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Holiday houses in Great Barrington

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Quick stats about holiday rentals in Great Barrington

  • Total holiday rentals

    Explore 230 holiday rentals in Great Barrington

  • Nightly prices starting at

    Great Barrington holiday rentals start at $50 NZD per night before taxes and fees

  • Verified guest reviews

    Over 12,690 verified reviews to help you choose

  • Family-friendly holiday rentals

    170 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 120 rentals that welcome pets

  • Holiday rentals with a pool

    20 properties feature pools

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

  • Wi-Fi availability

    230 of Great Barrington holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Great Barrington rentals

  • 4.9 Average rating

    Great Barrington stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated holiday rentals in Great Barrington

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

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Top Guest favourite
A cozy living room features a light sofa and two armchairs flanking a wooden coffee table. A decorative rug with intricate patterns lies beneath. Natural light filters through multiple bay windows, highlighting the serene and vintage-inspired decor.
Apartment in Great Barrington
5.0 out of 5 average rating, 147 reviews

Walk Everywhere! | Relax in Easy Elegance!

Gracious in-town apartment feels like home: living and dining rooms, kitchen, 2 bedrooms, 2 baths—all just for you and your group. Walk to shops, restaurants, theaters, farmers’ market. Drive to more nearby arts offerings, hiking, skiing, swimming. Spectrum WiFi; please note, there is no TV. Bedrooms are small but with plenty of space to spread out, relax, read, play games or enjoy a meal in the entire apartment. The shared porch is available for morning coffee, evening cocktails or a good book.

LocationFamilyWi-Fi

Top Guest favourite
A modern bedroom features a spacious bed with high-end linens, flanked by two stylish chairs. A desk and chair sit by the window, and an arched door adds architectural interest. Natural light illuminates the room, highlighting a unique wall design in neutral tones.
Apartment in Great Barrington
4.92 out of 5 average rating, 179 reviews

King Bed | Patio | 2m to Ski Resort

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. *1.5 miles to Downtown *1.3 miles to Mahaiwe Performing Arts Center *44 miles to Albany International Airport *4.5 miles to Great Barrington Airport *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *58"Tv with Hulu Live

FamilyLocationKitchen

Guest favourite
A dining area features a wooden table surrounded by four black chairs. A vase with greenery is centered on the table. In the background, a cozy seating area with a sofa is visible, illuminated by natural light from a nearby window.
Guesthouse in Great Barrington
4.95 out of 5 average rating, 173 reviews

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

ValueLocationNearby

Top Guest favourite
Home in Lee
4.99 out of 5 average rating, 316 reviews

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

LocationFamilyKitchen

Top Guest favourite
A bright living room is highlighted by a grand piano and a modern gas fireplace, both set against a light brick wall. Large windows provide natural light, and wooden flooring adds warmth. A comfortable dark sofa and armchairs are arranged around a glass coffee table.
Home in Great Barrington
4.99 out of 5 average rating, 94 reviews

Stunning luxury home with pool

Welcome to our weekend home in the Berkshires! We now rent it out when we’re not there, following a top-to-bottom renovation with all new furniture, and hope our guests enjoy it as much as we do. Our home is in Great Barrington, 2.5 hours' drive from NYC, surrounded by trees and parkland (Monument Mountain is next door). Yet it's less than 10-15 minutes' drive to town, shopping, restaurants, skiing, and Tanglewood. Come enjoy the Berkshires with complimentary gourmet coffee!

FamilyValueHospitality

Top Guest favourite
A modern farmhouse bungalow is nestled among lush greenery along a brook. The red exterior is complemented by white trim and a front porch. A wooden bench sits by the water's edge, inviting relaxation amidst the tranquil natural surroundings.
Bungalow in Egremont
4.99 out of 5 average rating, 138 reviews

3-bedroom Berkshire bungalow on 2.5 peaceful acres

Modern farmhouse bungalow with private bridge and brook! Offering privacy as well as nearby nightlife, set upon 2.5 acres of beautiful Berkshire landscape but only 7 minutes to downtown Great Barrington and a short drive to Catamount and Butternut ski area. Mountains, waterfalls, countless hikes and bike routes, farmers' markets, coffee shops, breweries, Shakespeare and Co, Tanglewood, and world-class restaurants all come together in this quintessential New England community.

FamilyLocationSleep quality

Top Guest favourite
A serene bedroom is presented with a spacious bed adorned with soft linens and a cozy throw. Two bedside tables hold elegant lamps, and natural light floods the room through large windows. A decorative wreath hangs above the headboard, enhancing the tranquil ambiance.
Home in Sheffield
4.99 out of 5 average rating, 133 reviews

Belle Meade

Open concept home with a Zen feel and made for relaxation. Nestle into the covered porch and spend hours of peaceful contemplation with nature all around! When you’ve had enough recharging, plan a backroad trip to endless possibilities. Tanglewood and Jacob’s Pillow are nearby via beautiful country roads. There are hikes for any level. Great restaurants, farmer’s markets and Guidos gourmet market just minutes away. Eat out or stay in with a cook’s kitchen and grill deck.

LocationValueView

Top Guest favourite
The spacious living room features large windows that provide scenic views of the mountains and lake. A comfortable sectional sofa is complemented by a decorative throw and cushions. The ceiling is elevated with wooden beams, and stylish decor enhances the inviting atmosphere.
Home in Monterey
4.96 out of 5 average rating, 307 reviews

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

ValueLocationParks

Superhost
A bright living area is featured, showcasing large windows that provide views of the surrounding nature. A fireplace is positioned centrally, complemented by a light-toned wooden sofa and a cozy chair. A dining table for two is visible, along with a small shelf and potted plants.
Cottage in Great Barrington
4.94 out of 5 average rating, 222 reviews

The Cottage at The Barrington House

Welcome to the Cottage at the Barrington House! The Barrington House is nestled in the serene Berkshires Mountains - which have long been a sanctuary for weary city dwellers seeking breathing space, a perfect retreat for artists, writers and thinkers! It's sprawling grounds offer stunning views of lush valleys and distant peaks, while the interior features a fireplace, cozy reading nook, and unlimited windows that invite the natural world inside.

LocationFamilyBackyard

Top Guest favourite
The charming farmhouse features a covered porch with seating, surrounded by a vibrant garden filled with colorful flowers. Solar panels are visible on the roof, while a grassy area and a small fire pit enhance the outdoor space, inviting relaxation in a natural setting.
Home in Great Barrington
5.0 out of 5 average rating, 115 reviews

Walk to Town! Great Barrington 4-bedroom farmhouse

Enjoy the yard and garden at this charming 4-bedroom in-town farmhouse. The garden features various fruits and vegetables in season. Stroll to Great Barrington's restaurants and shops. Hike the woodland trail up the hill for a swim at nearby Lake Mansfield. Retreat to the private garden hideaway. This place has something for everyone who wants to relax in a cozy setting yet still be near everything Great Barrington has to offer.

LocationFamilyLayout

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
4.93 out of 5 average rating, 352 reviews

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.

ValueLocationCheck-in

Top Guest favourite
The kitchen features light-colored cabinetry with black hardware, complemented by a wood countertop. A refrigerator and an oven with a stovetop are included. A dining table with light wooden chairs is positioned nearby, and a rug adds texture to the hardwood flooring.
Home in Great Barrington
4.97 out of 5 average rating, 138 reviews

Prime location for the best of the Berkshires

Our warm and welcoming little house has been designed and outfitted to be highly accommodating and comfortable. Our country living location is private but also super convenient: just a mile from Butternut Basin Ski Resort; walking distance to the Appalachian Trail; an easy 5 minute drive to Main Street Great Barrington; and shopping for staples is likewise close by.

ValueFamilyWi-Fi

Popular amenities for Great Barrington holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Great Barrington's top sights

Butternut Ski Area and Tubing Center

315 locals recommend

Monument Mountain Reservation

148 locals recommend

Monument Mountain

81 locals recommend

Lake Buel

7 locals recommend

Mansfield Pond

49 locals recommend

Beartown State Forest

37 locals recommend

Other great holiday rentals in Great Barrington

Top Guest favourite
A charming red house is framed by green trees and colorful plants in front. The home features a welcoming porch adorned with vibrant flowers, creating a harmonious blend with the surrounding natural landscape.
Apartment in Great Barrington
4.98 out of 5 average rating, 48 reviews

The River’s Whisper

LocationFamilyKitchen

Top Guest favourite
An outdoor area features a wooden barrel sauna alongside a modern hot tub. The hot tub's white surface contrasts with the natural wood of the sauna, set against a backdrop of lush green trees and a wooden fence, creating a serene environment for relaxation.
Home in Great Barrington
5.0 out of 5 average rating, 56 reviews

Sauna + Hot Tub Escape | Private & Pet Friendly

LocationFamilyHeating

Top Guest favourite
A charming house is nestled among autumn foliage, displaying warm earthy tones. A winding stone pathway leads to the entrance, framed by a well-maintained stone wall and lush greenery. Colorful leaves adorn the surrounding trees, creating a serene and inviting landscape.
Home in Great Barrington
4.98 out of 5 average rating, 45 reviews

Seekonk Hill

ValueLocationSleep quality

Top Guest favourite
A modern living area features comfortable seating arrangements with plush chairs and a sofa. The open kitchen, equipped with stainless steel appliances and a central island, is partially visible. Natural light is welcomed through large windows, enhancing the warm, inviting decor.
Loft in Great Barrington
5.0 out of 5 average rating, 64 reviews

The Nest 5 min walk to downtown Great Barrington

FamilyLocationGetting around

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
5.0 out of 5 average rating, 45 reviews

Berkshires Black Abbey

LocationFamilyIndoor spaces

Guest favourite
The living room features a bright and airy design with large windows that provide natural light. A soft sectional sofa offers ample seating, facing a cozy fireplace surrounded by stone. Decorative art pieces and a wooden ceiling enhance the room's warmth and character.
Home in Great Barrington
4.97 out of 5 average rating, 61 reviews

Hilltop Ski and Sun Chalet with Hot Tub

ValueLocationTV

Top Guest favourite
An aerial view captures the tranquil lakeside retreat surrounded by lush greenery. The house is positioned near the water, offering easy access to the scenic lake, which is nestled within a rich landscape of trees and foliage.
Home in Great Barrington
4.97 out of 5 average rating, 78 reviews

Waterfront Modern Lake Mansfield Retreat

FamilyLocationOutdoor spaces

Top Guest favourite
A spacious great room showcases high wooden ceilings and exposed beams. Vintage furniture, including a green upholstered chair and a light brown armchair, surrounds a wooden coffee table. A rustic dining area is visible in the background, leading to the kitchen area with modern appliances.
Barn in New Marlborough
4.98 out of 5 average rating, 47 reviews

Hartsville Barn in the Berkshires

FamilyValueBathroom

When is the best time to visit Great Barrington?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$495 NZD$457 NZD$438 NZD$433 NZD$462 NZD$499 NZD$512 NZD$490 NZD$440 NZD$442 NZD$475 NZD$504 NZD
Avg. temp-4°C-2°C2°C9°C14°C19°C22°C21°C17°C10°C5°C-1°C

Frequently Asked Questions

  • What are the best places to stay in Great Barrington?

    Many visitors choose to stay near Main Street for easy access to local shops, eateries, and arts venues. Stays around the Housatonic River also draw those looking for a quieter or more scenic atmosphere.

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

    Kids can explore local parks, enjoy nature trails, or participate in seasonal outdoor theater performances. Hands-on activities at nearby museums or community events are often recommended for families.

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

    Explore Main Street for local shops and galleries, wander the Housatonic River Walk, or attend a performance at the Mahaiwe Performing Arts Center. Outdoor enthusiasts frequently suggest hiking and exploring nearby preserves.

  • How is the weather in Great Barrington?

    Great Barrington has cold winters around 16–35°F (-9–1°C), with snow common, and summers are comfortably warm at 59–82°F (15–28°C). Spring and autumn bring mild temperatures and changing scenery.

  • When is the best time to visit Great Barrington?

    Late spring through early fall is often recommended for mild weather, outdoor activities, and seasonal events. Autumn brings colorful foliage, while summer has lively markets and festivals.

  • What are the best places to visit in Great Barrington?

    Popular stops include Main Street’s shops and eateries, Monument Mountain, and the Mahaiwe Performing Arts Center. The Housatonic River Walk is also frequently suggested for a relaxing outing.

  • What are some hiking trails in Great Barrington?

    Hikers often head to Monument Mountain, Ice Glen, or the Housatonic River Walk for forested paths and scenic overlooks. These trails range from gentle walks to steeper climbs amid classic Berkshire landscapes.

  • What are some family activities we can do in Great Barrington?

    Families can explore nature preserves, play in local parks, or enjoy hands-on experiences at nearby museums. Seasonal events, markets, and outdoor theater performances are also frequently suggested.

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

    Explore the Berkshire countryside, which has scenic hiking areas, historic villages, and art museums. Nearby, you might find botanical gardens, farm stands, or locally owned galleries that showcase the region’s creative energy.

  • Are there any pet friendly accommodations available in Great Barrington?

    Pet-friendly stays are commonly found near Main Street, in the village center, and around surrounding rural areas. Many rentals have easy access to trails or green spaces for walking with your dog.

  • What are some local tips for visiting Great Barrington?

    Locals suggest starting your day early to enjoy the farmers’ market or a riverside walk, and checking community boards for pop-up events or live music. Trying local cheeses and browsing independent bookstores are favorite pastimes.

  • What is Great Barrington known for?

    Great Barrington is known for its thriving arts scene, historic Main Street, and access to Berkshire natural areas. The community values local food, creative culture, and scenic outdoor activities year-round.

  • What are the best hidden gems to explore in Great Barrington?

    You might discover independent bookstores, locally owned coffee shops, and artisan markets tucked along Main Street. Some visitors enjoy wandering quieter forest trails or visiting lesser-known historical sites around town.

  • What are the best foods to try in Great Barrington?

    Farm-to-table fare is popular, with many menus highlighting local produce, artisan cheeses, and Berkshire-grown meats. Bakeries and cafés often serve freshly baked breads, maple treats, and seasonal pies.

  • What should I bring for a trip to Great Barrington?

    Layered clothing is helpful, as temperatures can shift from cool mornings to warmer afternoons. Comfortable shoes, a rain jacket, and a reusable water bottle support outdoor exploring in changing New England weather.

  • What is the nightlife in Great Barrington like?

    Nightlife in Great Barrington has live music in casual venues, performances at the Mahaiwe Performing Arts Center, and relaxed bars featuring local brews. Evening events sometimes include readings or open mic nights around downtown.

  • What are the most popular events or festivals in Great Barrington?

    Summer frequently features outdoor concerts and local theater performances, while the fall harvest season has farmers’ markets and craft fairs. Film festivals and holiday celebrations are also often recommended around town.

  • Are there family friendly vacation rentals in Great Barrington?

    Family-friendly vacation rentals are available throughout Great Barrington, especially near parks, Main Street, and residential neighborhoods. Homes with multiple bedrooms or yards are often suggested for guests traveling with children.

Destinations to explore