
Apartment holiday rentals in Great Barrington
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Top-rated apartment rentals in Great Barrington
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Amenia Main St Cozy Studio
Cozy studio in well maintained house from 1900. 150 sq ft with full size bed. Unit is comfortable for one, tight for two. Right in small town of Amenia. Front porch with seats/table. Walking to food, shops, drive-in movie theatre, and rail trail. Trail is 1/4 mile from house, paved and only allows walking/biking. On trail: Arts village Wassaic (3 miles south) Millerton (8 miles north). Train to NYC is 2.5m south. Tons in area: wineries, distillery, lakes, hiking, theatre & quaint towns.

Modern Copake Falls Getaway - 8 Mins to Catamount
Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

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

Hideaway with Spectacular Berkshire Views
Located on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.

King Bed |Wi-Fi| 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 KEY FEATURES: *MCM Design * Plush King Sized Bed w/ high end Centium Satin Linens *High Speed Internet *58" TV w/ Hulu + Live

Secluded but not isolated Berkshire Retreat
1.5 bedroom 1.5 bath self contained apartment (apprx. 950 sq ft ) attached to the main house set on a secluded 5.5 acre lot 2.9 miles from downtown Great Barrington . There is a CB2 day bed in the living room that sleeps an additional 2 people comfortably. Extra charge of $25/night +tax if the extra bedroom is used in 2 person reservations. $20 extra cleaning fee for reservations of 4 or more. During heating season not suitable for children under 5 because of pellet stove. .

Serene Suite near Skiing, Walk to Restaurants
Hillsdale’s Hygge Hideaway...Enjoy a peaceful, serene suite with all the comforts of home. Private entrance, with ample parking for multiple cars so you can meet up...perfectly located where the Hudson Valley meets the Berkshires. Just 8 miles east from the Taconic State Parkway, located in the center of the Historic Hamlet of Hillsdale, NY. Walk to unique shops, a cooking school, restaurants and a brewery, a full service grocery store, wine and liquor store and more.

Cosy Catskill Casita in the Middle of Village
The Casita is a studio apartment comfortable for solo travellers, couples or just two folks who don't mind sharing a bed! We’ve endeavored to make it a comfortable stay for a weekend or even longer, with all basic amenities, a queen size bed, standing shower bathroom, and kitchenette. Although it is an apartment on the ground floor of my house, you will have your privacy with a separate entrance off of the driveway which is for guest use during the stay.

Catskill Village House - The Loft
Perfect for a couple or solo traveler, The Loft is an easy and open space that evokes the playfulness and creativity of a treehouse. A cathedral ceiling, light-filled dormer, original art, and custom accents inspire the imagination. Located on the 3rd floor, the room includes a kitchenette and dining area with private bathroom and shower located at the base of the stairs. Custom queen mattress (featured at the Four Seasons NYC) organic cotton sheets.

Historical Downtown 1 Bedroom Apartment
Located in the heart of historical downtown Lenox. A beautifully renovated space fully equipped for all your needs. The eat-in kitchen has a table for two, stainless appliances, and an array of cooking essentials. The living room features a comfortable sectional and a flat screen TV for relaxing. Wi-Fi is available throughout the space. Central heat and air to provide a comfortable environment in any season. All linens and towels are provided.

Gorgeous Getaway, close to everything!
The apartment is spacious, bright, peaceful and very private. There is a coded lock, and your own front entry and spacious front porch. Located on a quiet street, just slightly off the beaten path yet within a short walk to all of the best restaurants and shopping Hudson has to offer. A full kitchen will also allow for some chill out time or a family meal if that is more your speed. A beautiful and convenient refuge.
Popular amenities for Great Barrington apartment rentals
Weekly apartment rentals

Sunny, light filled loft in 1873 Colonial

West Main

Black Cat Suites bright spacious garden suite

Cemetery Schoolhouse 2

Warren St. Ensuites - Pets allowed

Gateway to the Berkshires

Vibrant Lower Warren Street Writing Retreat

Escape to a Sleek, Serene Studio on the Riverbank
Private apartment rentals

Studio Oasis nr Warren St w porch & yard

Writer/Reader Retreat: fireplace; near skiing

Cute, Cozy and Comfortable apartment

The River’s Whisper

Center of Lenox, cozy Apartment 2-bedroom

Comfortable Pittsfield Loft

Hummingbird apt

Stockbridge private apartment
Apartment rentals with a hot tub

Esopus Creekfront Getaway | Sauna & Kayak I HotTub

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4

Ski-In Ski-Out Loft Lift & MT. Views

Cozy Ski Retreat

1 Bedroom Deluxe @ Wyndham Bentley Brook

Luxe Ski Getaway Base of Jiminy

Jiminy Peak Ski Loft with Hot Tub

Mountain Getaway Studio apt
When is the best time to visit Great Barrington?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $87 SGD | $97 SGD | $94 SGD | $111 SGD | $143 SGD | $162 SGD | $187 SGD | $196 SGD | $188 SGD | $165 SGD | $117 SGD | $108 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 |
Quick stats about flat rentals in Great Barrington

Total holiday rentals
Explore 40 holiday rentals in Great Barrington

Nightly prices starting at
Great Barrington holiday rentals start at $89 SGD per night before taxes and fees

Verified guest reviews
Over 3,870 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Great Barrington holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Great Barrington rentals

4.8 Average rating
Great Barrington stays are highly rated by guests – averaging 4.8 out of 5!
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- Family-friendly rentals Great Barrington
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- Flat rentals Berkshire County
- Flat rentals Massachusetts
- Flat rentals United States
- Hunter Mountain
- Six Flags New England
- Thunder Ridge Ski Area
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Windham Mountain
- Catamount Mountain Ski Resort
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Kent Falls State Park
- Butternut Ski Area and Tubing Center
- Hunter Mountain Resort
- Zoom Flume
- Mohawk Mountain Ski Area
- Bousquet Mountain Ski Area
- Taconic State Park
- Mount Southington Ski Area
- Norman Rockwell Museum
- Opus 40
- Berkshire Botanical Garden
- Ski Sundown
- Naumkeag
- Hancock Shaker Village
- University of Massachusetts Amherst




