Hot Great Barrington Chalet Rates

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Chalets in Great Barrington

Little Longbow Lakefront Chalet

Little Longbow Lakefront Chalet

Becket
A stay at this chalet places you in the heart of Becket, within a 5-minute drive of Pyramid Lake and Jacob's Pillow.
Little Longbow Lakefront Chalet
Berkshires Hilltop Retreat w Magic View! Peak Fall Foliage Weekends Available!

Berkshires Hilltop Retreat w Magic View! Peak Fall Foliage Weekends Available!

Monterey
Located in Monterey, this chalet is on a lake, within a 10-minute drive of Beartown State Forest and Bidwell House Museum.
Berkshires Hilltop Retreat w Magic View! Peak Fall Foliage Weekends Available!
Majestic Lake Front Chalet

Majestic Lake Front Chalet

2 out of 5
Valatie
Located in Valatie, this chalet is a 5-minute drive from Kinderhook Lake and 5 minutes from Valatie Family Care.
Majestic Lake Front Chalet
Save an average of 15% on thousands of hotels when you're signed in
SRC-Hudson Valley/Berkshires Cultural Corridor

SRC-Hudson Valley/Berkshires Cultural Corridor

Canaan
Located in Canaan, this chalet is in the mountains, a 5-minute drive from Queechy Lake and 8 minutes from Furnace Brook Winery at Hilltop Orchards.
SRC-Hudson Valley/Berkshires Cultural Corridor
Don't see what you're looking for?
See all available properties in Great Barrington
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Great Barrington Chalet Accommodation

We see you over there, so lost in your own thoughts, you might miss your next meeting. You know it’s time to up your holiday game, and we know you’ve been googling things like “ski holidays” and “mountain retreats”. Don’t worry—we won’t tell your boss. We just have a tip for you: If you really want to slay, you need a chalet. Specifically, cheap chalet accommodation in Great Barrington.

A budget chalet hotel in Great Barrington is the perfect new topic for your office chit-chat, but unlike that office retreat, there will be no trust falls. You will find all sorts of adventurous activities on offer in Great Barrington, but none of them will involve your coworkers having to catch you (at least we hope not). Outside, nature awaits, with endless trails and endless fun. Inside, you’ll find all the right amenities for recharging after an active day, from luxurious linens to fully equipped kitchens.

Speaking of kitchens, chalet hotels in Great Barrington have everything you need for a romantic getaway. Cook up a candlelit dinner and open that perfectly chilled bottle of red. A crackling fireplace and the amazing views of Great Barrington out your picture window will do the rest.

Our deals practically move mountains, bringing cheap ski chalets and more to you right where you sit. Yes, you’ll have to pack eventually, but for now, browse our sweet selection of Great Barrington chalets and start dreaming. After all, didn’t your mum always tell you that you can be anything you want to be? Well, you want to be on holiday in Great Barrington, and it’s time to make it happen.

Great Barrington Chalets essential information

Accommodation
5 Chalets
Lowest Price
AU$114
Highest Price
AU$261
Popular accommodation
Little Longbow Lakefront Chalet, Berkshires Hilltop Retreat w Magic View! Peak Fall Foliage Weekends Available!, Majestic Lake Front Chalet , SRC-Hudson Valley/Berkshires Cultural Corridor

Top trending hotels in Great Barrington

Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is AU$122 per night from 5 Dec to 6 Dec
AU$122
includes taxes & fees
5 Dec - 6 Dec
With a stay at Quality Inn in Great Barrington, you'll be near ski lifts, just a 4-minute walk from Mahaiwe Performing Arts Center and 7 minutes by foot from ...
Quality Inn
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel

2.5 out of 5
415 Stockbridge Rd, Great Barrington, MA
Fully refundable
The price is AU$202 per night from 3 Dec to 4 Dec
AU$202
includes taxes & fees
3 Dec - 4 Dec
With a stay at Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel in Great Barrington, you'll be on a river, just steps from Housatonic River ...
Holiday Inn Express Hotel & Suites Great Barrington, an IHG Hotel
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 out of 5
249 Stockbridge Rd, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is AU$261 per night from 24 Nov to 25 Nov
AU$261
includes taxes & fees
24 Nov - 25 Nov
A stay at Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires places you in the heart of Great Barrington, within a 5-minute drive of Housatonic ...
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Save an average of 15% on thousands of hotels when you're signed in
Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is AU$114 per night from 24 Nov to 25 Nov
AU$114
includes taxes & fees
24 Nov - 25 Nov
With a stay at Monument Mountain Motel in Great Barrington, you'll be a 4-minute walk from Housatonic River and within a 5-minute drive of Housatonic River ...
Monument Mountain Motel
Don't see what you're looking for?
See all available properties in Great Barrington
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.