Hot Great Barrington Cottage Rates

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Featured Cottages in Great Barrington

The Blue Elm - A Historic Berkshire Cottage

The Blue Elm - A Historic Berkshire Cottage

Sheffield
The price is AU$617 per night from 23 Sept to 24 Sept
AU$617
23 Sept - 24 Sept
includes taxes & fees
Located in Ashley Falls, this cottage is in a rural location, within a 15-minute walk of Ashley Falls Woods and Housatonic River.
Opens in a new windowThe Blue Elm - A Historic Berkshire Cottage
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

2 out of 5
Canaan
Located in Canaan, this cottage is on the waterfront, a 3-minute drive from Queechy Lake and 7 minutes from Furnace Brook Winery at Hilltop Orchards.
Opens in a new windowCharming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires
Summer Lake Cottage, private beach, Berkshire Hills, small village

Summer Lake Cottage, private beach, Berkshire Hills, small village

Lakeville
Located in Lakeville, this cottage is on a lake, a 4-minute drive from Holley-Williams House Museum and 6 minutes from North East Town Hall.
Opens in a new windowSummer Lake Cottage, private beach, Berkshire Hills, small village
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Two Bedroom Cottage Close To Town

Two Bedroom Cottage Close To Town

Sharon
Located in Sharon, this cottage is a 4-minute drive from Bodhi Tree Gallery and 7 minutes from TriArts Sharon Playhouse.
Opens in a new windowTwo Bedroom Cottage Close To Town
The Cottage at Highland Lake, year-round, waterfront with a boat dock

The Cottage at Highland Lake, year-round, waterfront with a boat dock

Winsted
With a stay at this cottage in Winsted, you'll be on the waterfront, just steps from Highland Lake and a 2-minute drive from Winchester Historical Society.
Opens in a new windowThe Cottage at Highland Lake, year-round, waterfront with a boat dock
Idillic summer getaway in Litchfield Hills, CT.

Idillic summer getaway in Litchfield Hills, CT.

Sharon
When you stay at this cottage in Sharon, you'll be on a river, within a 5-minute drive of Housatonic Meadows State Park and West Cornwall Covered Bridge.
Opens in a new windowIdillic summer getaway in Litchfield Hills, CT.
Heaven Can't Wait, On Beautiful Kinderhook Lake!!

Heaven Can't Wait, On Beautiful Kinderhook Lake!!

Valatie
Located in Valatie, this cottage is on a lake, a 1-minute drive from Kinderhook Lake and 7 minutes from Valatie Free Library.
Opens in a new windowHeaven Can't Wait, On Beautiful Kinderhook Lake!!
Lakefront Tranquility/Fishermans Delight

Lakefront Tranquility/Fishermans Delight

New Hartford
Located in New Hartford, this cottage is on the waterfront, a 1-minute drive from Brodie Park and 7 minutes from New Hartford Free Public Library.
Opens in a new windowLakefront Tranquility/Fishermans Delight
Creekside Cottage The Fitz House Red Hook NY

Creekside Cottage The Fitz House Red Hook NY

Red Hook
Located in Red Hook, this cottage is on a river, within a 15-minute drive of Lake Carvel and Lake Taghkanic State Park.
Opens in a new windowCreekside Cottage The Fitz House Red Hook NY
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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 Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Great Barrington will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Great Barrington definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Great Barrington, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Great Barrington Cottages essential information

Accommodation
152 Cottages
Lowest Price
AU$156
Highest Price
AU$617
Popular accommodation
The Blue Elm - A Historic Berkshire Cottage, Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires, Summer Lake Cottage, private beach, Berkshire Hills, small village, Two Bedroom Cottage Close To Town, The Cottage at Highland Lake, year-round, waterfront with a boat dock , Idillic summer getaway in Litchfield Hills, CT., Heaven Can't Wait, On Beautiful Kinderhook Lake!!, Lakefront Tranquility/Fishermans Delight, Creekside Cottage The Fitz House Red Hook NY

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$156 per night from 5 Oct to 6 Oct
AU$156
5 Oct - 6 Oct
includes taxes & fees
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 ...
Opens in a new windowQuality Inn
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 out of 5
415 Stockbridge Rd, Great Barrington, MA
Fully refundable
The price is AU$220 per night from 22 Sept to 23 Sept
AU$220
22 Sept - 23 Sept
includes taxes & fees
With a stay at Holiday Inn Express Hotel & Suites Great Barrington by IHG in Great Barrington, you'll be on a river, just steps from Housatonic River and a 3-minute ...
Opens in a new windowHoliday Inn Express Hotel & Suites Great Barrington by IHG
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$269 per night from 23 Sept to 24 Sept
AU$269
23 Sept - 24 Sept
includes taxes & fees
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 ...
Opens in a new windowFairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
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Monument Mountain Motel

Monument Mountain Motel

2.5 out of 5
247 Stockbridge Rd, Great Barrington, MA
Fully refundableReserve now, pay when you stay
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 ...
Opens in a new windowMonument Mountain Motel
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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.

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^Subject to availability and chosen travel dates.