Great Barrington Vacation Rentals
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58 rentals in Great Barrington.
Simple living, Ranch on 5+ acres & 0.7 mi to Great Barrington. Sleeps 10 + Wi-Fi
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful House In The Woods, Huge Yard, Hot Tub
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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A perfect getaway year-round. Booking for the rest of '23 and through '24!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Peaceful Retreat Compound 10 Minutes to Great Barrington!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Historic 4-bedroom riverside home in Berkshires
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Home in Great Barrington
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Modern Victorian Walk to Town
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stay in Town, Enjoy Late Check Out
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Great Escape Ski Cottage w/HOT TUB * Great Barrington
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Great escape Barrington
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Minutes from Ski Butternut, Tanglewood, and Downtown Great Barrington
Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 15
Match: Sleeps
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Great Barrington, Cabin Sleeps 14, Walk To Town
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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In-town studio apartment. Great base for a Berkshire visit!
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Charming Cabin On Scenic Road
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Serene Renovated Barn w/ Firepit
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Romantic Berkshires Cottage - Stunning Views, Pool
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Apartment in Gorgeous Stonybrook Farm
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Evergreen: quiet cottage in Great Barrington
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Eastbungalow
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Lake Community - Near Town, Attractions
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Best of the Berkshires + Hot Tub!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Berkshire Mountain Cottage: in the Heart of the Berkshires
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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2 bedroom Riverhouse in the Heart of the Berkshires
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Great Barrington Guest House, Newly Renovated!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Modern Riverside Cottage in Hip Walkable Community
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Idyllic Berkshire Get Away: Balance of relaxation and convenience
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Great Barrington Farmhouse near Lake Mansfield
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Renovated Downtown Great Barrington House
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Great Barrington Walkable To Lake And Town!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Elegant Lake Buel Home
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Recently Renovated, steps to Lake Buel, close to Great Barrington & Stockbridge
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mason's Lodge · Luxury Home - 3 Fireplaces Mins to Ski & Town
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Remodeled ski and summer retreat close to town
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Great Barrington Home ~ 1 Mi to Ski Resort!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Classic Berkshires cottage in sun-drenched meadow
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Private Berkshires Getaway Minutes to Ski Butternut
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Minutes from downtown Great Barrington, Convenient location
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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MacMountain House: Berkshire family retreat
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Twin Maple Farm: Charming Modern Farmhouse
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Berkshire's lakefront home with deck, dock + boat
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Location Location! Comfort and Privacy So Close to Downtown
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Family vacation home in Great Barrington
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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A spacious Log Home on 11+ Acres of Private Forest 5 minutes from Ski Butternut
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Walk To Town or Hang By The Pool
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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A Fun Farmhouse Near Ski Butternut
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Berkshires Chic & Cozy, Historic Home Sleeps 10
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Classic Antique Berkshire Farmhouse with heated pool and modern amenities.
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Pretty Farmhouse w/ AGA Cooker - 2 Master Suites - 3 Miles to Great Barrington
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Showing results 1-50 of 58
Frequently Asked Questions about Great Barrington
- Yes, here are some popular vacation rentals in Great Barrington that have a pool:
- Simple living, Ranch on 5+ acres & 0.7 mi to Great Barrington. Sleeps 10 + Wi-Fi
- NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
- Beautiful House In The Woods, Huge Yard, Hot Tub
- Yes, here are some popular vacation rentals in Great Barrington that have internet access:
- Simple living, Ranch on 5+ acres & 0.7 mi to Great Barrington. Sleeps 10 + Wi-Fi
- NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
- Beautiful House In The Woods, Huge Yard, Hot Tub
- Some of the most popular kid friendly rentals in Great Barrington are:
- Simple living, Ranch on 5+ acres & 0.7 mi to Great Barrington. Sleeps 10 + Wi-Fi
- NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
- Beautiful House In The Woods, Huge Yard, Hot Tub
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