
Holiday rentals in Great Barrington
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Top-rated holiday rentals in Great Barrington
Guests agree: these stays are highly rated for location, cleanliness and more.

The Old Red Barn
Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

Mid-Century Glass Octagon in the Berkshires
This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Walk Everywhere! | Relax in Easy Elegance!
Gracious in-town apartment feels like home: living room, dining room, kitchen, 2 bedrooms, 2 baths—all just for you and your group. Quick walk to shops, restaurants, theaters, farmers’ market, and a short drive to arts offerings, hiking, skiing, swimming. Or treat yourself to a spa day at a local wellness center. Spectrum WiFi. Please note, there is no TV. Bedrooms are small but there’s plenty of space to spread out, relax, read or play games in the spacious apartment or on the shared porch.

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

Kitchenette|King Bed|Couch
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" Smart TV

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.

Bedroom Forest View I Sauna I Fire-pit I Trails
Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

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.

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.

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.

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.

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.
Popular amenities for Great Barrington holiday rentals
Other great holiday rentals in Great Barrington

Cozy. Clean. Free bagel shop.

Jug End Crest | Fireplace • Sunroom • Central Air

Stunning luxury home with fire pit

Berkshires Retreat!

Walk to Town/Lake, ’25 Renovation!

Stockbridge private apartment

A Berkshires Abode - Minutes to Ski & Downtown GB!

Hilltop Ski and Sun Chalet with Hot Tub
When is the best time to visit Great Barrington?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $340 SGD | $331 SGD | $321 SGD | $303 SGD | $326 SGD | $353 SGD | $391 SGD | $375 SGD | $336 SGD | $337 SGD | $363 SGD | $385 SGD |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Great Barrington?
Yes! Work meets play with ease at over 130 vacation rentals in Great Barrington featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Great Barrington?
Four-legged friends are welcome in Great Barrington. Choose from more than 110 vacation rentals for guests traveling with pets.
Are there Great Barrington vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Great Barrington, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in house rentals in Great Barrington?
Experience the best of Great Barrington with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly house rentals in Great Barrington?
Great Barrington has more than 120 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Great Barrington have air conditioning?
Absolutely! We offer over 120 house rentals with air conditioning in Great Barrington. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Great Barrington have wifi?
Absolutely! We offer over 40 apartment rentals with wifi in Great Barrington. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Great Barrington have a bbq area?
Absolutely! We offer over 60 house rentals with a bbq area in Great Barrington. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Great Barrington have a gym?
Absolutely! We offer over 10 house rentals with a gym in Great Barrington. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Great Barrington?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 40 homes with wifi, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Great Barrington

Total holiday rentals
Explore 220 holiday rentals in Great Barrington

Nightly prices starting at
Great Barrington holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 11,790 verified reviews to help you choose

Family-friendly holiday rentals
160 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 110 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
130 properties have a dedicated workspace

Wifi availability
220 of Great Barrington holiday rentals include wifi 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!
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- Pet-friendly rentals Great Barrington
- Rentals with a firepit Great Barrington
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- House rentals Great Barrington
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- Family-friendly rentals Great Barrington
- Rentals with a kayak Great Barrington
- Rentals with a washing machine and dryer Great Barrington
- Rentals with a fireplace Great Barrington
- Rentals with lake access Great Barrington
- Rentals with a hot tub Great Barrington
- Waterfront rentals Great Barrington
- Rentals with pools Great Barrington
- Fitness-friendly rentals Great Barrington
- Flat rentals Great Barrington
- Rentals with a patio Great Barrington
- Hunter Mountain
- Six Flags New England
- Thunder Ridge Ski Area
- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Windham Mountain
- Thacher State Park
- Butternut Ski Area and Tubing Center
- Hunter Mountain Resort
- Bash Bish Falls State Park
- Bousquet Mountain Ski Area
- Kent Falls State Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Taconic State Park
- Mount Southington Ski Area
- Ski Sundown
- Norman Rockwell Museum
- Opus 40
- Naumkeag
- Berkshire Botanical Garden
- June Farms
- Hancock Shaker Village
- Walkway Over the Hudson State Historic Park




