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. Below, you will 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!
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Grand Estate in Historic Stockbridge
9,000 Sq. Ft., Sleeps 12.
Sleeps: 12
Bedrooms: 6
Bathrooms: 7
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Spacious & Modern Berkshires Getaway, Firepit, 6 Person Hot Tub.
Sleeps: 8
Bedrooms: Studio
Bathrooms: 1
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
1 Block From Main St. Stockbridge, No Children Please, Open, Airy Feel w/A Cathedral Ceiling.
Sleeps: 4
Bedrooms: 2
Bathrooms: 2
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Stockbridge Home, Come Experience The Berkshires! Screened In Porch.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Newly Refurbished Artist’s Cottage
On The Lake Mahkeenac.
Sleeps: 4
Bedrooms: 3
Bathrooms: 1
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Sophisticated & Comfortable Retreat
A+ Location, Modern Amenities.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
4 BR, 3.5 BA, Renovated Perfect
Location, Summer Arts, Winter Skiing.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Vacation In A 5 Bedroom, 2 Bath,
Berkshire Farmhouse.
Sleeps: 15
Bedrooms: 5
Bathrooms: 2
Pets Welcome
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Completely Renovated Historic Home
In The Heart Of The Berkshires.
Sleeps: 6
Bedrooms: 2
Bathrooms: 2.5
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
NEW! Cozy Berkshires Cabin,
Walk To Beach & Lake!
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Beautiful Farm House Near Family
Ski Mountains & Other Fun Activities.
Sleeps: 8
Bedrooms: 4
Bathrooms: 4
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Charming Cottage In Norman Rockwell’s Stockbridge, 2 Decks! Hammock, Pets Welcome.
Sleeps: 6
Bedrooms: 4
Bathrooms: 1
Pets Welcome
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Clean & Modern Space w/A Mix Of Original Warmth & Charming Renovation.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Renovated Colonial on the River!
Fantastic Views.
Sleeps: 5
Bedrooms: 3
Bathrooms: 2
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Stockbridge Classic 1880 Farmhouse
Newly Renovated.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Rabbit Run – In The Heart Of
Stockbridge, walk To Red Lion Inn.
Sleeps: 7
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Elegant & Private Light-Filled 1 Level, Full Season Rental, Lovely, Quiet & Spacious.
Sleeps: 5
Bedrooms: 3
Bathrooms: 3
Pets Welcome
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Location!!! Berkshire Glamour (and
comfort) Meets Town And Country.
Sleeps: 10
Bedrooms: 3
Bathrooms: 3
Pets Welcome
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Stockbridge Bowl Lake Community,
Exc. Location, Close To Everything!
Sleeps: 7
Bedrooms: 4
Bathrooms: 2
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Family Getaway In Stockbridge Woods
Mins. To Tanglewood, Lenox & GB.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Cozy Modern Rental (Minutes From
Lenox, Kripalu & Tanglewood).
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Stockbridge Cape Near Tanglewood & Kripalu – Heart Of The Berkshires!
Sleeps: 7
Bedrooms: 4
Bathrooms: 2
Pets Considered
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Stockbridge! 1/2 Mile From Red Lion
Inn. Gt. Barrington, Lenox, Lee Close.
Sleeps: 12
Bedrooms: 4
Bathrooms: 3.5
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Modern, Secluded Cottage In The
Heart Of The Berkshires!
Sleeps: 8
Bedrooms: 3
Bathrooms: 2.5
Pets Welcome
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Home w/Pool On 10 Acres, Expansive 2-Tier Deck, Pool House, Manicured Grounds.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Tranquil 3 Bedroom Stockbridge
House With Private Deck.
Sleeps: 6
Bedrooms: 3
Bathrooms: 1.5
No Pets
Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Cabin Fever In Stockbridge,
2 Bedroom Cabin Fully Remodeled.
Sleeps: 6
Bedrooms: 2
Bathrooms: 1
No Pets
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Charming Unique Cottage, Stunning Mountains w/Private Views! Hiking, Mountain Biking Trails.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
Pets Welcome
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
4 Bedroom Home, Beautiful Gardens,
On Pond, Walking Distance To Town.
Sleeps: 10
Bedrooms: 4
Bathrooms: 2
No Pets
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Secluded Mountaintop Retreat In The Heart Of The Berkshires, Front & Back Patios.
Sleeps: 6
Bedrooms: 3
Bathrooms: 3.5
No Pets
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Vacation In A Berkshire Farmhouse,
5 Bedrooms, 2 Baths, Sleeps 11-15.
Sleeps: 15
Bedrooms: 5
Bathrooms: 2
Pets Welcome
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Loft Style Cabin In West Stockbridge, Book Now! Two Patio Areas.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2
Pets Welcome
West Stockbridge, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Gorgeous Home, Nature Lover’s
Delight In The Heart Of The Berkshires.
Sleeps: 8
Bedrooms: 3
Bathrooms: 3.5
No Pets
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
NEW! Peaceful Family Home w/Fire Pit & Large Yard w/Adirondack Chairs.
Sleeps: 6
Bedrooms: 3
Bathrooms: 3
No Pets
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Cozy And Quaint Country Cottage,
Walk To Downtown Williamstown.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
11 Acre Mid-Century Estate,
Newly Renovated.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3.5
No Pets
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Charming Downtown Williamstown
Cottage – 5 Minute Walk to Campus.
Sleeps: 7
Bedrooms: 3
Bathrooms: 2
No Pets
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Cozy And Quaint Country Cottage,
Walk To Downtown Williamstown.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Fun Filmmaker’s Bungalow w/Pool & Pro Screening Room, Well-Located.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1
No Pets
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Vacation Rental Home In The Berkshires! Patio, Fire Pit, Mountain Views.
Sleeps: 2
Bedrooms: 1
Bathrooms: 1
No Pets
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Huge Luxe Williamstown Updated
Victorian, Walk to Spring Street.
Sleeps: 10
Bedrooms: 5
Bathrooms: 5.5
Pets Welcome
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Cozy Renovated Williamstown Cabin,
Steps From Hiking Trails.
Sleeps: 5
Bedrooms: 2
Bathrooms: 2
No Pets
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Charming Downtown Williamstown
Cottage, 5 Minute Walk To Campus.
Sleeps: 7
Bedrooms: 3
Bathrooms: 2
No Pets
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Large, Family-Friendly Farmhouse
Located In The Beautiful Berkshires.
Sleeps: 13
Bedrooms: 6
Bathrooms: 2.5
No Pets
Williamstown, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Vacation Getaway Or Remote
Work/School Location
Sleeps: 7
Bedrooms: 4
Bathrooms: 2
No Pets