Berkshire County, MA vacation rentals

Vacation rentals in Berkshire County, MA

1561 available vacation rental offers

2 1
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Choose the perfect vacation accommodation
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Rating

Best Vacation rentals and Airbnb offers in Berkshire County, MA

Jiminy Peak Mountain Resort - Berkshire County, MA
8.4Very good 1931 reviews
Berkshire County, MA
2 1
$251/nighttotal: $502 (2 )

Jiminy Peak Mountain Resort

resort
Hancock
Cozy Home Located In The Berkshires! Pet Friendly With Fenced Yard. - Berkshire County, MA
10Excellent 180 reviews
Berkshire County, MA
2 2
$329/nighttotal: $658 (2 )

Cozy Home Located In The Berkshires! Pet Friendly With Fenced Yard.

house
Adams
Vacation Village In The Berkshires - Berkshire County, MA
8.6Very good 2753 reviews
Berkshire County, MA
2 1
$256/nighttotal: $512 (2 )

Vacation Village In The Berkshires

resort
Hancock
Cozy Apartment Near Jiminy Peak - Berkshire County, MA
9.7Excellent 151 reviews
Berkshire County, MA
2 2
$129/nighttotal: $258 (2 )

Cozy Apartment Near Jiminy Peak

Hancock
Barn Guesthouse W/ Pool - Berkshire County, MA
9.8Excellent 55 reviews
Berkshire County, MA
2 1
$300/nighttotal: $600 (2 )

Barn Guesthouse W/ Pool

house
New Marlborough
Cabin With Spectacular Views Of Robin Hood Lake - Berkshire County, MA
9.5Excellent 97 reviews
Berkshire County, MA
2 2
$329/nighttotal: $658 (2 )

Cabin With Spectacular Views Of Robin Hood Lake

cabin
Becket
East Otis Vacation Rental W/ Private Deck & Bbq! - Berkshire County, MA
9.3Excellent 34 reviews
Berkshire County, MA
2 1
$325/nighttotal: $650 (2 )

East Otis Vacation Rental W/ Private Deck & Bbq!

cottage
Otis
Sweet Dreams Retreat - Berkshire County, MA
9.8Excellent 122 reviews
Berkshire County, MA
2 1
$313/nighttotal: $626 (2 )

Sweet Dreams Retreat

house
Sandisfield
Hot Tub In Berkshires! 3 Queen 2 Bath! Windswept! - Berkshire County, MA
9.6Excellent 186 reviews
Berkshire County, MA
2 3
$380/nighttotal: $760 (2 )

Hot Tub In Berkshires! 3 Queen 2 Bath! Windswept!

apartment
Chatham
Quiet Rustic Cottage With Shared Lake Access - Berkshire County, MA
10Excellent 188 reviews
Berkshire County, MA
2 2
$320/nighttotal: $640 (2 )

Quiet Rustic Cottage With Shared Lake Access

cottage
New Marlborough
Cozy Guesthouse Minutes Away From Hiking! - Berkshire County, MA
9.8Excellent 177 reviews
Berkshire County, MA
2 1
$226/nighttotal: $452 (2 )

Cozy Guesthouse Minutes Away From Hiking!

house
New Marlborough
T’other House - Berkshire County, MA
9.9Excellent 167 reviews
Berkshire County, MA
2 1
$186/nighttotal: $372 (2 )

T’other House

Lenox

Best Berkshire County, MA vacation rentals with a pool

Among the 1561 accommodations in Berkshire County, MA, here are the 8 best rentals with a pool

The Ponds At Foxhollow By Capital Vacations - Berkshire County, MA
8.3Very good 238 reviews
Berkshire County, MA
2 1
$530/nighttotal: $1060 (2 )

The Ponds At Foxhollow By Capital Vacations

apartment
Lenox
Star Gazer Farm - Berkshire County, MA
9.8Excellent 18 reviews
Berkshire County, MA
2 1
$281/nighttotal: $562 (2 )

Star Gazer Farm

house
East Nassau
Berkshires Retreat In Great Barrington - Berkshire County, MA
9.8Excellent 41 reviews
Berkshire County, MA
2 1
$205/nighttotal: $410 (2 )

Berkshires Retreat In Great Barrington

Great Barrington
Vacation Village In The Berkshires - Berkshire County, MA
8.6Very good 1653 reviews
Berkshire County, MA
2 1
$319/nighttotal: $638 (2 )

Vacation Village In The Berkshires

apartment
Hancock
Deluxe Yeti Suite On Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn - Berkshire County, MA
9.7Excellent 32 reviews
Berkshire County, MA
2 1
$416/nighttotal: $832 (2 )

Deluxe Yeti Suite On Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

apartment
Hancock
Mountain Retreat - Deluxe 1 Bedroom Condo - Berkshire County, MA
10Excellent 6 reviews
Berkshire County, MA
2 1
$681/nighttotal: $1362 (2 )

Mountain Retreat - Deluxe 1 Bedroom Condo

apartment
Hancock
Unique - 1br Country Condo @ Jiminy Peak - Berkshire County, MA
10Excellent 14 reviews
Berkshire County, MA
2 1
$466/nighttotal: $932 (2 )

Unique - 1br Country Condo @ Jiminy Peak

apartment
Hancock
Family-friendly Hancock Home Walk To Slopes! - Berkshire County, MA
9.9Excellent 18 reviews
Berkshire County, MA
2 4
$1179/nighttotal: $2358 (2 )

Family-friendly Hancock Home Walk To Slopes!

house
Hancock

Top cities

Best family friendly Berkshire County, MA vacation rentals

Among the 1561 accommodations in Berkshire County, MA, here are the 8 best family friendly rentals

Fall/winter Spa Nature Sanctuary - Berkshire County, MA
9.7Excellent 62 reviews
Berkshire County, MA
2 3
$436/nighttotal: $872 (2 )

Fall/winter Spa Nature Sanctuary

Mount Washington
Perfect Vacation Get Away - Historical New Marlborough - Berkshire County, MA
9.4Excellent 49 reviews
Berkshire County, MA
2 1
$341/nighttotal: $682 (2 )

Perfect Vacation Get Away - Historical New Marlborough

cottage
New Marlborough
Quiet, One Bedroom Suite; 1.5 Miles To Jiminy Peak - Berkshire County, MA
10Excellent 57 reviews
Berkshire County, MA
2 1
$434/nighttotal: $868 (2 )

Quiet, One Bedroom Suite; 1.5 Miles To Jiminy Peak

gîte
Hancock
Wow! Best Berkshire Snowhome #1 Private Superclean - Berkshire County, MA
9.8Excellent 106 reviews
Berkshire County, MA
2 2
$268/nighttotal: $536 (2 )

Wow! Best Berkshire Snowhome #1 Private Superclean

apartment
Sheffield
Beautiful, Quiet And Cozy Home In Becket! - Berkshire County, MA
9.8Excellent 92 reviews
Berkshire County, MA
2 3
$294/nighttotal: $588 (2 )

Beautiful, Quiet And Cozy Home In Becket!

Becket
Charming/rustic Apartment With Downtown Views - Berkshire County, MA
10Excellent 47 reviews
Berkshire County, MA
2 1
$194/nighttotal: $388 (2 )

Charming/rustic Apartment With Downtown Views

apartment
Adams
5 Minutes From Catamount Ski Area - Berkshire County, MA
9.2Excellent 60 reviews
Berkshire County, MA
2 4
$362/nighttotal: $724 (2 )

5 Minutes From Catamount Ski Area

house
Egremont
Berkshires House With Fire Pit -Relax, Ski, Kayak - Berkshire County, MA
9.8Excellent 75 reviews
Berkshire County, MA
2 2
$238/nighttotal: $476 (2 )

Berkshires House With Fire Pit -Relax, Ski, Kayak

cottage
Florida

Frequently asked questions for the vacation rentals in Berkshire County, MA

Popular regions

Best pet friendly Berkshire County, MA vacation rentals

Among the 1561 accommodations in Berkshire County, MA, here are the 7 best pet friendly rentals

River Forest House - Berkshire County, MA
9.5Excellent 83 reviews
Berkshire County, MA
2 3
$472/nighttotal: $944 (2 )

River Forest House

apartment
Cummington
The Wampanoag Cabin @ The Wigwam Western Summit - Berkshire County, MA
9.9Excellent 143 reviews
Berkshire County, MA
2 1
$294/nighttotal: $588 (2 )

The Wampanoag Cabin @ The Wigwam Western Summit

cabin
North Adams
Mountainside Condo @ Jiminy Peak In The Berkshires - Berkshire County, MA
10Excellent 91 reviews
Berkshire County, MA
2 2
$385/nighttotal: $770 (2 )

Mountainside Condo @ Jiminy Peak In The Berkshires

apartment
Hancock
Double 3 Bedroom Tree House In The Berkshires - Berkshire County, MA
9.8Excellent 82 reviews
Berkshire County, MA
2 3
$256/nighttotal: $512 (2 )

Double 3 Bedroom Tree House In The Berkshires

cabin
New Marlborough
Enjoy Every Season The Berkshires Have To Offer. - Berkshire County, MA
10Excellent 59 reviews
Berkshire County, MA
2 1
$186/nighttotal: $372 (2 )

Enjoy Every Season The Berkshires Have To Offer.

apartment
Otis
Disney Magic Suite At Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat - Berkshire County, MA
9.8Excellent 28 reviews
Berkshire County, MA
2 1
$416/nighttotal: $832 (2 )

Disney Magic Suite At Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

apartment
Hancock
Gorgeous Zen Must-see Suite At Jiminy Country Inn - Sleeps 4 Ski On/off At Mtn - Berkshire County, MA
9.3Excellent 28 reviews
Berkshire County, MA
2 1
$478/nighttotal: $956 (2 )

Gorgeous Zen Must-see Suite At Jiminy Country Inn - Sleeps 4 Ski On/off At Mtn

apartment
Hancock

Neighborhoods and points of interest in Berkshire County, MA