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!
North Adams, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Beautiful Lakeside Home In The North
Adams/Williamstown Area.
Sleeps: 8
Bedrooms: 3
Bathrooms: 1.5
No Pets
North Adams, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Pleasant On Pleasant, Modern
Conveniences And Fresh Decor.
Sleeps: 7
Bedrooms: 2
Bathrooms: 2
Pets Welcome
North Adams, MA
Northern Berkshire Area
Berkshire Vacation Rentals
Large Duplex Near MASS MoCA
MCLA, Recent Complete Renovation.
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
No Pets
Otis, MA
Southern Berkshire Area
Berkshire Vacation Rentals
4BR Berkshire Lakefront/Ski House,
Fully Fitted Kitchen. Hi Speed WiFi.
Sleeps: 10
Bedrooms: 4
Bathrooms: 3
No Pets
Otis, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Modern Secluded Home In Wooded
Setting, 2,500 Sq. Ft..
Sleeps: 8
Bedrooms: 3
Bathrooms: 2.5
No Pets
Otis, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Secluded Cabin On Acres Of Woods Lake Access, Has Everything You Need.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Otis, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Spacious Waterfront Berkshire Home,
Family Private Get-Away.
Sleeps: 8
Bedrooms: 4
Bathrooms: 3
No Pets
Otis, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Charming 3 Bedroom Cedar Shingle
Lakefront Cottage.
Sleeps: 7
Bedrooms: 3
Bathrooms: 1
No Pets
Otis, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Luxury Home In Scenic Wooded
Area With Private Lake, Sleeps 16.
Sleeps: 16
Bedrooms: 4
Bathrooms: 2.5
Pets Welcome
Otis, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Beautiful 3 BR Lakeside Log Home
Close To All Berkshires Attractions.
Sleeps: 8
Bedrooms: 3
Bathrooms: 2
No Pets
Otis, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Lovely Loft By Brook And Lake In
Private Berkshire Community.
Sleeps: 6
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Otis, MA
Southern Berkshire Area
Berkshire Vacation Rentals
East Otis Reservoir Cabin With Porch,
Walk to Lake!
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
Pets Welcome
Otis, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Modern Berkshires Cottage Gas Stove, Large Deck & W/D + 7 Mins To Otis Ridge.
Sleeps: 10
Bedrooms: 2
Bathrooms: 2
No Pets
Otis, MA
Southern Berkshire Area
Berkshire Vacation Rentals
NEW! East Otis Romantic
Cottage w/Deck & BBQ!
Sleeps: 2
Bedrooms: Studio
Bathrooms: 1
No Pets
Otis, MA
Southern Berkshire Area
Berkshire Vacation Rentals
The Meadows House @ Otis Ridge w/7-Person Hot Tub, 4-Season Ski House.
Sleeps: 7
Bedrooms: 3
Bathrooms: 2.5
No Pets
Peru, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Swiss Chalet Style Timber Frame
Home With All Modern Conveniences.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Berkshire Pontoosuc Lake Beauty,
Brand New Construction On Lake.
Sleeps: 14
Bedrooms: 5
Bathrooms: 3.5
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Tranquil Lake House Getaway
On Onota Lake, 5BR, 2BA.
Sleeps: 11
Bedrooms: 5
Bathrooms: 2
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Dancing Horse Lodge, Located On Horse Farm, Next To Bosquet Ski Area.
Sleeps: 6
Bedrooms: 3
Bathrooms: 1
Pets Welcome
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Newly Renovated 4 Bedroom
Lakefront House In The Berkshires.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2.5
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Beautiful Waterfront Home With
Deep Water Dock On Onota Lake.
Sleeps: 12
Bedrooms: 3
Bathrooms: 2
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Lake Front Home In Heart Of The
Berkshires Near Jiminy Peak.
Sleeps: 10
Bedrooms: 4
Bathrooms: 4
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Beautiful Log Cabin In The Woods, On
Pontoosuc Lake, Yet Near Everything.
Sleeps: 5
Bedrooms: 2
Bathrooms: 1.5
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
6 Bedroom, Lakeside Home With
Pool, Completely Renovated.
Sleeps: 16
Bedrooms: 6
Bathrooms: 4.5
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Historic Red Schoolhouse Featured
In 2015 Home & Garden TV Special.
Sleeps: 4
Bedrooms: 1
Bathrooms: 1
Pets Welcome
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Apartment Newly Remodeled Super Location, Large Covered Porch.
Sleeps: 4
Bedrooms: 2
Bathrooms: 1
No Pets
Pittsfield, MA
Central Berkshire Area
Berkshire Vacation Rentals
Spacious Berkshire Summer Rental,
Private Dock On Lake 3 BR/2BA.
Sleeps: 7
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Richmond, MA
Central Berkshire Area
Berkshire Vacation Rentals
Morning Face – Berkshire Estate
With Views And Privacy.
Sleeps: 10
Bedrooms: 4
Bathrooms: 4.5
No Pets
Richmond, MA
Central Berkshire Area
Berkshire Vacation Rentals
Safe & Cozy Berkshires Getaway, Welcome Break In Routine You Need!
Sleeps: 6
Bedrooms: 3
Bathrooms: 2
No Pets
Richmond, MA
Central Berkshire Area
Berkshire Vacation Rentals
Recently Renovated 4BR Lakefront House In The Berkshires, Three Decks.
Sleeps: 8
Bedrooms: 4
Bathrooms: 2.5
No Pets
Sandisfield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Cabin w/3 Acres, Tennis + Basketball
Courts By 4 Ski Mountains.
Sleeps: 12
Bedrooms: 4
Bathrooms: 3
Pets Welcome
Sandisfield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Sweet Dreams Retreat, Newly
Renovated Luxury Guest House.
Sleeps: 3
Bedrooms: 1
Bathrooms: 1
Pets Welcome
Sandisfield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Waterfront Oasis In The Heart Of The Berkshires, Steps From Private Pond, Patio.
Sleeps: 6
Bedrooms: 3
Bathrooms: 3
No Pets
Sandisfield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Iconic Cabin In The Berkshires, Stone Fireplace, Yoga & Indoor Endless Swimming Pool.
Sleeps: 12
Bedrooms: 6
Bathrooms: 3.5
Pets Welcome
Sheffield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Family Friendly In Sheffield, Private Yet Close To Everything! Your Perfect Country Escape.
Sleeps: 10
Bedrooms: 4
Bathrooms: 3.5
Pets Welcome
Sheffield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Serene Berkshire Artist’s House
Situated On 5 Quiet Acres.
Sleeps: 6
Bedrooms: 3
Bathrooms: 2.5
No Pets
Sheffield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Elterwater–Sought After And Rare
Private Idyllic Berkshire Lakefront.
Sleeps: 4
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Sheffield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
Private Peninsula Surrounded By
Water, Minutes From Hiking & More!
Sleeps: 9
Bedrooms: 3
Bathrooms: 2
Pets Welcome
Sheffield, MA
Southern Berkshire Area
Berkshire Vacation Rentals
The Little House In The Woods
Fresh, Cozy & Serene
Sleeps: 6
Bedrooms: 2
Bathrooms: 2
Pets Welcome