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Cottages, Villas, Apartments in Great Barrington
Holiday Rentals
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Massachusetts (MA)
Berkshires
Cottages, Villas, Apartments in Great Barrington
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Internet or Wifi (78)
Air Conditioning (75)
Washer/Dryer (73)
Grill (69)
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Suitability
Kid friendly (75)
Pet friendly (39)
Wheelchair access (0)
Elder access (0)
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Holiday Rental House (72)
Condominium/Apartment (7)
Cabin Holiday Rental (0)
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Waterfront (5)
Boat Available (3)
Private Chef (0)
Private Beach (0)
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Distance from
5 mi
Monument Mountain
Mahaiwe Performing Arts Center
Ski Butternut
The Guthrie Center & Foundation
Housatonic River Walk
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79 rentals
in Great Barrington.
Butternut SKI 4miles!! Ranch Sleeps 10 & 0.7 mi to GB Main St.Wi-Fi + HOT TUB.
19
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
12
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Beautiful House In The Woods, Huge Yard, Hot Tub
10
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
5 BD, 3 Baths, sleeps 12 - the pool is open & a few openings for Summer 2024 !
118
Holiday Rental House
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6 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
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As seen on
Peaceful Retreat Compound 10 Minutes to Great Barrington!
20
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 12
Match:
Sleeps
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As seen on
Home in Great Barrington
10
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps
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As seen on
Modern Victorian Walk to Town / Close to 2 Ski Resorts!
10
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
An In-Town Beauty with Late Checkout
13
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
The Great Escape Ski Cottage w/HOT TUB * Great Barrington
15
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 16
Match:
Sleeps
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As seen on
Stunning Renovated Victorian
10
Holiday Rental House
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5 bedrooms
5 bathrooms
Sleeps 12
Match:
Sleeps
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Great Barrington Get Away
2
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington
18
Holiday Rental House
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7 bedrooms
7 bathrooms
Sleeps 15
Match:
Sleeps
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As seen on
Great Barrington, Cabin Sleeps 14, Walk To Town
13
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 14
Match:
Sleeps
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As seen on
Charming Cabin On Scenic Road
5
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
Romantic Berkshires Cottage - Stunning Views, Pool
46
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 3
Match:
Sleeps
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As seen on
Studio Loft in the Berkshires
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Sleeps
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Apartment in Gorgeous Stonybrook Farm
41
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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As seen on
Evergreen: quiet cottage in Great Barrington
2
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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Eastbungalow
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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As seen on
Lake Community - Near Town, Attractions
37
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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As seen on
Best of the Berkshires + Hot Tub by Evergreen Home
6
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
Berkshire Mountain Cottage: in the Heart of the Berkshires
10
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
2 bedroom Riverhouse in the Heart of the Berkshires
10
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
Ski Season Rental!
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 5
Match:
Sleeps
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As seen on
Renovated Private Guest House by Evergreen Home
9
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps
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As seen on
Modern Riverside Cottage in Hip Walkable Community
2
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Great Barrington Farmhouse near Lake Mansfield
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Renovated Downtown Great Barrington House
2
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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New home in the Berkshires. Fire pit, Hot tub, gas grill, private & quiet.
2
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Great Barrington Walkable to Lake and Town!
4
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 11
Match:
Sleeps
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As seen on
Beautiful Berkshire Lake View and 2.1 Miles from Down Hill Skiing!
7
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Elegant Lake Buel Home
2
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Recently Renovated, steps to Lake Buel, close to Great Barrington & Stockbridge
12
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Mason's Lodge · Luxury Home - 3 Fireplaces Mins to Ski & Town
7
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Remodeled ski and summer retreat close to town
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Cozy Great Barrington Home ~ 1 Mi to Ski Resort!
2
Holiday Rental House
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5 bedrooms
2 bathrooms
Sleeps 9
Match:
Sleeps
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As seen on
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
7
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
Classic Berkshires cottage in sun-drenched meadow
5
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Private Berkshires Getaway Minutes to Ski Butternut
10
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Minutes from downtown Great Barrington, Convenient location
11
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Twin Maple Farm: Charming Modern Farmhouse
10
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
11
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
Location Location! Comfort and Privacy So Close to Downtown
10
Holiday Rental House
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5 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps
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As seen on
Family vacation home in Great Barrington
12
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
A spacious Log Home on 11+ Acres of Private Forest 5 minutes from Ski Butternut
5
Holiday Rental House
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5 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Hang By The Pool or Walk To Town
10
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
A Fun Farmhouse Near Ski Butternut
10
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Berkshires / Great Barrington Chic & Cozy, Sleeps 10
9
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
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Classic Antique Berkshire Farmhouse with heated pool and modern amenities.
4
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 11
Match:
Sleeps
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As seen on
Farmhouse w AGA, 2 suites - close to GB & skiing
10
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
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Showing results 1-50 of 79
Frequently Asked Questions about Great Barrington
Do any holiday rentals in Great Barrington have a pool?
Yes, here are some popular holiday rentals in Great Barrington that have a pool:
Butternut SKI 4miles!! Ranch Sleeps 10 & 0.7 mi to GB Main St.Wi-Fi + HOT TUB.
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Beautiful House In The Woods, Huge Yard, Hot Tub
See all holiday rentals with a pool in Great Barrington on Tripadvisor
Do any holiday rentals in Great Barrington have internet access?
Yes, here are some popular holiday rentals in Great Barrington that have internet access:
Butternut SKI 4miles!! Ranch Sleeps 10 & 0.7 mi to GB Main St.Wi-Fi + HOT TUB.
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Beautiful House In The Woods, Huge Yard, Hot Tub
See all holiday rentals in Great Barrington on Tripadvisor
What are the best pet friendly rentals in Great Barrington?
The best pet friendly rentals in Great Barrington are:
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Beautiful House In The Woods, Huge Yard, Hot Tub
Peaceful Retreat Compound 10 Minutes to Great Barrington!
See all pet friendly holiday rentals in Great Barrington on Tripadvisor
What are some great rentals in Great Barrington that are kid friendly?
Some of the most popular kid friendly rentals in Great Barrington are:
Butternut SKI 4miles!! Ranch Sleeps 10 & 0.7 mi to GB Main St.Wi-Fi + HOT TUB.
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Beautiful House In The Woods, Huge Yard, Hot Tub
See all kid friendly holiday rentals in Great Barrington on Tripadvisor
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