Vacation rentals in the Berkshires make for a memorable Berkshire vacation. Stay at one of the many vacation home rentals throughout the Berkshires. From vacation homes for rent to vacation apartment and condo rentals, each vacation rental offers a truly unique lodging experience. View our map to find vacation home rentals in the Northern Berkshires, Central Berkshires and Southern Berkshires. Many vacation rentals are located within a short distance to one of our wonderful Berkshire attractions such as Tanglewood, MASS MoCA, The Colonial Theatre, Norman Rockwell Museum, Barrington Stage Company, Williamstown Theatre Festival, Clark Art, Ski Areas, Colleges and more.

Vacationing In The Berkshires, Berkshire Vacations, Vacationing In Berkshire County, Vacations Berkshires

Northern Berkshires

Vacationing In The Berkshires, Berkshire Vacations, Vacationing In Berkshire County, Vacations Berkshires

Central Berkshires

Vacationing In The Berkshires, Berkshire Vacations, Vacationing In Berkshire County, Vacations Berkshires

Southern Berkshires

Adams, MA
Cozy Family Friendly Home In The Heart Of The Berkshires
2 Bedrooms, 1.5 Baths, Sleeps 6
Adams, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Berkshires Gem – Walk To Town And Trails!
4 Bedrooms, 2 Baths, Sleeps 8
Adams, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Alford, MA
NEW: Gorgeous, Unique, Craftsman Cottage
2 Bedrooms, 2 Baths, Sleeps 4
Alford, MA
Southern Berkshires
Vacation Home Rental Rates & Information

Beautiful Berkshire Farm House On 160+ Acres
7 Bedrooms, 4.5 Baths, Sleeps 16
Alford, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Berkshire Chalet Getaway!
3 Bedrooms, 2 Baths, Sleeps 6
Alford, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Becket, MA
A-Frame in Sherwood Forest
1 Bedrooms, 1 Bath, Sleeps 5
Becket, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Peace And Quiet At Sea
2 Bedrooms, 2 Bath, Sleeps 6
Becket, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Pristine Home In Becket Woods
3 Bedrooms, 2 Bath, Sleeps 6
Becket, MA
Central Berkshires
Vacation Home Rental Rates & Information

Charlemont, MA
Hidden Gem At Base Of Ski Mountain
2 Bedrooms, 1 Bath, Sleeps 6
Charlemont, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

StrautmanHaus – All-Season Chalet At Berkshire East
4 Bedrooms, 2 Bath, Sleeps 10
Charlemont, MA
Northern Berkshires
Vacation Home Rental Rates & Information

Charming 2022 Renovated 1867 Farmhouse
4 Bedrooms, 2 Bath, Sleeps 8
Charlemont, MA
NorthernBerkshires
Vacation Home Rental Rates & Information

Cheshire, MA
Ski At 19th C. Renovated Barn In The Berkshires
3 Bedrooms, 2 Bath, Sleeps 10
Cheshire, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Luxury Private Lakefront In The Berkshires
4 Bedrooms, 2.5 Bath, Sleeps 8
Cheshire, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Egremont, MA
Comfortable, Newly Renovated 2BR
Apartment
2 Bedrooms, 2 Bath, Sleeps 4
Egremont, MA
Southern Berkshires
No Pet
Vacation Home Rental Rates & Information

Charming Cottage w/ Sauna
2 Bedrooms, 1.5 Bath, Sleeps 4
Egremont, MA
Southern Berkshires
Vacation Home Rental Rates & Information

Private Berkshires Retreat
4 Bedrooms, 2.5 Bath, Sleeps 8
Egremont, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Great Barrington, MA
Ranch On 5+ Acres & 0.7 Mi To GB Main St.
3 Bedrooms, 2 Bath, Sleeps 10
Great Barrington, MA
Southern Berkshires
Vacation Home Rental Rates & Information

14 Min To Butternut, Great Barrington Guest Cottage
3 Bedrooms, 1.5 Bath, Sleeps 5
Great Barrington, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Family Home w/Big Yard On The Hill
4 Bedrooms, 2Bath, Sleeps 10
Great Barrington, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

New Remodeled 3BR Country Castle
3 Bedrooms, 3 Bath, Sleeps 8
Great Barrington, MA
Southern Berkshires
Vacation Home Rental Rates & Information

Great Barrington Getaway: Lake Access
3 Bedrooms, 2.5 Bath, Sleeps 6Great Barrington, MA
Southern Berkshires
Vacation Home Rental Rates & Information

Lakefront Berkshires Retreat w/Deck, Dock & Boat!
4 Bedrooms, 2 Bath, Sleeps 10
Great Barrington, MA
Southern Berkshires
Vacation Home Rental Rates & Information

Modern Victorian, Walk To Town
4 Bedrooms, 3 Bath, Sleeps 8
Great Barrington, MA
Southern Berkshires
Vacation Home Rental Rates & Information

Chic Updated Downtown Great Barrington
3 Bedrooms, 2.5 Bath, Sleeps 14
Great Barrington, MA
Southern Berkshires
Vacation Home Rental Rates & Information

Romantic Berkshires Cottage – Stunning Views, Pool
1 Bedrooms, 1 Bath, Sleeps 3
Great Barrington, MA
Southern Berkshires
Vacation Home Rental Rates & Information

Hancock, MA
Mountain View Suite
1 Bedrooms, 1 Bath, Sleeps 4
Hancock, MA
Northern Berkshires
Vacation Home Rental Rates & Information

1st Floor Mountain View Suite
1 Bedrooms, 1 Bath, Sleeps 4
Hancock, MA
Northern Berkshires
Vacation Home Rental Rates & Information

Quiet & Private, Small Horse Farm
1 Bedrooms, 1 Bath, Sleeps 4
Hancock, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Hawley, MA
Country Home w/Babbling Brook And Pond View
3 Bedrooms, 1 Bath, Sleeps 8
Northern, MA
Central Berkshires
Vacation Home Rental Rates & Information

Country Home w/Babbling Brook
3 Bedrooms, 1.5 Bath, Sleeps 8
Hawley, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Stunning Mountain Top Lodge
7 Bedrooms, 3.5 Bath, Sleeps 10
Hawley, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Hinsdale, MA
Ashmere Lake Log Cabin w/Privacy
2 Bedrooms, 1 Bath, Sleeps 4
Hinsdale, MA
Central Berkshires
Vacation Home Rental Rates & Information

Quiet Lake House w/Beautiful Water Views
2 Bedrooms, 2 Bath, Sleeps 8
Hinsdale, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Private Lake Front Beach In The Berkshires
3 Bedrooms, 4 Bath, Sleeps 8
Hinsdale, MA
Central Berkshires
Vacation Home Rental Rates & Information

Lanesborough, MA
Berkshire Village Carriage House
1 Bedrooms, 1 Bath, Sleeps 2
Lanesborough, MA
Central Berkshires
Vacation Home Rental Rates & Information

Charming Historic Cottage On Scenic Road To Mt. Greylock
2 Bedrooms, 1 Bath, Sleeps 6
Lanesborough, MA
Central Berkshires
Vacation Home Rental Rates & Information

NEW! Spacious Mtn Home, 5 Miles To Jiminy Peak!
3 Bedrooms, 2 Bath, Sleeps 6
Lanesborough, MA
Central Berkshires
Vacation Home Rental Rates & Information

A Beautiful Log Cabin In The Woods
2 Bedrooms, 1 Bath, Sleeps 5
Lanesborough, MA
Central Berkshires
Vacation Home Rental Rates & Information

Berkshire Pontoosuc Lake Beauty
5 Bedrooms, 3.5 Bath, Sleeps 14
Lanesborough, MA
Central Berkshires
Vacation Home Rental Rates & Information

Wildlife Cottage By The Lake
3 Bedrooms, 1.5 Bath, Sleeps 6
Lanesborough, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Berkshire Lake House Vacation Rental
4 Bedrooms, 2 Bath, Sleeps 6
Lanesborough, MA
Central Berkshires
Vacation Home Rental Rates & Information

6BR Berkshire Bliss, 38 Acres Of Nature
6 Bedrooms, 4.5 Bath, Sleeps 14
Lanesborough, MA
Central Berkshires
Vacation Home Rental Rates & Information

Lee, MA
Gorgeous, Private, Family-Friendly, Organic Home
3 Bedrooms, 2 Bath, Sleeps 6
Lee, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Spacious Berkshire Home – Year Round Retreat
5 Bedrooms, 2.5 Bath, Sleeps 12
Lee, MA
Southern Berkshires
Vacation Home Rental Rates & Information

The Playhouse: 7,000 Sq. Ft. Of Berkshires
6 Bedrooms, 5 Bath, Sleeps 20
Lee, MA
Southern Berkshires
Vacation Home Rental Rates & Information

Lenox, MA
Heart Of Lenox, Walk To Town, Cozy Cottage!
2 Bedrooms, 1 Bath, Sleeps 4
Lenox, MA
Central Berkshires
Vacation Home Rental Rates & Information

Vacation Or Work Away From Home!
2 Bedrooms, 1.5 Bath, Sleeps 5
Lenox, MA
Central Berkshires
Vacation Home Rental Rates & Information

5 Star Casual Elegance For 5 Star Guests
3 Bedrooms, 2.5 Bath, Sleeps 6
Lenox, MA
Central Berkshires
Vacation Home Rental Rates & Information

Large Lenox Home w/Pool; Ideal Berkshire Location!
4 Bedrooms, 2.5 Bath, Sleeps 8
Lenox, MA
Central Berkshires
Vacation Home Rental Rates & Information

Beautiful Lenox Home, 3 Mi To Shakespeare & Co!
3 Bedrooms, 2 Bath, Sleeps 6
Lenox, MA
Central Berkshires
Vacation Home Rental Rates & Information

Private Guest House In Dtwn Lenox, Walk To Dining!
3 Bedrooms, 2.5 Bath, Sleeps 6
Lenox, MA
Central Berkshires
Vacation Home Rental Rates & Information

Private Access To Laurel Lake – Winter Sports Fun!
4 Bedrooms, 2 Bath, Sleeps 10
Lenox, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Lovely Home In Heart Of Lenox 
2 Bedrooms, 2 Bath, Sleeps 4
Lenox, MA
Central Berkshires
Vacation Home Rental Rates & Information

Middlefield, MA
Sunny, Stylish Berkshire Mountain Retreat
4 Bedrooms, 2 Bath, Sleeps 8
Middlefield, MA
Central Berkshires
Vacation Home Rental Rates & Information

Monterey, MA
Cozy Monterey Family Chalet
2 Bedrooms, 1 Bath, Sleeps 6
Monterey, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Country Cottage For 2 On Private Setting
1 Bedrooms, 1 Bath, Sleeps 2
Southern, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Stunning Lakefront Berkshire Rental, Lake Garfield
5 Bedrooms, 2 Bath, Sleeps 8
Southern, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

New Marlborough, MA
Private Rustic Cottage w/Lake Access
2 Bedrooms, 1 Bath, Sleeps 6
New Marlborough, MA
Southern Berkshires
Vacation Home Rental Rates & Information

The Mill River Cabin w/ Fireplace & River View!
2 Bedrooms, 1 Bath, Sleeps 5
New Marlborough, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Perfect Vacation Get Away
1 Bedrooms, 1 Bath, Sleeps 4
New Marlborough, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

North Adams, MA
Lovley, Romantic, Fun, En Suite
1 Bedrooms, 1 Bath, Sleeps 4
North Adams, MA
Northern Berkshires
Vacation Home Rental Rates & Information

Beautiful Berkshire Lakeside Home
3 Bedrooms, 1.5 Bath, Sleeps 8
North Adams, MA
Northern Berkshires
Vacation Home Rental Rates & Information

Art House! Spacious Getaway By Mass Moca
6 Bedrooms, 2 Bath, Sleeps 10
North Adams, MA
Northern Berkshires
Vacation Home Rental Rates & Information

Otis, MA
The Meadows House
1 Bedrooms, 1 Bath, Sleeps 7
Otis, MA
Southern Berkshires
Vacation Home Rental Rates & Information

4BR/3BA Lakefront/Ski House In Berkshires
4 Bedrooms, 3 Bath, Sleeps 10
Otis, MA
Southern Berkshires
Vacation Home Rental Rates & Information

NEW! Berkshires Cabin 2 Mi To Appalachian Trail!
3 Bedrooms, 2 Bath, Sleeps 7
Otis, MA
Southern Berkshires
Vacation Home Rental Rates & Information

Pittsfield, MA
Lovely Family Retreat In The ♥️ Of The Berkshires!
4 Bedrooms, 2 Bath, Sleeps 7
Pittsfield, MA
Central Berkshires
Vacation Home Rental Rates & Information

Berkshire Pontoosuc Lake Beauty
5 Bedrooms, 3.5 Bath, Sleeps 14
Pittsfield, MA
Central Berkshires
Vacation Home Rental Rates & Information

Dancing Horse Lodge
3 Bedrooms, 1 Bath, Sleeps 6
Pittsfield, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Chic Pittsfield Home With A View!
3 Bedrooms, 1.5 Bath, Sleeps 6
Pittsfield, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Tranquil Lake House Getaway On Onota Lake
5 Bedrooms, 2Bath, Sleeps 11
Pittsfield, MA
Central Berkshires
Vacation Home Rental Rates & Information

Peru, MA
Swiss Chalet Style Timber Frame Home
3 Bedrooms, 2 Bath, Sleeps 6
Peru, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Remote & Relaxing Cabin In The Berkshires
3 Bedrooms, 2 Bath, Sleeps 8
Peru, MA
Central Berkshires
Vacation Home Rental Rates & Information

The Perfect Escape
3 Bedrooms, 2 Bath, Sleeps 8
Peru, MA
Central Berkshires
Vacation Home Rental Rates & Information

Richmond, MA
Spacious Berkshire Summer Rental
3 Bedrooms, 3 Bath, Sleeps 7
Richmond, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Private Apartment In Beautiful Country Barn
1 Bedrooms, 1 Bath, Sleeps 4
Richmond, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Relaxing Getaway In The Beautiful Berkshires
4 Bedrooms, 2.5 Bath, Sleeps 12
Richmond, MA
Central Berkshires
Vacation Home Rental Rates & Information

Sandisfield, MA
Sweet Dreams Retreat
1 Bedrooms, 1 Bath, Sleeps 3
Sandisfield, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Cabin With 3 Acres
4 Bedrooms, 3 Bath, Sleeps 10
Sandisfield, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Iconic Cabin In The Berkshires
6 Bedrooms, 3.5 Bath, Sleeps 12
Sandisfield, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Savoy, MA
Retreat In The Woods
2 Bedrooms, 1 Bath, Sleeps 4
Savoy, MA
Northern Berkshires
Vacation Home Rental Rates & Information

Sheffield, MA
Elterwater–Your lakefront Oasis
2 Bedrooms, 2 Bath, Sleeps 4
Sheffield, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Cheerful 3BR Cottage With Woodstove
3 Bedrooms, 2.5 Bath, Sleeps 8
Sheffield, MA
Southern Berkshires
Vacation Home Rental Rates & Information

NEW! Waterfront Sheffield Escape
3 Bedrooms, 2 Bath, Sleeps 6
Sheffield, MA
Southern Berkshires
Vacation Home Rental Rates & Information

South Lee, MA
Villa w/Access To Amazing Amenities!
2 Bedrooms, 2 Bath, Sleeps 6
South Lee, MA
Southern Berkshires
Vacation Home Rental Rates & Information

Architect Designed Home
4 Bedrooms, 3 Bath, Sleeps 8
South Lee, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Stockbridge, MA
Location!!! Location!!! Berkshire Glamour
4 Bedrooms, 3 Bath, Sleeps 8
Stockbridge, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Stockbridge Cape Near Tanglewood
4 Bedrooms, 2 Bath, Sleeps 7
Stockbridge, MA
Southern Berkshires
Vacation Home Rental Rates & Information

Stockbridge Home, Come Experience The Berkshires!
3 Bedrooms, 2 Bath, Sleeps 6
Stockbridge, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Washington, MA
Berkshires Log Cabin, Peace & Tranquility Awaits
3 Bedrooms, 1 Bath, Sleeps 8
Washington, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Beautiful Timber Frame Home
2 Bedrooms, 1 Bath, Sleeps 6
Washington, MA
Southern Berkshires
Vacation Home Rental Rates & Information

Tranquil Washington Home w/Sauna, On 70 Acres
3 Bedrooms, 2 Bath, Sleeps 6
Washington, MA
Southern Berkshires
Vacation Home Rental Rates & Information

West Stockbridge, MA
Charming Unique Cottage Relax & Enjoy
2 Bedrooms, 1 Bath, Sleeps 5
West Stockbridge, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Gorgeous Home, Nature Lover’s Delight
4 Bedrooms, 4 Bath, Sleeps 8
West Stockbridge, MA
Southern Berkshires
Vacation Home Rental Rates & Information

Sweet Escape w/Indoor Pool 
4 Bedrooms, 4 Bath, Sleeps 7
West Stockbridge, MA
Southern Berkshires
Vacation Home Rental Rates & Information

Williamstown, MA
Charming Downtown Williamstown Cottage
3 Bedrooms, 2 Bath, Sleeps 7
Williamstown, MA
Northern Berkshires
Vacation Home Rental Rates & Information

North Getaway Cottage
4 Bedrooms, 2 Bath, Sleeps 7
Williamstown, MA
Northern Berkshires
Vacation Home Rental Rates & Information

Cozy & Quaint Country Cottage
2 Bedrooms, 1 Bath, Sleeps 4
Williamstown, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Huge Luxe Williamstown Updated Victorian
5 Bedrooms, 5.5 Bath, Sleeps 10
Williamstown, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information