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136 Houses
Price per night from
$249
3BD Newly Rennovated Contempoary Near Stockbridge
Stockbridge house
3 bedrooms / 3 bathrooms / sleeps 6
Price per night from
$349
One of the Finest Homes and Best location in the Berkshires
Stockbridge house
4 bedrooms / 3 bathrooms / sleeps 10
Price per night from
$814
Responds fast! avg. 5 minutes
Price per night from
$266
Price per night from
$872
Family-friendly Cottage Near Lake, Tanglewood
Stockbridge cottage
3 bedrooms / 2 bathrooms / sleeps 7
Price per night from
$327
Responds fast! avg. 6 minutes
Price per night from
$249
"Too Good" With 11 Private Acres. Contact us for Monthly Specials!
Stockbridge house
4 bedrooms / 4 bathrooms / sleeps 12
Price per night from
$629
Newly Renovated Colonial on the River! Sleeps 5-6
Stockbridge house
3 bedrooms / 2 bathrooms / sleeps 5
Price per night from
$332
Great rentals within 20 miles that match your search
Price per night from
$524
Price per night from
$582
Luxury Fox Hollow Estate Home on Laurel Lake, Hot Tub, Dock with Kayak, Canoe++
Lenox house
5 bedrooms / 3 bathrooms / sleeps 14
Price per night from
$689
Responds fast! avg. 1 hour 1 minutes
Price per night from
$458
Responds fast! avg. 3 hours 42 minutes
Price per night from
$150
Berkshire Blueberry Lodge LLC - Near Jiminy Peak
Stephentown lodge
4 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$436
The perfect Southern Berkshire winter vacation esc
Sheffield house
4 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$581
Berkshires Spacious Comfortable Charming Farmhouse
Lee apartment
3 bedrooms / 2 bathrooms / sleeps 8
“lovely stay” The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.
Price per night from
$348
Price per night from
$198
Big Beautiful 7 bedroom 3 bath hot tub pool table
Pittsfield house
7 bedrooms / 3 bathrooms / sleeps 18
Price per night from
$348
Picturesque 19th century home on 3 private acres
New Marlborough house
4 bedrooms / 2 bathrooms / sleeps 7
Price per night from
$174
Price per night from
$465
Price per night from
$244
Price per night from
$523
Price per night from
$697
7 night Christmas week Wyndham Bentley Brook 2 bdr condo Slopeside
Hancock condo
2 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$232
Responds fast! avg. 3 hours 4 minutes
Price per night from
$320
Turning Point - Family Retreat & Group Getaway
Great Barrington house
7 bedrooms / 8 bathrooms / sleeps 15
Price per night from
$930
Price per night from
$267
Jiminy Peak Ski Resort-Country Village's Best Unit
Hancock apartment
2 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$291
2200sf Country House on 16 Acres-2 Miles to Jiminy
Hancock house
4 bedrooms / 2 bathrooms / sleeps 9
“Great house Jiminy Peak” We (family of 4) stayed a weekend in January 2010 with friends (family of 5). It is a great house, perfect location and the owner is really great to deal with. Highly recommended for everyone with kids. easy drive to the slopes. well maintained and very clean.
Price per night from
$262
Price per night from
$497
Cozy and clean in Gt Barrington- available for October
Great Barrington house
2 bedrooms / 2 bathrooms / sleeps 4
Price per night from
$175
Charming Private Guest Suite in Historic Village in the Berkshires
New Marlborough studio
Studio / 1 bathroom / sleeps 2
Price per night from
$111
“Great Location In Lenox” My family, friends, & I had a wonderful 2 weeks at Gartner House. It is within easy walking distance of nice shops, terrific restaurants, & a friendly library. Not far are Chesterwood, Tanglewood, Jacob's Pillow, Mass MoCa, Norman Rockwell, & a great, newly renovated Beshire Museum in Pittsfield.
Price per night from
$233
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