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.
Northern Berkshires
Central Berkshires
Southern Berkshires
Adams, MA
Berkshires Gem – Walk To Town And Trails!
4 Bedrooms, 2 Baths, Sleeps 8
Adams, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Berkshire Village Carriage House – Super Private!!
1 Bedrooms, 1 Baths, Sleeps 2
Adams, MA
Northern Berkshires
No Pets
Vacation Home Rental Rates & Information
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
Golf House By Mt Greylock – Walkable Adventures!
4 Bedrooms, 3 Baths, Sleeps 7
Adams, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Park Street Penthouse Apartment
1 Bedrooms, 1 Baths, Sleeps 4
Adams, MA
Northern Berkshires
No Pets
Vacation Home Rental Rates & Information
Alford, MA
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
NEW: Gorgeous, Unique, Craftsman Cottage
2 Bedrooms, 2 Baths, Sleeps 4
Alford, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Becket, MA
Berkshires Lakefront Retreat, Idyllic Retreat
3 Bedrooms, 2 Baths, Sleeps 8
Becket, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Lakefront Jewel, Stunning, Unparalleled Views
3 Bedrooms, 2 Baths, Sleeps 7
Becket, MA
Central Berkshires
No Pets
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
Pet Friendly
Vacation Home Rental Rates & Information
Private Lake Cottage On 3 Acres w/350 Sq. Ft. Deck
3 Bedrooms, 2 Baths, Sleeps 8
Becket, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Spring In The Berkshires! Hot Tub, Hiking, Canoe, Biking
2 Bedrooms, 1 Baths, Sleeps 7
Becket, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Charlemont, MA
Bear Creek Cabin, Tranquil Views
3 Bedrooms, 2 Baths, Sleeps 8
Charlemont, MA
Northern Berkshires
No Pets
Vacation Home Rental Rates & Information
Berkshires Getaway < 1 Mi Skiing & Hiking!
3 Bedrooms, 1.5 Baths, Sleeps 6
Charlemont, MA
Northern Berkshires
No Pets
Vacation Home Rental Rates & Information
Charming 2022 Renovated 1867 Farmhouse
4 Bedrooms, 2 Bath, Sleeps 8
Charlemont, MA
Northern Berkshires
No Pets
Vacation Home Rental Rates & Information
Hidden Gem At Base Of Ski Mountain
2 Bedrooms, 1 Bath, Sleeps 6
Charlemont, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Live History In The Restored Parsonage, Tranquil & Rejuvenating Escape
4 Bedrooms, 2 Baths, Sleeps 8
Charlemont, MA
Northern Berkshires
No Pets
Vacation Home Rental Rates & Information
Lodge Log Cabin Nestled In The Woods
4 Bedrooms, 2 Baths, Sleeps 12
Charlemont, MA
Northern Berkshires
No Pets
Vacation Home Rental Rates & Information
StrautmanHaus – All-Season Chalet At Berkshire East
4 Bedrooms, 2 Bath, Sleeps 10
Charlemont, MA
Northern Berkshires
No Pets
Vacation Home Rental Rates & Information
Cheshire, MA
Lakeside Oasis w/4 Kayaks & Charm
2 Bedrooms, 1 Baths, Sleeps 4
Cheshire, MA
Northern Berkshires
No Pets
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
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
Egremont, MA
Charming Idyllic Farmhouse
4 Bedrooms, 3 Baths, Sleeps 8
Egremont, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Comfortable, Newly Renovated 2BR
Apartment
2 Bedrooms, 2 Bath, Sleeps 4
Egremont, MA
Southern Berkshires
No Pet
Vacation Home Rental Rates & Information
Family Ski House at Catamount!
4 Bedrooms, 3 Baths, Sleeps 8
Egremont, MA
Southern Berkshires
Pet Friendly
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
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
Beautiful House In The Woods
7 Bedrooms, 6 Baths, Sleeps 15
Great Barrington, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Berkshires Summer Chalet w/Pool
4 Bedrooms, 3 Baths, Sleeps 8
Great Barrington, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Chic Updated Downtown Great Barrington
3 Bedrooms, 2.5 Bath, Sleeps 14
Great Barrington, MA
Southern Berkshires
No Pets
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
Gem Of The Berkshires, Mountain View
5 Bedrooms, 3 Baths, Sleeps 10
Great Barrington, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Great Barrington Getaway: Lake Access
3 Bedrooms, 2.5 Bath, Sleeps 6 Great Barrington, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Lakefront Berkshires Retreat w/Deck, Dock & Boat!
4 Bedrooms, 2 Bath, Sleeps 10
Great Barrington, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Modern Victorian, Walk To Town
4 Bedrooms, 3 Bath, Sleeps 8
Great Barrington, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
New Remodeled 3BR Country Castle
3 Bedrooms, 3 Bath, Sleeps 8
Great Barrington, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Premiere Berkshire Country Estate w/Private Pool
4 Bedrooms, 4 Baths, Sleeps 12
Great Barrington, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Romantic Berkshires Cottage – Stunning Views, Pool
1 Bedrooms, 1 Bath, Sleeps 3
Great Barrington, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Spectacular Views & Close To Great Barrington
3 Bedrooms, 2 Baths, Sleeps 6
Great Barrington, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Stunning Renovated Victorian
5 Bedrooms, 4.5 Baths, Sleeps 12
Great Barrington, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Sunsets On Blue Hill
4 Bedrooms, 3 Baths, Sleeps 9
Great Barrington, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
The Great Escape Ski Cottage w/Hot Tub
5 Bedrooms, 4 Baths, Sleeps 16
Great Barrington, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Hancock, MA
1st Floor Mountain View Suite
1 Bedrooms, 1 Bath, Sleeps 4
Hancock, MA
Northern Berkshires
No Pets
Vacation Home Rental Rates & Information
Mountain View Suite
1 Bedrooms, 1 Bath, Sleeps 4
Hancock, MA
Northern Berkshires
No Pets
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
No Pets
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
No Pets
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
Lanesborough, MA
6BR Berkshire Bliss, 38 Acres Of Nature
6 Bedrooms, 4.5 Bath, Sleeps 14
Lanesborough, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
A Beautiful Log Cabin In The Woods
2 Bedrooms, 1 Bath, Sleeps 5
Lanesborough, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Berkshire Lake House Vacation Rental
4 Bedrooms, 2 Bath, Sleeps 6
Lanesborough, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Berkshire Pontoosuc Lake Beauty
5 Bedrooms, 3.5 Bath, Sleeps 14
Lanesborough, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Berkshire Village Carriage House
1 Bedrooms, 1 Bath, Sleeps 2
Lanesborough, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Charming Historic Cottage On Scenic Road To Mt. Greylock
2 Bedrooms, 1 Bath, Sleeps 6
Lanesborough, MA
Central Berkshires
No Pets
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
Lee, MA
4BR Home w/Yard & BBQ
4 Bedrooms, 2 Bath, Sleeps 8
Lee, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Berkshires Home Makeover ~ Lakefront Getaway
4 Bedrooms, 6 Bath, Sleeps 8
Lee, MA
Southern Berkshires
No Pet
Vacation Home Rental Rates & Information
Berkshire House Stay
5 Bedrooms, 5.5 Bath, Sleeps 10
Lee, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Lovely Home On Golden Hill
4 Bedrooms, 4 Bath, Sleeps 10
Lee, MA
Southern Berkshires
No Pet
Vacation Home Rental Rates & Information
Private Berkshire Escape
4 Bedrooms, 2 Bath, Sleeps 10
Lee, MA
Southern Berkshires
No Pet
Vacation Home Rental Rates & Information
Spacious 5BR House In Lee
5 Bedrooms, 3.5 Bath, Sleeps 15
Lee, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Stunning Lake Views & Privacy
3 Bedrooms, 3.5 Bath, Sleeps 14
Lee, MA
Southern Berkshires
No Pet
Vacation Home Rental Rates & Information
Stunning Post & Beam Home
5 Bedrooms, 3.5 Bath, Sleeps 14
Lee, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
The Playhouse: 7,000 Sq. Ft. Of Berkshires
6 Bedrooms, 5 Bath, Sleeps 20
Lee, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Lenox, MA
5 Star Casual Elegance For 5 Star Guests
3 Bedrooms, 2.5 Bath, Sleeps 6
Lenox, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Amore Estate, 8 Acre Property
6 Bedrooms, 4 Baths, Sleeps 16
Lenox, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Beautiful Lenox Home, 3 Mi To Shakespeare & Co!
3 Bedrooms, 2 Bath, Sleeps 6
Lenox, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Chic Modern Farmhouse
4 Bedrooms, 3.5 Baths, Sleeps 8
Lenox, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Enjoy Comfortable Elegance In This Secluded Grand Home
5 Bedrooms, 2 Baths, Sleeps 9
Lenox, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Heart Of Lenox, Walk To Town, Cozy Cottage!
2 Bedrooms, 1 Bath, Sleeps 4
Lenox, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Large Lenox Home w/Pool; Ideal Berkshire Location!
4 Bedrooms, 2.5 Bath, Sleeps 8
Lenox, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Lovely Home In Heart Of Lenox
2 Bedrooms, 2 Bath, Sleeps 4
Lenox, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Luxury Berkshires Retreat – Main House & Studio
7 Bedrooms, 4.5 Baths, Sleeps 15
Lenox, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Newly Renovated Lakefront Haven
4 Bedrooms, 3 Baths, Sleeps 10
Lenox, MA
Central Berkshires
No Pets
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
Private Guest House In Dtwn Lenox, Walk To Dining!
3 Bedrooms, 2.5 Bath, Sleeps 6
Lenox, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Vacation Or Work Away From Home!
2 Bedrooms, 1.5 Bath, Sleeps 5
Lenox, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Winthrop Estate – 1925 Charm & Modern Luxury
12 Bedrooms, 10.5 Baths, Sleeps 24
Lenox, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Middlefield, MA
Sunny, Stylish Berkshire Mountain Retreat
4 Bedrooms, 2 Bath, Sleeps 8
Middlefield, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Monterey, MA
Country Cottage For 2 On Private Setting
1 Bedrooms, 1 Bath, Sleeps 2
Southern, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Cozy Monterey Family Chalet
2 Bedrooms, 1 Bath, Sleeps 6
Monterey, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Stunning Lakefront Berkshire Rental, Lake Garfield
5 Bedrooms, 2 Bath, Sleeps 8
Monterey, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
New Marlborough, MA
Perfect Vacation Get Away
1 Bedrooms, 1 Bath, Sleeps 4
New Marlborough, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Private Rustic Cottage w/Lake Access
2 Bedrooms, 1 Bath, Sleeps 6
New Marlborough, MA
Southern Berkshires
No Pets
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
North Adams, MA
Art House! Spacious Getaway By Mass Moca
6 Bedrooms, 2 Bath, Sleeps 10
North Adams, MA
Northern Berkshires
No Pets
Vacation Home Rental Rates & Information
Beautiful Berkshire Lakeside Home
3 Bedrooms, 1.5 Bath, Sleeps 8
North Adams, MA
Northern Berkshires
No Pets
Vacation Home Rental Rates & Information
Lovley, Romantic, Fun, En Suite
1 Bedrooms, 1 Bath, Sleeps 4
North Adams, MA
Northern Berkshires
No Pets
Vacation Home Rental Rates & Information
Otis, MA
4BR/3BA Lakefront/Ski House In Berkshires
4 Bedrooms, 3 Bath, Sleeps 10
Otis, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
NEW! Berkshires Cabin 2 Mi To Appalachian Trail!
3 Bedrooms, 2 Bath, Sleeps 7
Otis, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
The Meadows House
1 Bedrooms, 1 Bath, Sleeps 7
Otis, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Pittsfield, MA
Cape Home In The Beautiful Berkshires
5 Bedrooms, 2 Baths, Sleeps 10
Pittsfield, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Casa Do Lago Waterfront Home
5 Bedrooms, 3.5 Baths, Sleeps 14
Pittsfield, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Charming Historic Home
5 Bedrooms, 3.5 Bath, Sleeps 10
Pittsfield, MA
Central Berkshires
No Pets
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
Dancing Horse Lodge
3 Bedrooms, 1 Bath, Sleeps 6
Pittsfield, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Grand Berkshire Manor
5 Bedrooms, 4.5 Baths, Sleeps 10
Pittsfield, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Hidden Oasis In The Mountains
5 Bedrooms, 3 Baths, Sleeps 10
Pittsfield, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Lake Front Home In The Berkshires
4 Bedrooms, 4 Baths, Sleeps 10
Pittsfield, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Lakeside Home With Pool
6 Bedrooms, 4.5 Baths, Sleeps 16
Pittsfield, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Renovated Pittsfield Colonial
4 Bedrooms, 2.5 Baths, Sleeps 12
Pittsfield, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Slopeside View: Airy, Luxury Condo
5 Bedrooms, 4.5 Baths, Sleeps 10
Pittsfield, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Spacious Historic Home In The Berkshires!
5 Bedrooms, 2 Baths, Sleeps 9
Pittsfield, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Spacious Luxury Berkshire’s Estate
6 Bedrooms, 4.5 Baths, Sleeps 14
Pittsfield, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Peru, MA
Remote & Relaxing Cabin In The Berkshires
3 Bedrooms, 2 Bath, Sleeps 8
Peru, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Swiss Chalet Style Timber Frame Home
3 Bedrooms, 2 Bath, Sleeps 6
Peru, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
The Perfect Escape
3 Bedrooms, 2 Bath, Sleeps 8
Peru, MA
Central Berkshires
No Pets
Vacation Home Rental Rates & Information
Richmond, MA
Private Apartment In Beautiful Country Barn
1 Bedrooms, 1 Bath, Sleeps 4
Richmond, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Spacious Berkshire Summer Rental
3 Bedrooms, 3 Bath, Sleeps 7
Richmond, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Sandisfield, MA
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
Sweet Dreams Retreat
1 Bedrooms, 1 Bath, Sleeps 3
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
No Pets
Vacation Home Rental Rates & Information
Sheffield, MA
Cheerful 3BR Cottage With Woodstove
3 Bedrooms, 2.5 Bath, Sleeps 8
Sheffield, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Elterwater–Your lakefront Oasis
2 Bedrooms, 2 Bath, Sleeps 4
Sheffield, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
NEW! Waterfront Sheffield Escape
3 Bedrooms, 2 Bath, Sleeps 6
Sheffield, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
South Lee, MA
Architect Designed Home
4 Bedrooms, 3 Bath, Sleeps 8
South Lee, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Stockbridge, MA
A Grand Property In Historic Stockbridge
6 Bedrooms, 6.5.5 Baths, Sleeps 12
Stockbridge, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
General Williams Estate House
6 Bedrooms, 5.5 Baths, Sleeps 16
Stockbridge, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Historic Rectory Retreat
5 Bedrooms, 2 Baths, Sleeps 12
Stockbridge, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Historic Stockbridge Villa
11 Bedrooms, 6.5 Baths, Sleeps 23
Stockbridge, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
In-Town Victorian
12 Bedrooms, 7.5 Baths, Sleeps 24
Stockbridge, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Just A Min From Downtown Stockbridge
4 Bedrooms, 4 Baths, Sleeps 8
Stockbridge, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Location!!! Location!!! Berkshire Glamour
4 Bedrooms, 3 Bath, Sleeps 8
Stockbridge, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
Prime Location And Charm
4 Bedrooms, 2.5 Baths, Sleeps 8
Stockbridge, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Stockbridge Cape Near Tanglewood
4 Bedrooms, 2 Bath, Sleeps 7
Stockbridge, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Taggart River House
5 Bedrooms, 5 Baths, Sleeps 10
Stockbridge, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Tanglewood Treasure!
3 Bedrooms, 2 Baths, Sleeps 10
Stockbridge, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Walk Into Town
3 Bedrooms, 2.5 Baths, Sleeps 6
Stockbridge, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Washington, MA
Beautiful Timber Frame Home
2 Bedrooms, 1 Bath, Sleeps 6
Washington, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
West Stockbridge, MA
Sweet Escape w/Indoor Pool
4 Bedrooms, 4 Bath, Sleeps 7
West Stockbridge, MA
Southern Berkshires
No Pets
Vacation Home Rental Rates & Information
Williamstown, MA
Charming Downtown Williamstown Cottage
3 Bedrooms, 2 Bath, Sleeps 7
Williamstown, MA
Northern Berkshires
No Pets
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
North Getaway Cottage
4 Bedrooms, 2 Bath, Sleeps 7
Williamstown, MA
Northern Berkshires
No Pets
Vacation Home Rental Rates & Information