Vacation Rentals In North Egremont MA, Vacation Rentals In The Berkshires, Vacation Home Rentals In The Berkshires, Vacation Homes For Rent In The Berkshires

View Over 85 Berkshire Vacation Rentals

 Stockbridge - Lenox - Lee - Becket - Otis ...And More! 

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Vacation Rentals In Lenox MA, Vacation Rentals In The Berkshires, Vacation Home Rentals In The Berkshires, Vacation Homes For Rent Tanglewood Berkshires

Charming Spacious

Home, Stunning Views

5 Bedrooms, 5 Baths, Sleeps 14

Just Steps To Tanglewood

Lenox, MA

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Vacation Rentals In Lee MA, Vacation Rentals In The Berkshires, Vacation Home Rentals In Lee MA, Vacation Homes For Rent Tanglewood Berkshires

Minutes To Tanglewood,

Jacobs Pillow & More!

 4 Bedrooms, 3 Baths, Sleeps 8

Spacious Historic Home

Pet Friendly

Lee, MA

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Lake Vacation Rentals In Lanesboro MA, Vacation Rentals In The Berkshires, Vacation Home Rentals In The Berkshires, Vacation Homes For Rent Berkshires

The Lake House Guest

Cottages Of The Berkshires

 Waterfront Boutique-Style Cottages

On Pristine Pontoosuc Lake

Lanesboro, MA

(413) 446-0017

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Vacation Rentals In Tyringham MA, Vacation Rentals In The Berkshires, Vacation Home Rentals In The Berkshires, Vacation Homes For Rent Tanglewood Berkshires

Charming And Spacious

Colonial Farmhouse

4 Bedrooms, 2 Baths, Sleeps 8

On The Santarella Estate

Tyringham, MA

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Vacation Rentals In Great Barrington MA, Vacation Rentals In The Berkshires, Vacation Home Rentals In The Berkshires, Vacation Homes For Rent Berkshires

Gartner House, A

Charming Lenox House

 4 Bedrooms, 1 Bath, Sleeps 7

 Short Ride To Tanglewood

Pet Friendly

Lenox, MA

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Vacation Rentals In Savoy MA, Vacation Rentals In The Berkshires, Vacation Home Rentals In The Berkshires, Vacation Homes For Rent Berkshires

Retreat In The Woods

With 2 Person Jacuzzi

 2 Bedrooms, 1 Bath, Sleeps 4

 Near State Forest & Hiking

Savoy, MA

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Vacation Rentals In West Stockbridge MA, Vacation Rentals In The Berkshires, Vacation Home Rentals In The Berkshires, Vacation Homes For Rent Berkshires

Berkshire Farmhouse

Vacation

5 Bedrooms, 2 Baths, Sleeps 12

 Gorgeous Screened-In Porch

Pet Friendly

West Stockbridge, MA

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Vacation Rentals In Stockbridge MA, Vacation Rentals In The Berkshires, Vacation Home Rentals In The Berkshires, Vacation Homes For Rent Berkshires

Cultural Playground

5 Min. To Tanglewood

 2 Bedrooms, 2 Baths, Sleeps 6

 Wonderful Views

Pet Friendly

Stockbridge, MA

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Vacation Rentals In Lee MA, Vacation Rentals In The Berkshires, Vacation Home Rentals In Lee MA, Vacation Homes For Rent Tanglewood Berkshires

Deluxe New 5 Bedroom, Available Thanksgiving, Christmas, Summer & Winter Months!!!

 5 Bedrooms, 5 Baths, Sleeps 10-12

Lee, MA

Please Call Owner: (954) 778-0808 or (954) 753-6699

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Vacation Rentals

Vacation Rentals

Becket, MA
Beautiful Colonial In Secluded Berkshires
6 Bedrooms, 3 Baths, Sleeps 11
Becket, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Berkshires On The Pond
2 Bedrooms, 1 Bath, Sleeps 2
Becket, MA
Central Berkshires
Vacation Home Rental Rates & Information


Charming Home Nestled In The Berkshires
3 Bedrooms, 4 Baths, Sleeps 6
Becket, MA
Central Berkshires
Vacation Home Rental Rates & Information


Escape To The Berkshires
4 Bedrooms, 3 Baths, Sleeps 8
Becket, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Serene Lakfront Cottage
2 Bedrooms, 2 Baths, Sleeps 4
Becket, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Spacious Wooded Home
4 Bedrooms, 5 Baths, Sleeps 12
Becket, MA
Central Berkshires
Vacation Home Rental Rates & Information


Stunning Becket Woods Contemporary
4 Bedrooms, 3 Baths, Sleeps 10
Becket, MA
Central Berkshires
Vacation Home Rental Rates & Information


Quiet Comfortable Cabin
5 Minute Walk To Lake
2 Bedrooms, 1 Bath, Sleeps 4
Becket, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
                        

Cheshire, MA
Charming Berkshires Lakefront House
2 Bedrooms, 1 Bath, Sleeps 5
Cheshire, MA
Northern Berkshires
Vacation Home Rental Rates & Information


Great Barrington, MA
1940's Cabin With
Fantastic Mountain View
2 Bedrooms, 1 Bath, Sleeps 5
Great Barrington, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Bekshire Estate: Exquisitely
Furnished 7,000 Sq. Ft.
6 Bedrooms, 6 Baths, Sleeps 12
Great Barrington, MA
Southern Berkshires
Vacation Home Rental Rates & Information


Berkshires Romantic Cottage
With Spectacular View
1 Bedroom, 1 Bath, Sleeps 3
Great Barrington, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Charming Get-A-Way In Great Barrington
3 Bedrooms, 1 Bath, Sleeps 6
Great Barrington, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Country Elegance In The Berskhires
4 Bedrooms, 6 Baths, Sleeps 12
Great Barrington, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Shaker Hill
5 Bedrooms, 4 Baths, Sleeps 10
Great Barrington, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
                        

Hancock, MA
2200 Sq. Ft. Country House On 16 Acres
4 Bedrooms, 2 Baths, Sleeps 9
Hancock, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Christmas In The Berkshires
1 Bedroom, 2 Baths, Sleeps 4
Hancock, MA
Northern Berkshires
Vacation Home Rental Rates & Information


Golden Triangle In The Berkshires
2 Bedrooms, 2 Baths, Sleeps 4
Hancock, MA
Northern Berkshires
Vacation Home Rental Rates & Information


Luxury Resort In Hancock
2 Bedrooms, 2 Baths, Sleeps 8
Hancock, MA
Northern Berkshires
Vacation Home Rental Rates & Information


Panoramic View 1,000 Sq. Ft.
Guest Quarters
1 Bedroom, 1 Bath, Sleeps 6
Hancock, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Private Home on 27 Acres Near Jiminy Peak
3 Bedrooms, 2 Baths, Sleeps 8
Hancock, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Ski Jiminy Peak Condo
3 Bedrooms, 2 Baths, Sleeps 6
Hancock, MA
Northern Berkshires
Vacation Home Rental Rates & Information


Wyndham Bentley Brook At Jiminy Peak
2 Bedrooms, 2 Baths, Sleeps 6
Hancock, MA
Northern Berkshires
Vacation Home Rental Rates & Information
                        

Hinsdale, MA
Beautiful Lindal Cedar Home With Great

Lake Views
4 Bedrooms, 3 Baths, Sleeps 8
Hinsdale, MA
Central Berkshires
Vacation Home Rental Rates & Information


New Timberframe House Rental In
The Berkshires
3 Bedrooms, 2 Baths, Sleeps 7
Hinsdale, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
                        

Lanesboro, MA
Stone School Cottage
2 Bedrooms, 1 Bath, Sleeps 4
Lanesboro, MA
Northern Berkshires
Vacation Home Rental Rates & Information

 

The Lake House Guest Cottages

Of The Berkshires
Waterfront Boutique-Style Cottages
On Pristine Pontoosuc Lake
Lanesboro, MA
Northern Berkshires
Vacation Home Rental Rates & Information

 

Lee, MA

Deluxe New 5 Bedroom, Available Thanksgiving, Christmas, Summer and Winter Months!
5 Bedrooms, 5 Baths, Sleeps 10-12
Lee, MA
Call Owner (954) 778-0808 or (954) 753-6699
Southern Berkshires
Vacation Home Rental Rates & Information

Jacob's Tanglewood
5 Bedrooms, 5 Baths, Sleeps 10
Lee, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Rivers End Room In
The Barn At Chestnut Lodge
1 Bedroom, 2 Baths, Sleeps 5
Lee, MA    01238    
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Lenox, MA
A Cute 2 Bedroom House Near
Dowtown Lenox
2 Bedrooms, 1 Bath, Sleeps 4
Lenox, MA
Central Berkshires
Vacation Home Rental Rates & Information


Charming Spacious Home, Stunning Views
5 Bedrooms, 5 Baths, Sleeps 14
Lenox, MA
Central Berkshires
Vacation Home Rental Rates & Information


Gartner House, A Charming Lenox House
4 Bedrooms, 1 Bath, Sleeps 7
Lenox, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Interior Designers Cozy Hideaway
1 Bedroom, 1 Bath, Sleeps 3
Lenox, MA
Central Berkshires
Vacation Home Rental Rates & Information


Walk To Tanglewood Or Shakespeare & Co.
2 Bedrooms, 1 Bath, Sleeps 5
Lenox, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


New Marlborough, MA
Country Victorian Serenity In The Berkshires
4 Bedrooms, 2 Baths, Sleeps 6
New Marlborough, MA
Southern Berkshires
Vacation Home Rental Rates & Information


North Egremont, MA
RiverSong Suite In The Berkshires
1 Bedroom, 1 Bath, Sleeps 2
North Egremont, MA
Southern Berkshires
Vacation Home Rental Rates & Information
                        

Monterey, MA
Beautiful Berkshire Post And Beam House
5 Bedrooms, 2 Baths, Sleeps 12
Monterey, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Beautiful Lakefront Berkshire Rental
5 Bedrooms, 2 Baths, Sleeps 6
Monterey, MA
Southern Berkshires
Vacation Home Rental Rates & Information


Pittsfield, MA
Berkshire Getaway…
Peace & Tranqulity
3 Bedrooms, 2 Baths, Sleeps 8
Pittsfield, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Luxury Ski In/Ski Out
Jiminy Peak Mtn. Resort
3 Bedrooms, 2 Baths, Sleeps 8
Pittsfield, MA
Central Berkshires
Vacation Home Rental Rates & Information


Richmond, MA
Lakeview Home with Swingset & Firepit
3 Bedrooms, 1 Baths, Sleeps 6
Richmond, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


New Pristine Berkshire Vacation Rental

With Pool
3 Bedrooms, 3 Baths, Sleeps 6
Richmond, MA
Central Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Sandisfield, MA
Lake Community - Berkshires
3 Bedrooms, 3 Baths, Sleeps 6
Sandisfield, MA
Southern Berkshires
Vacation Home Rental Rates & Information


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

South Lee, MA
Historic South Lee Schoolhouse
Near Stockbridge
4 Bedrooms, 3 Baths, Sleeps 8
South Lee, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

Stockbridge, MA
Cultural Playground,
5 Minutes To Tanglewood
2 Bedrooms, 2 Baths, Sleeps 6
Stockbridge, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Fall/Winter - Spectacular
Setting - Family - Ski
3 Bedrooms, 3 Baths, Sleeps 8
Stockbridge, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Family - Friendly Cottage Near Lake, Tanglewood
2 Bedrooms, 2 Baths, Sleeps 7
Stockbridge, MA
Southern Berkshires
Vacation Home Rental Rates & Information


Solid Rock Farm In Southern Berkshires
2 Bedrooms, 2 Baths, Sleeps 8
Stockbridge, MA
Vacation Home Rental Rates & Information


Stockbridge Bowl House
2 Bedrooms, 2 Baths, Sleeps 8
Stockbridge, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information
                        

Tyringham, MA
Charming & Spacious Colonial Farmhouse
4 Bedrooms, 2 Baths, Sleeps 8
Tyringham, MA
Southern Berkshires
Vacation Home Rental Rates & Information
                        

West Stockbridge, MA
Berkshire Cottage Near Tanglewood
1 Bedroom, 1 Bath, Sleeps 2
West Stockbridge, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Berkshire Farmhouse Vacation
5 Bedrooms, 2 Baths, Sleeps 12
West Stockbridge, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Comfortable Farmhouse In The Berkshires
5 Bedrooms, 2 Baths, Sleeps 12
West Stockbridge, MA
Southern Berkshires
Vacation Home Rental Rates & Information


Cozy And Modern Home -
Minutes From Tanglewood
2 Bedrooms, 1 Bath, Sleeps 6
West Stockbridge, MA
Southern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information


Williamstown, MA
House On Main Street
4 Bedrooms, 3 Baths, Sleeps 16
Williamstown, MA
Northern Berkshires
Pet Friendly
Vacation Home Rental Rates & Information

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.