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.

Hearth House | Prime Location! - Stockbridge, MA
10 1 review

Hearth House | Prime Location!

apartment, Stockbridge
This Stockbridge apartment is located minutes from the Norman Rockwell Museum and Tanglewood, offering convenient access to local attractions.
This 2350 square foot residence features 2 bedrooms and 2 bathrooms, accommodating up to 6 guests with a fold-out sofa, and includes a full kitchen, yard with patio, Wi-Fi, air conditioning, and parking.
Stockbridge Escape - Stockbridge, MA
10 6 reviews

Stockbridge Escape

apartment, Stockbridge
This newly renovated main floor apartment is located a block from Main Street in Stockbridge, placing you within easy walking distance of its shops and galleries.
The apartment accommodates up to four guests with one king and one queen bed, featuring a private back deck with a fire pit, a fenced backyard with a dog door, and a tiled bathroom with a steam shower.
Hearth House  Prime Location! - Stockbridge, MA
9.4 7 reviews

Hearth House Prime Location!

apartment, Stockbridge
This Stockbridge apartment is located a short drive from the Norman Rockwell Museum, Tanglewood, and Main Street.
This 3-bedroom, 2.5-bathroom rental accommodates up to 6 guests and features a fully equipped kitchen, air conditioning, sauna, and parking, with an outdoor yard and patio for relaxation.
The Taggart House - Stockbridge, MA
9.8 163 reviews

The Taggart House

house, Stockbridge
This family-friendly vacation home is located in Stockbridge, just steps from the Housatonic River and Mission House, with Schantz Galleries and the Berkshire Theatre Festival within a 15-minute drive. The property has received excellent ratings for its cleanliness, location, and overall experience.
The 9,000 square foot house has 6 bedrooms and can comfortably accommodate up to 12 guests. It features a fully equipped kitchen, a spacious living area, a private patio, a garden, a spa, a tennis court, and direct access to the Housatonic River for swimming, kayaking, and fishing.

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.

New England Family Retreat In Stockbridge, Ma - Stockbridge, MA
9.7 89 reviews

New England Family Retreat In Stockbridge, Ma

apartment, Stockbridge
This Stockbridge home, a short walk from Main Street and the Red Lion Inn, offers easy access to Laurel Hill trails and is six miles from Butternut Basin ski area.
The four-bedroom, three-bathroom house sleeps six, features a modern kitchen, Ipe wood patio with BBQ, a sauna, fitness center, and family-friendly amenities including a high chair and crib, all within a quiet setting near nature trails.
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.
Condo ∙ 2 Bedrooms ∙ 6 Guests - Stockbridge, MA
No reviews

Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Lenox
This Lenox, Massachusetts condo rental is conveniently located in the Berkshires, a short drive from The Mount (2.9 miles), Norman Rockwell Museum (7.2 miles), and Tanglewood (4.3 miles).
This two-bedroom, three-bathroom vacation home sleeps six guests and boasts a fully equipped kitchen, private deck with scenic pond views, access to resort amenities including indoor/outdoor pools, a fitness center, and a sauna.
Hip Stockbridge Cabin - A Stroll To The Lake - Stockbridge, MA
9.8 254 reviews

Hip Stockbridge Cabin - A Stroll To The Lake

cabin, Stockbridge
This Stockbridge cabin is located in a serene lake neighborhood with a charming bohemian interior, just steps away from the picturesque Stockbridge Bowl. It has excellent user, location, and cleanliness ratings.
The cabin has a floor area of 900 square feet and can accommodate up to 6 guests. It features a cozy sleeping loft, a reading nook, and a fieldstone fireplace. The spacious yard, sunny deck, and outdoor amenities make it perfect for relaxation and outdoor entertainment.

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

Classic Stockbridge Cottage - Stockbridge, MA
10 19 reviews

Classic Stockbridge Cottage

apartment, Stockbridge
This charming cottage is located in a quiet Stockbridge neighborhood, just a short walk from Chesterwood and the Rockwell Museum, and a quick drive to Tanglewood and the Berkshire Botanical Garden. It has received excellent user ratings and is perfect for families or groups of friends looking for a comfortable and spacious vacation home.
The cottage offers 2,770 square feet of living space with four bedrooms and three bathrooms, comfortably accommodating up to eight guests. Amenities include a fully equipped kitchen, central air conditioning, a washer and dryer, and a large outdoor terrace with plenty of space for relaxing and dining.
Renovated Downtown 1bedroom - Stockbridge, MA
10 26 reviews

Renovated Downtown 1bedroom

apartment, Lenox
This newly renovated apartment is centrally located in the heart of historic downtown Lenox, steps away from Main Street's boutiques, restaurants, and cultural attractions. With excellent user, location, and cleanliness ratings, this apartment offers a comfortable and convenient stay for up to 4 guests.
The apartment features a well-equipped kitchen, a comfortable queen bed, and a pull-out sofa bed. It also boasts a stylish interior with a sectional sofa and a dining table for two. Guests can enjoy free WiFi, keyless entry, smart TVs, and central heating and air conditioning.
Historic 1810 Farmhouse - Fully Renovated - Stockbridge, MA
9.9 154 reviews

Historic 1810 Farmhouse - Fully Renovated

apartment, West Stockbridge
This charming cottage is located in the heart of West Stockbridge, steps away from the town center and a short drive from iconic landmarks. With excellent user, location, and cleanliness ratings, this cottage is a top choice for travelers.
The cottage features 3 bedrooms, 2 bathrooms, and can accommodate up to 7 guests. It offers a cozy and inviting interior, a spacious outdoor space, and accessible features. Guests can enjoy amenities such as a fully equipped kitchen, air conditioning, a garden, and parking. The cottage also provides activities such as puzzling and plenty of space for play, making it an ideal choice for families.
Berkshires Forest Retreat With Hot Tub - Stockbridge, MA
10 85 reviews

Berkshires Forest Retreat With Hot Tub

apartment, Stockbridge
This Stockbridge apartment is located just a short drive from Tanglewood and Lenox, offering easy access to the Berkshires' cultural attractions and scenic beauty. With excellent ratings for location, cleanliness, and user experience, this rental is a top choice for families and groups.
This spacious home features 3 bedrooms and 2 bathrooms, comfortably accommodating up to 7 guests. Enjoy the expansive backyard with a fire pit, swing set, hot tub, and a large deck, perfect for relaxing and entertaining.

Best Stockbridge, MA accommodation with parking

Justice's Birthplace: King Bed, Hearths, Gardens - Stockbridge, MA
9.7 84 reviews

Justice's Birthplace: King Bed, Hearths, Gardens

house, Lee
This charming farmhouse is located in Stockbridge, just a short distance from the town center and within easy reach of numerous attractions like The Mount, the Norman Rockwell Museum, and the Lee Premium Outlets. The house has received excellent ratings for its location, cleanliness, and overall experience.
The first-floor apartment offers a private entrance, porch, and gardens, comfortably accommodating up to four guests. Enjoy modern appliances, separate utilities, and a convenient location near ski resorts and cultural landmarks.
Modern Barn In The Heart Of The Berkshires - Stockbridge, MA
9.8 168 reviews

Modern Barn In The Heart Of The Berkshires

house, Stockbridge
This unique and charming renovated 1940s dairy barn in Stockbridge offers a tranquil escape just minutes from Main Street, Tanglewood, and the Stockbridge Bowl. With excellent user, location, and cleanliness ratings, this house is a great choice for travelers visiting Stockbridge.
The house has 2 bedrooms, 1 bathroom, and can accommodate up to 4 guests. It features a fully equipped kitchen, air conditioning, a garden, parking, and a large Roku TV for entertainment. Guests can also enjoy outdoor grilling and dining, and have the option to indulge in authentic home-cooked Indian meals prepared by the host.
Light-filled Carpenter's Cottage - Stockbridge, MA
10 5 reviews

Light-filled Carpenter's Cottage

apartment, Stockbridge
This Stockbridge cottage is situated on a south-facing hill with views of Monument Mountain, offering a private retreat just a short distance from family, with the highway's hum audible.
This pet-friendly apartment accommodates two guests and features a kitchen, air conditioning, one bathroom, a private deck with seating for six, and access to explore the surrounding woods and stream.
Cozy Lenox Retreat ~ Explore~rejuvenate - Stockbridge, MA
9.9 83 reviews

Cozy Lenox Retreat ~ Explore~rejuvenate

apartment, Lenox
This Lenox, Massachusetts cottage, two miles from Lenox's town center, boasts a secluded setting in the Berkshires with a rich history as a creative retreat for renowned artists, including the Coen Brothers.
This newly renovated (2022) two-bedroom, one-bathroom house sleeps three to four adults comfortably, offering a spacious open-concept layout with a fully equipped kitchen, private deck, and yard, plus air conditioning, internet, and parking.

Best Stockbridge, MA lodging with a pool

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

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

Historic Stockbridge Villa On 25 Acres

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

Spacious 4br Central-berkshires Home With Pool!

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

Berkshires Mid-century Retreat!

apartment, West Stockbridge
Tranquil Lakeside Escape In The Berkshires - Stockbridge, MA
9.0 2 reviews

Tranquil Lakeside Escape In The Berkshires

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.

The Blue House On The Bend - Stockbridge, MA
10 79 reviews

The Blue House On The Bend

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.

The Great Escape Berkshire Ski Cottage W/hot Tub! - Stockbridge, MA
9.9 112 reviews

The Great Escape Berkshire Ski Cottage W/hot Tub!

apartment, Great Barrington
Hike, Fish & Ski: Riverside Barn Loft In Lee - Stockbridge, MA
No reviews

Hike, Fish & Ski: Riverside Barn Loft In Lee

apartment, Lee
Stockbridge In-town Escape - Stockbridge, MA
No reviews

Stockbridge In-town Escape

apartment, Stockbridge
Meadow`s Edge: A Modern Retreat - Stockbridge, MA
No reviews

Meadow`s Edge: A Modern Retreat

apartment, Stockbridge
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