Places to stay in Stockbridge, MA

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Stockbridge, MA place to stay
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228 Best places to stay in Stockbridge, MA

Best family friendly Stockbridge, MA lodging

Among the 228 accommodations in Stockbridge, MA, here are the 4 best for families

Idyllic Retreat; Hot Tub/sauna By Evergreen Home - Stockbridge, MA
10 6 reviews

Idyllic Retreat; Hot Tub/sauna By Evergreen Home

apartment, Great Barrington
This spacious apartment is located in a rural setting, just 8 kilometres from Mansfield Lake Park and 7 kilometres from the Housatonic River. The surrounding area offers a peaceful and tranquil atmosphere, perfect for a relaxing getaway.
The apartment spans 227 square metres and comfortably accommodates up to 8 guests. It features a fully equipped kitchen, a private patio, a hot tub, and a fenced yard, making it ideal for families and groups.
Fall Foliage @ The Barrington House: Gb - Stockbridge, MA
10 11 reviews

Fall Foliage @ The Barrington House: Gb

apartment, Great Barrington
This three-bedroom, three-bathroom house near Great Barrington offers a private pool, lush gardens with a vegetable patch, and is within 16km of Lake Mansfield Beach, 24km from Lenox/Tanglewood, and 8km from Stockbridge.
Sleeping up to six adults, the property boasts a fully equipped kitchen, air conditioning, a fitness centre, and secure access; children's amenities are provided.
Hip Stockbridge Cabin - A Stroll To The Lake - Stockbridge, MA
9.8 260 reviews

Hip Stockbridge Cabin - A Stroll To The Lake

cabin, Stockbridge
This charming cottage is located in a peaceful lake neighbourhood in Stockbridge, just 1.6 kilometres from the public beach at Stockbridge Bowl. It has received excellent ratings for its location, cleanliness, and overall experience.
The 84 square metre cottage comfortably sleeps six guests and features a spacious outdoor area with a sunny deck, a charming fieldstone fireplace, and a dedicated reading nook. Enjoy the modern amenities including a fully equipped kitchen, air conditioning, a Jacuzzi, a garden, a spa, and parking.
Berkshires Forest Retreat With Hot Tub - Stockbridge, MA
10 83 reviews

Berkshires Forest Retreat With Hot Tub

apartment, Stockbridge
This apartment is located in Stockbridge, just 6 kilometres from Tanglewood and Lenox, offering a peaceful retreat in the picturesque Berkshires. With excellent user, location, and cleanliness ratings, this property promises a comfortable and enjoyable stay.
The apartment is a spacious home with 3 bedrooms and 2 bathrooms, comfortably accommodating up to 7 guests. The property features a fully equipped kitchen, a dedicated office space, a large outdoor deck, a hot tub, a fire pit, a swingset, and a washer and dryer, ensuring a relaxing and enjoyable experience for all.

Best Stockbridge, MA lodgings with a pool

Among the 228 accommodations in Stockbridge, MA, here are the 4 best ones with a pool

Stunning Luxury Home With Pool - Stockbridge, MA
10 92 reviews

Stunning Luxury Home With Pool

apartment, Great Barrington
This four-bedroom home is located in Great Barrington, just 10-15 minutes' drive from the town centre, shops, restaurants, skiing, and Tanglewood, with Monument Mountain on your doorstep. The property has excellent ratings for location, cleanliness, and user experience.
The spacious apartment can accommodate up to eight guests and comes equipped with a gourmet kitchen, a grand piano, a state-of-the-art gym, a private swimming pool, and a large three-season porch overlooking the pool and patio. Enjoy complimentary gourmet coffee, high-speed Wi-Fi, central heating and air conditioning, a Tesla EV charger, and a Wi-Fi-enabled garage door system.
The Ponds At Foxhollow - Stockbridge, MA
8.2 323 reviews

The Ponds At Foxhollow

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.
Villa With Access To Various Amenities - Stockbridge, MA
9.3 38 reviews

Villa With Access To Various Amenities

house, Lee
This charming property is situated in the central Berkshires, just an 11-minute drive from the Norman Rockwell Museum, offering a peaceful retreat in a picturesque setting. The house has received excellent ratings for its location, cleanliness, and overall user experience.
The property is a one-bedroom dwelling with one bathroom, comfortably accommodating up to four guests. Amenities include a swimming pool, jacuzzi, sauna, fitness centre, and free parking, allowing for a relaxing and enjoyable stay.
Tranquil Lakeside Escape In The Berkshires - Stockbridge, MA
10 1 review

Tranquil Lakeside Escape In The Berkshires

apartment, Lenox
This Lenox condo, a short 6.4km drive from The Mount and 9.6km from the Housatonic River, offers convenient access to local attractions.
The two-bedroom, three-bathroom apartment sleeps six, boasting a fully equipped kitchen, in-unit laundry, a swimming pool, sauna, parking, and free Wi-Fi.

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Best Stockbridge, MA accommodations with a garden

Historical Housatonic Street Building - Stockbridge, MA
10 25 reviews

Historical Housatonic Street Building

apartment, Lenox
This two-bedroom flat in Lenox offers convenient access, situated a short drive from Tanglewood and within walking distance of the Lenox Library, local shops, and restaurants.
This accommodation provides a comfortable stay for two guests, featuring air conditioning, a kitchen with a fridge, microwave, and dishwasher, plus on-site parking and a garden.
Hearth House | Prime Location! - Stockbridge, MA
No reviews

Hearth House | Prime Location!

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 Taggart House - Stockbridge, MA
9.8 163 reviews

The Taggart House

house, Stockbridge
This beautiful six-bedroom house is located in Stockbridge, just a short distance from Mission House, a significant historical site, and within a 24-kilometre drive of Schantz Galleries and the Berkshire Theatre Festival. This property has consistently received excellent ratings for its location, cleanliness, and overall experience.
This spacious home provides ample room for a large family or group of friends, covering 836 square metres and comfortably accommodating up to 12 guests. The house offers a range of modern amenities, including a fully equipped kitchen, a spa, a tennis court, and a beautiful garden with a barbecue, perfect for enjoying the outdoors.
General Williams Estate House Lenox/stockbridge - Stockbridge, MA
9.8 117 reviews

General Williams Estate House Lenox/stockbridge

apartment, Stockbridge
This spacious six-bedroom house, known as the General Williams house, is situated in Berkshire County, Massachusetts, 3.2km from Stockbridge centre and 8km from Lenox centre, offering easy access to the Mass Pike.
The 511-square-metre property boasts two fully equipped kitchens, six fireplaces, a games room, a swimming pool, and a spa, accommodating up to 16 guests and providing ample space for families or large groups.

Best Stockbridge, MA accommodations with a kitchen

Berkshire House Stay-5bed/5bath-summer-fun - Stockbridge, MA
10 72 reviews

Berkshire House Stay-5bed/5bath-summer-fun

apartment, Lee
This five-bedroom, five-bathroom house in Lee, Massachusetts, is ideally located near the town centre, the weekly farmers' market, Starving Artist Cafe, and Greenock Country Club, with Stockbridge a short 8km drive away.
The spacious property, sleeping up to 10 guests, boasts a fully equipped kitchen with dishwasher, a garden with BBQ and firepit, plus free access to the Lee Trolley (seasonal) and 24-hour security.
Justice's Birthplace: King Bed, Hearths, Gardens - Stockbridge, MA
9.7 84 reviews

Justice's Birthplace: King Bed, Hearths, Gardens

house, Lee
This charming house in Stockbridge is just a short drive from Lee Premium Outlets, Lenox Center, and Canyon Ranch, placing you near a range of attractions and shopping opportunities. The house has consistently received excellent ratings for its cleanliness, location, and overall guest experience.
The property offers a private entrance and separate living space for up to four guests. It features a fully equipped kitchen, modern appliances, a private porch, and a garden, making it a comfortable and convenient option for your stay.
Spacious 3 Bedroom Apt In Lenox Historic Downtown - Stockbridge, MA
9.8 50 reviews

Spacious 3 Bedroom Apt In Lenox Historic Downtown

apartment, Lenox
This newly renovated three-bedroom apartment is centrally located in downtown Lenox, Massachusetts, a 2.4km walk from Tanglewood, the summer home of the Boston Symphony Orchestra, and within walking distance of numerous restaurants and shops.
The 3-bedroom, 2-bathroom flat offers free on-site parking, a fully equipped kitchen including a dishwasher, air conditioning, and a garden; it comfortably sleeps six guests.
Greenhouse - Stockbridge, MA
10 131 reviews

Greenhouse

apartment, Lee
The GreenHouse guest cottage is situated on the grounds of the historic Hyde House in Lee, Massachusetts, within walking distance of Lee's town centre and a short drive from Stockbridge and Lenox.
This self-contained cottage sleeps four guests in two bedrooms and one bathroom, boasting a kitchen with fridge, freezer and microwave, air conditioning, parking, and excellent guest reviews; nearby attractions include hiking trails and the Berkshires' scenic drives.
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