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Holiday houses in Stockbridge

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Quick stats about holiday rentals in Stockbridge

  • Total holiday rentals

    Explore 160 holiday rentals in Stockbridge

  • Nightly prices starting at

    Stockbridge holiday rentals start at $193 NZD per night before taxes and fees

  • Verified guest reviews

    Over 5,310 verified reviews to help you choose

  • Family-friendly holiday rentals

    90 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 50 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    160 of Stockbridge holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Stockbridge rentals

  • 4.8 Average rating

    Stockbridge stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Stockbridge's top spots, include Norman Rockwell Museum, Naumkeag, and Berkshire Botanical Garden

Top-rated holiday rentals in Stockbridge

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Cabin in East Nassau

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

LocationFamilyKitchen

4.97 out of 5 average rating, 109 reviews
Guest favourite
An open living area showcases rustic wooden beams and a cozy gas fireplace. A modern gray sofa faces the fireplace, complemented by a glass coffee table with a vase of pink flowers. Natural light floods in from the glass doors, leading to the lush green outdoor space.
Home in Stockbridge

Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

FamilyValueAmenities

4.95 out of 5 average rating, 191 reviews
Top Guest favourite
A charming outdoor seating area is situated under a spacious pergola, designed with warm lights. Comfortable seating is set on a stone patio, with a grill nearby, surrounded by a grassy yard. Soft clouds and a gentle twilight sky provide a serene backdrop.
Home in Lee

Berkshire 4 season home

The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.

FamilyLocationLayout

4.98 out of 5 average rating, 253 reviews
Guest favourite
A modern kitchen features clean lines and natural light. The space includes a refrigerator, stove, and a dining table with two chairs. Soft white cabinetry is complemented by a wooden tabletop, while a window offers views of the outdoors, enhancing the open and airy feel.
Apartment in Stockbridge

Stockbridge private apartment

Newly renovated apartment, just one mile from Downtown Stockbridge. This cozy apartment offers gorgeous mountain views and access to the lush backyard area. 10 minutes from local attractions such as Tanglewood, the Stockbridge bowl, and Kripalu. Close to many hiking trails, including backyard access to a riverside walking trail This apartment is attached to the owners house, however it has a private entrance and is completely separate. The parking area is shared- there is space for two cars.

LocationFamilySolo travel

4.92 out of 5 average rating, 103 reviews
Guest favourite
An open living space features a large sectional sofa surrounding a central glass coffee table. A decorative chandelier hangs from the exposed wooden beams. Natural light streams in through multiple floor-to-ceiling windows, revealing views of the surrounding greenery.
Barn in East Chatham

Luxury Barn Near Hudson with New Private Sauna

A secluded luxury barn retreat near Hudson and the Berkshires, now featuring a private sauna for year-round relaxation. Set on eight private acres where New York meets the Berkshires, this architect-designed 19th-century barn combines soaring ceilings, original beams and contemporary comforts. Enjoy a chef’s kitchen, two fireplaces, designer interiors, peaceful outdoor spaces and access to nearby Queechy Lake. Minutes from Chatham and an easy drive to Hudson, Great Barrington and Tanglewood.

ValueLocationKitchen

4.96 out of 5 average rating, 114 reviews
Top Guest favourite
A winter scene depicts a charming town square with snow-covered ground, featuring a building adorned with a glowing Christmas tree in its window. Vintage cars are parked in front, while small groups of people are visible, creating a festive atmosphere against a twilight sky.
Apartment in Stockbridge

Historic,Famous,Iconic, Unforgettable Berks Escape

PICTURE IT...You can put yourself in the "famed" Norman Rockwell Main Street at Christmas Painting! That's Right,Cozy, Intimate,Magical and all to yourself.Fully equipped with all the comforts of home. Small Town Charm,Big time Historic setting in the heart of Downtown Stockbridge! Spend your afternoon sipping Tea or Wine looking out the iconic picture window Norman Rockwell installed himself. The one where the Christmas Tree Glows in a room that was Norman Rockwell's Studio from 1953-1957

FamilyValueTV

4.96 out of 5 average rating, 125 reviews
Guest favourite
Cabin in Stockbridge

Hip Stockbridge Cabin - A stroll to the lake

Welcome to our stylish cabin! Relax in the spacious yard & sunny deck. Cozy fieldstone fireplace, vaulted ceilings & skylights. The cottage features gorgeous pine wood walls & fantastic interior design. Unwind in the reading nook, relax in the en suite bedroom with skylight, or put on your favorite vinyl. Kids will adore the sleeping loft. Just a 9 minute walk or 2 minute drive to the public beach (the beautiful Stockbridge Bowl). BBQ grill, outdoor fire pit . Tanglewood minutes away.

LocationFamilySleep quality

4.89 out of 5 average rating, 255 reviews
Guest favourite
A modern, renovated barn is set against a backdrop of lush greenery. Two brightly colored lounge chairs and a reclining chair are positioned on the grassy area, inviting relaxation. Large windows reflect the surrounding trees, emphasizing the tranquil outdoor setting.
Guesthouse in Stockbridge

Modern barn in the heart of the Berkshires

Modern, renovated dairy barn in the heart of the Berkshires. Located on 3.5 acres with beautiful views and close to everything. 1.5 miles to Main St Stockbridge/Red Lion Inn, 5 minutes to Tanglewood, 5 minutes to the Stockbridge Bowl and beautiful hiking trails, under 10 minutes to Lenox . This is the perfect base for exploring the Berkshires or a great getaway for relaxing and enjoying nature. Family and pet friendly! *Please read Interaction with Guests section before booking*

ValueFamilyParking

4.91 out of 5 average rating, 175 reviews
Guest favourite
An entryway features a grey console table with glass-front cabinets, topped by a table lamp and a potted plant. A round mirror hangs above the table, while a doorway leads into the home, revealing glimpses of the kitchen and hallway beyond.
Home in Stockbridge

Sun-filled, Charming Stockbridge Classic- In Town!

Beautiful remodel on a classic old, well-appointed New England house located in the middle of town on a dead-end road leading to hiking trails for Laura's Tower. A quick walk to Downtown Stockbridge, Red Lion Inn, gas station, cafes, markets, shops... everything you need. A park sits directly across the street with open acreage, swings, sandbox, skate park. Parking available on site. Located within minutes of four season activities- happy to make recommendations!

ValueFamilyAir conditioning

4.94 out of 5 average rating, 168 reviews
Top Guest favourite
Guesthouse in Stockbridge

Bitty Berkshire Bungalow

Just 2 miles from historic Stockbridge's Red Lion Inn, 1 mile from the Norman Rockwell Museum and the Berkshire Botanical Garden, 15 minutes from Bosquet ski resort, 12 minutes from Tanglewood, and around the corner from Chesterwood, in the lush forest of Massachusetts' Berkshire mountains, this cozy "bitty bungalow" is the perfect place from which to foray out on wonderful adventures in this vacation wonderland, returning for quiet rest and renewal.

FamilyValueAmenities

4.98 out of 5 average rating, 61 reviews
Top Guest favourite
A modern kitchenette is visible, featuring black cabinetry and open shelving with dishware. A dining area with a table and four chairs is situated nearby, while light streams in through a skylight and window, illuminating the open space.
Guesthouse in Stockbridge

Modern studio with views of the treetops

Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

LocationValueNearby

4.96 out of 5 average rating, 316 reviews
Top Guest favourite
A charming cottage is framed by vibrant flowering shrubs and greenery. The front porch is adorned with decorative elements, while large windows invite natural light into the space. A wooden fence encloses the front garden, enhancing the quaint and inviting atmosphere.
Cottage in Great Barrington

Artist Cottage

Artsy vintage cottage with a private lodge in a quiet Berkshire neighborhood. Backyard opens to woods with trails nearby. Enjoy fireplaces and hot tub in winter, waterfall and outdoor shower in summer. Upstairs queen ensuite with bathroom and soaking tub; downstairs retro kitchen, living room, and full bath with shower. Lodge offers comfy seating, farm table, and big-screen TV. High-speed internet, Prime & Spectrum TV.

LocationFamilyAir conditioning

4.94 out of 5 average rating, 355 reviews

Popular amenities for Stockbridge holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Stay near Stockbridge's top sights

Norman Rockwell Museum

483 locals recommend

Mount Edith Wharton's Home

259 locals recommend

Kripalu Center for Yoga & Health

169 locals recommend

Naumkeag

187 locals recommend

Berkshire Botanical Garden

185 locals recommend

Shakespeare & Company

168 locals recommend

Other great holiday rentals in Stockbridge

Top Guest favourite
A bright living area features large windows that allow natural light to flood in, showcasing views of nearby trees in autumnal colors. Two modern armchairs and a navy sofa are arranged on a patterned area rug, with a coffee table positioned centrally.
Home in Stockbridge

Stockbridge pied-à-terre

LocationQuietIndoor spaces

4.96 out of 5 average rating, 47 reviews
Top Guest favourite
Home in Pittsfield

Cozy cottage on peaceful pond

LocationFamilyComfort

5.0 out of 5 average rating, 38 reviews
Superhost
Home in Stockbridge

Meadow's Edge - Modern Retreat w/ In Law Suite

FamilyLocationBackyard

5.0 out of 5 average rating, 4 reviews
Top Guest favourite
A hammock is gently draped between trees, overlooking a tranquil pond. Nearby, a dock extends into the water, surrounded by lush greenery and lily pads, providing a serene spot for relaxation and contemplation.
Cabin in Stockbridge

Lakeshore cabin with beach and dock

FamilyLocationCondition

4.98 out of 5 average rating, 64 reviews
Top Guest favourite
An open living area features cathedral ceilings supported by wooden beams. A mix of bright furniture includes a yellow sofa and a red sectional. Large windows allow ample natural light, illuminating the wooden floors. A cozy wood stove complements the inviting space.
Home in Stockbridge

Secluded Family Home in Serene Stockbridge Woods

FamilyLocationBackyard

4.99 out of 5 average rating, 88 reviews
Superhost
Home in West Stockbridge

Exceptional Stockbridge Retreat

FamilyValueLaundry

4.92 out of 5 average rating, 25 reviews
Guest favourite
Home in Stockbridge

Classic Stockbridge Cottage

LocationFamilyGetting around

4.92 out of 5 average rating, 37 reviews
Top Guest favourite
The exterior of a transformed church features a pointed steeple and a central double door framed by a decorative arch. Stained-glass windows are visible, adding a historic charm against the dark wood siding. The surrounding area is lined with trees, hinting at the serene natural setting.
Home in Great Barrington

Berkshires Black Abbey

ValueLocationTV

5.0 out of 5 average rating, 47 reviews

When is the best time to visit Stockbridge?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$522 NZD$615 NZD$578 NZD$559 NZD$569 NZD$604 NZD$744 NZD$692 NZD$613 NZD$569 NZD$569 NZD$595 NZD
Avg. temp-4°C-3°C2°C9°C15°C20°C23°C22°C18°C11°C5°C-1°C

Frequently Asked Questions

  • What are the best places to stay in Stockbridge?

    Vacation rentals in central Stockbridge, cottages around scenic areas, and homes near parks are favored for their access to local attractions and comfort. Many options blend historic charm with modern amenities.

  • What are the best things to do in Stockbridge with kids?

    Families can explore interactive museums, wander through botanical gardens, and enjoy nature trails suited for young hikers. Seasonal activities, such as outdoor performances or local fairs, are frequently suggested for children.

  • What are some of the best things to do in Stockbridge?

    Wander through historic downtown streets, visit art museums, and stroll botanical gardens. Stockbridge also has opportunities for outdoor recreation and hosts community arts events throughout the year.

  • How is the weather in Stockbridge?

    Stockbridge has cold winters near 16–38°F (-9–3°C), and warm summers reaching 62–84°F (17–29°C), with spring and fall offering mild temperatures and moderate rainfall. Layered clothing and a waterproof jacket suit the changing conditions.

  • When is the best time to visit Stockbridge?

    Late spring through early fall is frequently suggested for milder temperatures, blooming gardens, and outdoor events. Winter draws visitors with festive decorations and seasonal activities, though colder weather is typical.

  • What are the best places to visit in Stockbridge?

    Stockbridge has a renowned art museum, historic estates, and tranquil gardens frequently suggested by visitors. The downtown area, with shops and local eateries, is also popular for exploring.

  • What are some hiking trails in Stockbridge?

    Explore forested routes and gentle pathways through preserves, as well as garden walks that highlight local plant life. Trails in and around Stockbridge vary in difficulty and scenery, appealing to a range of hikers.

  • What are some family activities we can do in Stockbridge?

    Try hands-on museum exhibits, explore nature trails suited for all ages, or join seasonal arts workshops. Stockbridge has family-oriented events and outdoor recreation throughout the year.

  • What are some of the best day trip ideas from Stockbridge?

    Plan to discover nearby villages with charming shops, historic landmarks, or art centers. Outdoor destinations around Stockbridge, including lakes and hiking spots, are often recommended for a change of scene.

  • Are there any pet friendly accommodations available in Stockbridge?

    Many accommodations in Stockbridge welcome pets, particularly cottage rentals and some homes near outdoor areas. Look for rental listings that mention pet-friendly amenities.

  • What are some local tips for visiting Stockbridge?

    Locals suggest checking for seasonal art shows and arriving early at the most popular attractions to enjoy quieter moments. Dining reservations are often recommended, especially during busy seasons or festivals.

  • What is Stockbridge known for?

    Stockbridge is known for its quaint downtown, historic architecture, and connections to American art and literature. The town frequently draws visitors seeking both cultural experiences and scenic landscapes.

  • What are the best hidden gems to explore in Stockbridge?

    Discover lesser-known art installations, quiet garden spaces, or small community markets around town. Stockbridge also has historic sites tucked away from the main streets, inviting thoughtful exploration.

  • What are the best foods to try in Stockbridge?

    Stockbridge has locally rooted cuisine highlighting New England classics, including farm-fresh produce, artisanal cheeses, and baked goods. Seasonal menus often emphasize comfort dishes and regional specialties.

  • What should I bring for a trip to Stockbridge?

    Pack comfortable shoes for walking, layers to manage seasonal changes, and a rain jacket—especially for spring or summer visits. In colder months, warm clothing and boots help with outdoor explorations.

  • What is the nightlife in Stockbridge like?

    Stockbridge has a relaxed evening atmosphere, featuring cozy taverns, casual restaurants, and occasional live music at local venues. Many spots focus on community gatherings, arts events, and low-key entertainment.

  • What are the most popular events or festivals in Stockbridge?

    Stockbridge has art festivals, holiday celebrations, and summer concerts that are often recommended. Events anchored around late spring and the winter holidays draw many visitors for community gatherings.

  • Are there family friendly vacation rentals in Stockbridge?

    Stockbridge has many vacation rentals that accommodate families, including spacious homes and cottages near parks or local attractions. Options often feature amenities like full kitchens and outdoor areas.

Destinations to explore