge
This Stockbridge flat is located moments from the Norman Rockwell Museum and Tanglewood, offering easy access to local points of interest and natural landscapes, with the Berkshire Botanical Garden a mere 200 meters away.
This spacious 218 square meter residence features 3 bedrooms and 2.5 bathrooms, accommodating up to 6 guests with amenities including Wi-Fi, air conditioning, a garden, sauna, and parking.
The Hideaway On Main - Stockbridge, MA
10 6 reviews
Stockbridge, MA
14/10 – 21/10
₹35505/nighttotal: ₹248535 (7 )

The Hideaway On Main

1 4
apartment , Stockbridge
This Stockbridge cottage-style apartment is centrally located, steps from the town centre and its shops, restaurants and galleries.
The two-bedroom, one-bathroom flat sleeps four guests and features a fully equipped kitchen with high-end appliances, a private rear deck with gas grill, and a dedicated parking space.

Best Stockbridge, MA accommodations with a kitchen

Stockbridge Home: Walk To Town Beach! - Stockbridge, MA
9.8 50 reviews
Stockbridge, MA
14/10 – 21/10
₹32490/nighttotal: ₹227430 (7 )

Stockbridge Home: Walk To Town Beach!

3 4
house , Stockbridge
This Stockbridge house is located just 3.4 kilometres from Tanglewood, a renowned music venue, and 3.8 kilometres from the town beach, offering a peaceful setting close to cultural and natural attractions. The property has consistently received excellent ratings for location, cleanliness, and user experience.
The three-bedroom house spans 97 square metres and comfortably accommodates up to six guests. Amenities include a fully equipped kitchen, air conditioning, a terrace, a spa, parking, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
Stockbridge Village Cottage With Mountain Views And Walk To Town - Stockbridge, MA
9.8 63 reviews
Stockbridge, MA
14/10 – 21/10
₹43865/nighttotal: ₹307055 (7 )

Stockbridge Village Cottage With Mountain Views And Walk To Town

3 4
apartment , Stockbridge
This charming cottage is situated in the quintessential Berkshire village of Stockbridge, just a short walk from the Red Lion Inn and within a 5-minute walk of hiking trails, a park, and tennis courts. The property has received excellent user ratings, making it a popular choice for travellers seeking a comfortable and convenient stay.
This 158 square metre property has three bedrooms, two bathrooms, and can accommodate up to eight guests. The cottage features a well-equipped kitchen, a comfortable living area, a fenced-in backyard with mountain views, and a range of amenities including a foosball table, dart board, yoga mats, a Weber grill, a Solo firepit, and lake rights to the Stockbridge Bowl.
Renovated Colonial On The River! Fantastic Views - Stockbridge, MA
10 77 reviews
Stockbridge, MA
14/10 – 21/10
₹45879/nighttotal: ₹321153 (7 )

Renovated Colonial On The River! Fantastic Views

1 4
apartment , Stockbridge
This renovated 1820s colonial house in Stockbridge, Massachusetts, enjoys a picturesque location on the Housatonic River, offering stunning river and wildlife views and proximity to Stockbridge Bowl (distance to be clarified).
The 102-square-metre (1100 sq ft) property boasts three bedrooms, two bathrooms, a well-equipped kitchen, a three-season porch, and off-street parking for 2-4 cars, ideal for families seeking a relaxing Stockbridge getaway with spa facilities.
Cozy Stockbridge Cabin - Walk To Beach & Lake! - Stockbridge, MA
9.2 12 reviews
Stockbridge, MA
14/10 – 21/10
₹28466/nighttotal: ₹199262 (7 )

Cozy Stockbridge Cabin - Walk To Beach & Lake!

2 4
cabin , Stockbridge
This charming cottage is just over 5km from Tanglewood, the Norman Rockwell Museum, and Tanglewood, offering easy access to Stockbridge's cultural attractions. The accommodation has received excellent ratings for its location, cleanliness, and overall experience.
The 65 square metre cottage has two bedrooms and can accommodate up to four guests. It offers a fully equipped kitchen, air conditioning, a garden, a spa, free Wi-Fi, and parking, as well as stunning sea views and access to the beach and lake.
©2026 cozycozy.com