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.

Quaint & Cozy Loft - Stockbridge, MA
10 3 reviews

Quaint & Cozy Loft

apartment, Stockbridge
This Stockbridge loft apartment offers stunning views of Norman Rockwell's home and the village street, providing easy access to local attractions.
The one-bedroom, one-bathroom unit features a galley kitchen, fireplace, hardwood floors, and accommodates two guests, perfect for exploring Stockbridge's historical sites and charming village.
Stockbridge Escape - Stockbridge, MA
10 3 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
9.0 4 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.

Exceptional Stockbridge Retreat - Stockbridge, MA
10 21 reviews

Exceptional Stockbridge Retreat

apartment, Stockbridge
This Stockbridge apartment rental is conveniently located near the Norman Rockwell Museum and Taglewood, offering easy access to Stockbridge Bowl and the town's attractions.
The three-bedroom, one-bathroom unit sleeps eight guests and includes a fully equipped kitchen with dishwasher, air conditioning, a garden, parking, and internet access; enjoy nearby swimming, boating, and cultural experiences.
Cozy, Welcoming Berkshires Cabin  Come Unplug! - Stockbridge, MA
9.7 21 reviews

Cozy, Welcoming Berkshires Cabin Come Unplug!

apartment, Stockbridge
This Stockbridge vacation home in Mahkeenac Heights is located 2 miles from Tanglewood and a short walk from Stockbridge Town Beach, offering easy access to Lenox.
The two-bedroom, one-bathroom house features a queen and full bed, plus a sleeping loft with two twins, accommodating up to five guests; amenities include a kitchen with dishwasher, Wi-Fi, a three-season porch, deck, fire pit, and pet-friendly options (dogs only, restrictions and fees apply).
Luxury Fox Hollow Estate Home On Laurel Lake - Dream Location, Hot Tub, Kayaks++ - Stockbridge, MA
9.4 65 reviews

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

apartment, Lee
This waterfront Cape Cod-style house is situated in the heart of Lenox, within walking distance of the Edith Wharton Estate and a short drive from Lee's cultural attractions and outdoor activities. The house has an excellent user rating.
The house has a floor area of 2700 square feet and can accommodate up to 14 guests. It has 5 bedrooms, 3 bathrooms, a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a swimming pool, a jacuzzi, a garden, and parking. The house also offers amenities such as a pool table, HD Smart TVs, wood-burning fireplaces, a wine cooler, a hot tub, an outdoor barbecue, a tennis court, kayaks, canoes, and a rowboat.
Berkshires Forest Retreat With Hot Tub - Stockbridge, MA
10 83 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.

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

Greenhouse - Stockbridge, MA
10 131 reviews

Greenhouse

apartment, Lee
The GreenHouse guest cottage, located in Lee, Massachusetts, is a short walk from Lee's town center and near the cultural attractions of Stockbridge and Lenox, situated on the grounds of the historic Hyde House, a National Register of Historic Places property.
This two-bedroom, one-bathroom guest house sleeps four and features a kitchen with a fridge, freezer, and microwave, air conditioning, parking, and access to potentially shared amenities of the main Hyde House; enjoy a peaceful Berkshires getaway in this unique historic setting.
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 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.
Cozy. Clean. Free Bagel Shop. 3 Fireplaces. - Stockbridge, MA
10 2 reviews

Cozy. Clean. Free Bagel Shop. 3 Fireplaces.

apartment, Great Barrington
This three-bedroom house is located a short distance from downtown Great Barrington, providing easy access to the Mahaiwe Performing Arts Center and the W.E.B. Du Bois Boyhood Homesite, and is a short drive to Butternut ski slopes.
This rental sleeps six guests and features a full kitchen with a microwave oven and dishwasher, air conditioning, spa amenities, parking, three wood-burning fireplaces, a king-sized bed in the primary suite, and a wood-fired pizza oven, with complimentary breakfast bagels and hot beverages from the Great Barrington Bagel Company, located 5,280 feet away.
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.

Best Stockbridge, MA accommodation with parking

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, offers excellent proximity to downtown Lee, the weekly farmers market, Starving Artist Cafe, Big Y supermarket, and is a short drive from Stockbridge (5 minutes), Lenox (10 minutes), and Great Barrington (15 minutes).
The 10-guest house features a fully equipped kitchen with a butcher block island, multiple common areas including a game room, outdoor amenities such as a BBQ and firepit, and is near the Housatonic River and Greenock Country Club.
Stylish Berkshires Retreat - Stockbridge, MA
9.0 2 reviews

Stylish Berkshires Retreat

apartment, Lee
This 2-bedroom apartment in Lee offers proximity to Pleasant Valley Wilderness Sanctuary, Monument Mountain Reservation, Tanglewood Music Center, and the Animagic Museum of Animation.
This dwelling accommodates up to 4 guests with two queen beds and features air conditioning, heating, and a hair dryer in its single bathroom, serving as an ideal base for exploring the Berkshire region.
The Lenox Nook - Stockbridge, MA
9.8 12 reviews

The Lenox Nook

apartment, Lenox
This Lenox apartment is centrally located, within walking distance of downtown Lenox's restaurants and shops, and a short drive from Tanglewood and Guido's Market.
This two-bedroom, one-bathroom rental offers a full kitchen with a fridge, freezer, microwave, and dishwasher, accommodating up to four guests and features a garden and parking.
The Lenox Cottage - Stockbridge, MA
10 17 reviews

The Lenox Cottage

apartment, Lenox
This Lenox, Massachusetts cottage is a seven-minute walk downhill from Lenox town center and a short uphill walk from Kennedy Park.
The one-bedroom, one-bathroom house sleeps three guests and features a full kitchen, Wi-Fi, a stereo/record player, and a piano; pets (dogs only) are allowed for a fee.

Best Stockbridge, MA lodging with a pool

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

Condo ∙ 2 Bedrooms ∙ 6 Guests - Stockbridge, MA
No reviews

Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Lenox
The Summerwood Hideout | Mins To Downtown!  Pool - Stockbridge, MA
9.0 4 reviews

The Summerwood Hideout | Mins To Downtown! Pool

apartment, Great Barrington
General Williams Estate House Lenox/stockbridge - Stockbridge, MA
9.8 117 reviews

General Williams Estate House Lenox/stockbridge

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

Stunning Luxury Home With Pool

apartment, Great Barrington

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.

Lenox, Ma Getaway, Mile To Town! - Stockbridge, MA
9.7 370 reviews

Lenox, Ma Getaway, Mile To Town!

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.

Sweet Cozy Victorian In Housatonic. Close To Everything. - Stockbridge, MA
9.8 7 reviews

Sweet Cozy Victorian In Housatonic. Close To Everything.

apartment, Great Barrington
Sophisticated Lenox Retreat By Evergreen Home - Stockbridge, MA
9.9 67 reviews

Sophisticated Lenox Retreat By Evergreen Home

apartment, Lenox
Raised Ranch Serenity - Stockbridge, MA
9.5 19 reviews

Raised Ranch Serenity

apartment, Lenox
Seeking "School Year" Sept-june. Please Inquire! - Stockbridge, MA
No reviews

Seeking "School Year" Sept-june. Please Inquire!

apartment, Stockbridge
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