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Stockbridge, MA place to stay
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228 Lodgings in Stockbridge, MA

Best family friendly Stockbridge, MA lodging

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

Family & Pet Friendly Home: Sunlit, Yard, Laundry - Stockbridge, MA
9.7 45 reviews

Family & Pet Friendly Home: Sunlit, Yard, Laundry

house, Lee
This charming Greek Revival farmhouse is located in Stockbridge, just a short distance from Lee Premium Outlets, Lenox, and cultural attractions like The Mount, the Norman Rockwell Museum, and Shakespeare & Co., offering a peaceful and picturesque setting. The property has received excellent ratings for user experience, location, and cleanliness.
This two-bedroom, two-bathroom apartment has a private entrance and can accommodate up to four guests. The property features a fully equipped kitchen, a private yard, a laundry room, and amenities like air conditioning, internet access, and parking.
Historic South Lee Apt 2 Mi To Main Street - Stockbridge, MA
No reviews

Historic South Lee Apt 2 Mi To Main Street

apartment, Lee
This South Lee flat provides easy access, situated a 5-minute walk from the Housatonic River and a 5-minute drive from Naumkeag Historic House.
This 139 square meter flat accommodates up to four guests with two bedrooms and one bathroom, featuring a fully equipped kitchen, air conditioning, on-site parking, and a fireplace for a comfortable stay.
Exceptional Stockbridge Retreat - Stockbridge, MA
10 22 reviews

Exceptional Stockbridge Retreat

apartment, Stockbridge
This Stockbridge apartment, near the Norman Rockwell Museum and Taglewood, offers easy access to Berkshire attractions.
Sleeping eight guests, the three-bedroom, one-bathroom property includes a kitchen with dishwasher, air conditioning, a garden, parking, and internet access.
The Cottage At The Barrington House - Stockbridge, MA
9.9 210 reviews

The Cottage At The Barrington House

apartment, Great Barrington
This Great Barrington cottage, near Monument Mountain, is conveniently located 5km from Stockbridge, 16km from Great Barrington town centre, and 24km from Lenox, offering easy access to the Berkshires' cultural attractions.
The self-catering property sleeps two comfortably (with an optional air mattress for four), features a modern design, a Breeo smokeless fire pit, and an indoor fireplace with firewood provided; owners are on-site.

Best Stockbridge, MA lodging with a pool

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

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.
Spacious 4br Central-berkshires Home With Pool! - Stockbridge, MA
10 3 reviews

Spacious 4br Central-berkshires Home With Pool!

apartment, Lee
This Lee holiday let is conveniently situated less than 1 kilometre from the Mass Pike exit, offering easy access to Lee Premium Outlets and recreational pursuits such as skiing, hiking, and golf at Greenock Country Club and Wyndhurst Golf & Club.
This 4-bedroom, 2-bathroom apartment accommodates up to 9 guests and features a well-equipped kitchen, outdoor grilling area, swimming pool, and garden, with well-behaved pets considered on a case-by-case basis.
Peaceful 1br Condo With Pond View - Stockbridge, MA
9.5 11 reviews

Peaceful 1br Condo With Pond View

apartment, Lee
This apartment is located in The Ponds at Foxhollow Resort in Lee, Massachusetts, just a short distance from the picturesque Berkshire Mountains. The resort is situated near a tranquil pond, offering scenic views and a peaceful atmosphere.
This comfortable apartment, suitable for up to four guests, features a master bedroom with a king-size bed, a master bathroom with a jacuzzi, a fully equipped kitchen, a dining area, and a living area with a double sleeper sofa. The apartment benefits from a range of amenities including a swimming pool, jacuzzi, sauna, fitness centre, and free Wi-Fi, alongside a variety of activities such as tennis courts, a putting green, and access to bicycles for exploring the surrounding area.
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.

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.

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Best Stockbridge, MA accommodations with a garden

Cozy Summer Haven! - Stockbridge, MA
10 12 reviews

Cozy Summer Haven!

house, Stockbridge
This Stockbridge guest house, in the Berkshires of Western Massachusetts, offers easy access to major attractions, though precise distances aren't specified.
The self-catering cottage sleeps four (two adults, two children) and boasts a private garden with playhouse, parking, and amenities including a fridge, freezer, microwave, and air conditioning.
Hideaway In The Woods - Stockbridge, MA
9.8 28 reviews

Hideaway In The Woods

apartment, Stockbridge
This three-storey cabin, near Great Barrington, West Stockbridge, and Lenox, offers a secluded cul-de-sac location with waterfall views and is approximately 3.2km from Tanglewood and Kripalu.
The property features an open-loft design, sleeps up to six guests in three bedrooms and one bathroom, includes a well-equipped kitchen, a hot tub (available April-December), and provides Wi-Fi, parking, and accepts pets.
Elegant Year-round Lakeside Retreat With Ac - Stockbridge, MA
9.9 193 reviews

Elegant Year-round Lakeside Retreat With Ac

apartment, Great Barrington
This elegant cottage is situated on a pristine lake in the Berkshires, just 10km from the market town of Great Barrington.
The four-bedroom property offers guests access to a 60-acre private lake with a dock, kayaks, a paddle board, and a fire pit, and can accommodate up to eight guests.
Secluded Chic Mountain Chalet Near Tanglewood - Stockbridge, MA
9.9 57 reviews

Secluded Chic Mountain Chalet Near Tanglewood

apartment, West Stockbridge
This contemporary chalet is located just 7 kilometres from the world-renowned Tanglewood music venue and 1.6 kilometres from the charming town of West Stockbridge, offering a tranquil escape amidst the natural beauty of the Berkshires. The property has received excellent ratings for location, cleanliness, and overall user experience.
The chalet has three bedrooms and two bathrooms, comfortably accommodating up to six guests. This modern retreat features a spacious open floor plan, a fully equipped kitchen, a large den, a private deck, and a laundry room with washer and dryer, providing all the comforts of home for a relaxing and enjoyable stay.

Best Stockbridge, MA accommodations with a kitchen

Rabbit Run In The Heart Of Stockbridge Village - Stockbridge, MA
9.8 124 reviews

Rabbit Run In The Heart Of Stockbridge Village

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.
Hearth House  Prime Location! - Stockbridge, MA
9.3 6 reviews

Hearth House Prime Location!

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.
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.
Historic Family Retreat On The At & Housatonic! - Stockbridge, MA
No reviews

Historic Family Retreat On The At & Housatonic!

apartment, Lee
This historic farmhouse, built in 1815 and listed on the National Register of Historic Places, is located in South Lee, 3 kilometres from downtown Lee and 3.2 kilometres from Stockbridge, offering mountain and river views from its shared yard and convenient access to Ski Butternut (16 kilometres), Bousquet Mountain (19 kilometres), October Mountain State Forest (9.7 kilometres), and the Appalachian Trail.
This 139 square metre residence provides 3 bedrooms and 2 bathrooms accommodating up to 5 guests, with features including a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, free WiFi, a washer/dryer, and keyless entry, while being family-friendly and pet-friendly for an additional fee.
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