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Number of reviews
141 Houses
Price per night from
$296
Comfortable Farmhouse in the Berkshires
West Stockbridge farmhouse
5 bedrooms / 3 bathrooms / sleeps 12
Responds fast! avg. 1 hour 34 minutes
Price per night from
$385
Cozy & Modern Home -mins from Tanglewood & Kripalu
West Stockbridge apartment
2 bedrooms / 1 bathroom / sleeps 6
Price per night from
$119
To Ski or Not to Ski? Great conditions Great fireplace.Your Choice.
West Stockbridge house
3 bedrooms / 3 bathrooms / sleeps 8
“A memorable weekend getaway includes the most perfect house..” My husband and I had the pleasure to rent out this house last summer with another married couple and their son. Although our daughter and their son truly enjoyed Tanglewood and our visits into Town (which are both extremely close), I can't help but think that my favorite part of our vacation was the house we were staying in! The space felt both warm and welcoming and fit our group size perfectly. We also had access to a private quarry that the owners have rights to- bonus! I am quite disappointed that our summer dates are already booked.. but have already started to plan for this Fall.
Responds fast! avg. 2 hours 17 minutes
Price per night from
$415
“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the living room and paneled walls in the dining room. We were there on a rainy, cold weekend, so did not have an opportunity to enjoy the grounds or porch, but imagine it would be lovely in the warmer weather. Elaine (and her shop) were on the same grounds and she was available for questions about the area. Overall a very relaxing & convenient experience.
Price per night from
$305
Price per night from
$249
Great rentals within 20 miles that match your search
Price per night from
$534
Price per night from
$593
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
$702
Responds fast! avg. 1 hour 1 minutes
Price per night from
$466
Responds fast! avg. 3 hours 42 minutes
Price per night from
$153
Berkshire Blueberry Lodge LLC - Near Jiminy Peak
Stephentown lodge
4 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$444
The perfect Southern Berkshire winter vacation esc
Sheffield house
4 bedrooms / 2 bathrooms / sleeps 10
Price per night from
$592
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
$355
Price per night from
$201
Big Beautiful 7 bedroom 3 bath hot tub pool table
Pittsfield house
7 bedrooms / 3 bathrooms / sleeps 18
Price per night from
$355
Picturesque 19th century home on 3 private acres
New Marlborough house
4 bedrooms / 2 bathrooms / sleeps 7
Price per night from
$178
Price per night from
$473
Price per night from
$2,956
Price per night from
$710
7 night Christmas week Wyndham Bentley Brook 2 bdr condo Slopeside
Hancock condo
2 bedrooms / 2 bathrooms / sleeps 8
Price per night from
$237
Responds fast! avg. 3 hours 4 minutes
Price per night from
$326
Turning Point - Family Retreat & Group Getaway
Great Barrington house
7 bedrooms / 8 bathrooms / sleeps 15
Price per night from
$948
Price per night from
$272
Jiminy Peak Ski Resort-Country Village's Best Unit
Hancock apartment
2 bedrooms / 2 bathrooms / sleeps 6
Price per night from
$297
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
$267
Price per night from
$506
Cozy and clean in Gt Barrington- available for October
Great Barrington house
2 bedrooms / 2 bathrooms / sleeps 4
Price per night from
$178
Charming Private Guest Suite in Historic Village in the Berkshires
New Marlborough studio
Studio / 1 bathroom / sleeps 2
Price per night from
$113
“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
$237
Price per night from
$212
Newly Renovated Colonial on the River! Sleeps 5-6
Stockbridge house
3 bedrooms / 2 bathrooms / sleeps 5
Price per night from
$338
Walk To Tanglewood, Stocbridge Bowl, Wheatleigh, HTD Pool, Hot Tub, Luxury Home
Lenox house
5 bedrooms / 5 bathrooms / sleeps 15
Price per night from
$1,179
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