Search accommodations in Stockbridge, MA

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Stockbridge, MA accommodations
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228 Lodgings in Stockbridge, MA

Discover Central Lodgings in Stockbridge, MA

Choosing central accommodation in downtown Stockbridge, MA maximizes your time, putting popular museums, historic districts, and local restaurants within walking distance.

Stockbridge Private Apartment - Stockbridge, MA
9.9 95 reviews

Stockbridge Private Apartment

apartment, Stockbridge
This Stockbridge apartment rental, located one mile from downtown Stockbridge and a 10-minute drive from Tanglewood, Stockbridge Bowl, and Kripalu Center for Yoga & Health, offers easy access to area attractions. This one-bedroom, one-bathroom unit sleeps four guests comfortably with two queen beds, a private entrance, a shared backyard with a fire pit, and on-site parking for two vehicles; note that there is train noise twice daily.
Historic,famous,iconic, Unforgettable Berks Escape - Stockbridge, MA
9.9 124 reviews

Historic,famous,iconic, Unforgettable Berks Escape

apartment, Stockbridge
This studio apartment is located in the heart of Stockbridge's historic downtown, just a short walk from the renowned Norman Rockwell Museum. It consistently receives excellent ratings for its location, cleanliness, and overall experience.
This cozy one-bedroom apartment can comfortably accommodate up to three guests. You’ll find a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher, along with air conditioning and parking. Enjoy the unique opportunity to stay in the very studio where Norman Rockwell worked for four years, complete with the original picture window offering stunning views of Main Street.
The Hideaway On Main - Stockbridge, MA
10 6 reviews

The Hideaway On Main

apartment, Stockbridge
This Stockbridge apartment rental is steps from the town center, offering easy access to local shops and attractions.
The two-bedroom, one-bathroom unit features a fully equipped kitchen with a Gaggia espresso machine, a private deck with a gas grill, and parking for two vehicles, comfortably accommodating up to four guests.
Too Good Aka 2 Goodrich St - Stockbridge, MA
9.9 166 reviews

Too Good Aka 2 Goodrich St

house, Stockbridge
"Too Good AKA 2 Goodrich St" is a charming house situated in Stockbridge, a short distance from both the Norman Rockwell Museum and the Tanglewood Music Center. This vacation home has consistently received excellent ratings for its cleanliness, location, and overall experience.
This 4-bedroom house offers 3,000 square feet of comfortable living space. You'll enjoy a fully equipped kitchen, a relaxing garden, and modern amenities like air conditioning, free Wi-Fi, and a dishwasher.

Choose the Right Family Lodgings in Stockbridge, MA

Discover kid-friendly lodgings in Stockbridge, MA that keep city attractions within easy reach, ensuring everyone stays comfortable.

Sun-filled, Charming Stockbridge Classic- In Town! - Stockbridge, MA
9.9 164 reviews

Sun-filled, Charming Stockbridge Classic- In Town!

apartment, Stockbridge
This Stockbridge apartment is located on a quiet dead-end road, just a short walk from the town center, the Red Lion Inn, and a park with hiking trails leading to Laura's Tower. The apartment boasts excellent user, location, and cleanliness ratings.
The apartment has two bedrooms and one bathroom, comfortably accommodating up to four guests. The apartment offers a fully equipped kitchen, a private fenced yard with a grill and screened-in porch, air conditioning, and internet access.
General Williams Estate House Lenox/stockbridge - Stockbridge, MA
9.8 120 reviews

General Williams Estate House Lenox/stockbridge

apartment, Stockbridge
This spacious Stockbridge estate, two miles from Stockbridge Center and five miles from Lenox Center, offers easy access to the Mass Pike and Berkshire attractions.
The 5,500-square-foot home boasts six bedrooms, six bathrooms, and accommodates up to sixteen guests, featuring two kitchens, a pool, a spa, and ample outdoor space perfect for family gatherings or group retreats.
Comfortable Elegance On Secluded Property In Lenox - Stockbridge, MA
10 96 reviews

Comfortable Elegance On Secluded Property In Lenox

apartment, Lenox
This five-bedroom home is located in Lenox, a short walk from the town center and two miles from Tanglewood, offering a peaceful retreat in a prime location. The apartment has received excellent ratings for user experience, location, and cleanliness.
This 2600 square foot home comfortably accommodates nine guests. Amenities include a fully equipped kitchen, a Jacuzzi, a garden, and parking, along with access to a spa and internet.
Stunning Post & Beam Home Minutes From Lenox, Stockbridge And Tanglewood! - Stockbridge, MA
10 99 reviews

Stunning Post & Beam Home Minutes From Lenox, Stockbridge And Tanglewood!

apartment, Lee
This vacation home in Lee is located close to a lake, within a mile of Greenock Country Club and the Housatonic River, offering a peaceful escape near local attractions. It has received excellent user ratings, making it a popular choice for travelers.
The home features five bedrooms, four bathrooms, and can comfortably accommodate up to 14 guests in its 2800 square feet of space. Amenities include a fully equipped kitchen, a fireplace, a fitness center, a spa, a garden, a terrace, and parking, ensuring a comfortable and enjoyable stay.

Frequently Asked Questions about accommodations in Stockbridge, MA

  • What are the must-see sites in or near Stockbridge, MA?

    You can't miss the Norman Rockwell Museum, which showcases his iconic American art. Take a stroll through the beautiful grounds of the Naumkeag estate, a Gilded Age mansion with stunning gardens. If you're a history buff, the Stockbridge Historical Society is a great place to learn about the town's past.
  • What are the best accommodations in Stockbridge, MA?

    Among the accommodations in Stockbridge, MA, The Red Lion Inn, A Grand Property In Historic Stockbridge and Tranquil 3 Br Stockbridge House With Private Deck are the most popular ones.

  • How can travelers reach Stockbridge, MA?

    The easiest way to get to Stockbridge is by car, as it's about a 2-hour drive from Boston or New York City. You can also take a train to the nearby town of Pittsfield and then take a bus or taxi to Stockbridge. There is a small airport in Pittsfield, but it doesn't have many commercial flights.
  • What are the best accommodations with a pool in Stockbridge, MA?

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

    Stockbridge is surrounded by beautiful scenery, perfect for hiking and biking. The Appalachian Trail runs right through town, and there are many other trails to explore in the nearby Berkshires. You can also go kayaking or canoeing on the Housatonic River, or visit the Hopkins Memorial Forest for a leisurely walk.
  • What are the best accommodations with a jacuzzi in Stockbridge, MA?

  • When is the ideal time to plan a trip to Stockbridge, MA?

    The best time to visit Stockbridge is during the fall, when the leaves change colors and the scenery is absolutely breathtaking. Spring and summer are also nice, with pleasant temperatures and plenty of outdoor activities to enjoy. Winter can be beautiful, too, with snow-covered landscapes, but be prepared for colder weather.
  • What are the best accommodations for families and kids in Stockbridge, MA?

    The best accommodations for families and kids in Stockbridge, MA are The Red Lion Inn, A Grand Property In Historic Stockbridge and Too Good Aka 2 Goodrich St.

  • What are the best walking or cycling routes in Stockbridge, MA?

    For a scenic walk, try the Stockbridge Bowl Loop Trail, which goes around the lake and offers views of the surrounding hills. For a longer bike ride, you can follow the Housatonic River Bike Path, which stretches for miles along the river.
  • What are the best pet friendly accommodations in Stockbridge, MA?

  • What nearby towns or cities can be explored from Stockbridge, MA?

    You can easily make day trips to nearby towns like Lenox, Great Barrington, and Pittsfield. Each of these towns has its own unique charm and attractions. You can also visit the city of Springfield, which is about an hour away and has several museums and historical sites.
  • What are the best accommodations with parking in Stockbridge, MA?

  • What amenities can travelers expect from accommodations in Stockbridge, MA?

    Stockbridge offers a variety of accommodations, from cozy bed and breakfasts to upscale hotels. Most places have comfortable rooms, some with fireplaces or private balconies. Many also offer amenities like swimming pools, hot tubs, and complimentary breakfast.

Popular destinations

Best Stockbridge, MA accommodation with a kitchen

Downtown Housatonic House 10 Miles To Tangelwood - Stockbridge, MA
9.8 10 reviews

Downtown Housatonic House 10 Miles To Tangelwood

apartment, Great Barrington
This 3-bedroom, 2-bathroom rental property is located in Housatonic village, 2 miles from downtown Great Barrington, 1 mile from the Norman Rockwell Museum, and 1 mile from the Botanical Garden.
This pet-friendly apartment accommodates up to 5 guests and features a full kitchen, air conditioning, internet, a front porch, and a private, fenced backyard.
Three Bedroom Duplex In Stockbridge On The River - Stockbridge, MA
10 53 reviews

Three Bedroom Duplex In Stockbridge On The River

apartment, Stockbridge
Riverside Haven is a three-bedroom apartment in Stockbridge, Massachusetts, situated on the picturesque Housatonic River, within walking distance of renowned music venues, museums, and restaurants. It has received excellent ratings for its location, cleanliness, and user experience.
The apartment has two floors, providing privacy for its six guests. It features a well-equipped kitchen, a private yard and riverfront with lounges, chairs, an umbrella, tables, and a gas grill, a primary bedroom with a connected office, shared laundry facilities, and a portable fire pit.
Renovated Historic Home In The Berkshires - Stockbridge, MA
10 72 reviews

Renovated Historic Home In The Berkshires

apartment, Stockbridge
This Stockbridge vacation home is situated within a 10-minute walk of the Housatonic River and Chesterwood, and within 2 miles of the Norman Rockwell Museum and Berkshire Botanical Garden. This two-bedroom house comfortably sleeps four guests and features a fully equipped kitchen, a private garden, and a patio with a barbecue grill.
Stockbridge Village Cottage With Mountain Views And Walk To Town - Stockbridge, MA
9.8 67 reviews

Stockbridge Village Cottage With Mountain Views And Walk To Town

apartment, Stockbridge
This Stockbridge apartment is in the heart of town, within walking distance of the Red Lion Inn and Norman Rockwell's home. It has an excellent user rating.
The apartment has 1700 square feet of space, 3 bedrooms, 2 bathrooms, and can accommodate up to 8 guests. It features a fully updated kitchen, hardwood floors, a foosball table, a dart board, and a fenced-in backyard with a Weber grill and Solo firepit.

Best Stockbridge, MA accommodation with parking

Classic Tanglewood Retreat - Stockbridge, MA
10 9 reviews

Classic Tanglewood Retreat

apartment, Stockbridge
This Stockbridge vacation home, minutes from Berkshire attractions like Tanglewood, offers easy access to skiing and shopping.
The three-bedroom, two-bathroom house, accommodating up to nine guests, features a fully equipped kitchen, air conditioning, parking, a separate cottage, and outdoor amenities including cornhole, a frisbee, and a yard swing on nearly four acres.
Cottage With Exquisite Views - Stockbridge, MA
9.9 23 reviews

Cottage With Exquisite Views

cottage, Stockbridge
This Stockbridge guest house sits on 116 acres of farmland in the Berkshires, minutes from Lenox and Great Barrington, providing easy access to Tanglewood and the Norman Rockwell Museum.
The three-bedroom, four-bathroom rental boasts a large kitchen, screened porch, fireplace, and accommodates up to seven guests, with nearby birdwatching and on-site assistance available.
Tranquil 3 Br Stockbridge House W/ Private Deck! - Stockbridge, MA
9.9 161 reviews

Tranquil 3 Br Stockbridge House W/ Private Deck!

house, Stockbridge
This Stockbridge home is located just 5.3 miles from Tanglewood Musical Center and 1.4 miles from the Norman Rockwell Museum, offering a peaceful escape while still being close to popular attractions. This vacation rental has consistently received excellent ratings for location, cleanliness, and overall experience.
The 3-bedroom house can comfortably accommodate up to 6 guests and provides 1600 square feet of space. Amenities include a fully equipped kitchen, air conditioning, a private deck, and free Wi-Fi, ensuring a comfortable and enjoyable stay.
Rustic Modern Retreat - Stockbridge, MA
9.8 72 reviews

Rustic Modern Retreat

apartment, West Stockbridge
This modern rustic cottage is situated just one mile from the center of West Stockbridge, providing easy access to the town's shops, restaurants, and attractions, as well as hiking trails, kayaking opportunities, and skiing in the winter. The three-bedroom, one-bathroom cottage features a spacious and airy interior, a large deck with a grill and fire pit, and a fully equipped kitchen with a refrigerator, freezer, microwave oven, and dishwasher, accommodating up to six guests.

Best Stockbridge, MA lodging with a pool

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

Peaceful 1br Condo With Pond View - Stockbridge, MA
8.0 2 reviews

Peaceful 1br Condo With Pond View

apartment, Lenox
Berkshires Mid-century Retreat! - Stockbridge, MA
No reviews

Berkshires Mid-century Retreat!

apartment, West Stockbridge
Historic Stockbridge Villa On 25 Acres - Stockbridge, MA
10 20 reviews

Historic Stockbridge Villa On 25 Acres

apartment, Stockbridge
Amore Estate -  Beautiful Room With Many Places To Explore And Relax In. - Stockbridge, MA
9.2 41 reviews

Amore Estate - Beautiful Room With Many Places To Explore And Relax In.

apartment, Lenox

Browse 5-Star Accommodations in Stockbridge, MA

Upscale lodgings in Stockbridge, MA offer the kind of stay you will want to return to, featuring premium amenities and refined service.

Light-filled Carpenter's Cottage - Stockbridge, MA
10 4 reviews

Light-filled Carpenter's Cottage

apartment, Stockbridge

Top-Rated Pet-Friendly Lodgings in Stockbridge, MA

Bringing your dog to Stockbridge, MA? Every lodging here is set up for pets, with dog parks nearby and city walks right on the doorstep.

Luxury Fox Hollow Estate Home On Laurel Lake - Dream Location, Hot Tub, Kayaks++ - Stockbridge, MA
9.2 67 reviews

Luxury Fox Hollow Estate Home On Laurel Lake - Dream Location, Hot Tub, Kayaks++

apartment, Lee
Cozy Riverside Berkshires Retreat - Stockbridge, MA
9.6 23 reviews

Cozy Riverside Berkshires Retreat

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

Spacious 4br Central-berkshires Home With Pool!

apartment, Lee
Classic Stockbridge Cottage - Stockbridge, MA
10 19 reviews

Classic Stockbridge Cottage

apartment, Stockbridge
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