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300+ stays

Stays in Lanesborough

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SUPERHOST
Entire cottage in Hinsdale
Lakeside 3 bd Berkshires Getaway Relax with Us
8 guests3 bedrooms3 beds1 bathroom
WifiKitchenHeating
Rating 4.64 out of 5;30 reviews
Entire cottage in Lanesborough
Berkshires Waterfront Lakehouse
6 guests3 bedrooms4 beds1.5 bathrooms
WifiKitchenHeating
Rating 4.87 out of 5;112 reviews
SUPERHOST
Entire cottage in Lanesborough
The Sail Loft
4 guests1 bedroom2 beds1.5 bathrooms
WifiKitchenHeating
Rating 4.90 out of 5;41 reviews
Entire cottage in Lanesborough
Lake House w/ Deck & Views, Mins to Jiminy Peak!
10 guests3 bedrooms8 beds2 bathrooms
WifiKitchenHeating
Rating 4.90 out of 5;10 reviews
Entire apartment in Williamstown
Vacation Village in the Berkshires Resort Suite A
4 guests1 bedroom2 beds1 bathroom
WifiKitchenHeatingIndoor fireplace
SUPERHOST
Entire cabin in Stockbridge
NEW Stockbridge Cabin - A quick stroll to the lake
6 guests3 bedrooms5 beds1.5 bathrooms
WifiKitchenHeatingIndoor fireplace
Rating 4.89 out of 5;28 reviews
SUPERHOST
Entire flat in Pittsfield
Sharon's Place 5 Pet, and 420 friendly!!!!!!
2 guests1 bedroom2 beds1 bathroom
WifiKitchenHeating
Rating 4.79 out of 5;92 reviews
Entire cabin in Lanesborough
Luxury cabins
4 guestsStudio3 beds1 bathroom
WifiKitchenHeating
Rating 4.86 out of 5;21 reviews
SUPERHOST
Entire house in Dalton
Brooksong, the perfect Berkshires getaway
10 guests5 bedrooms7 beds2.5 bathrooms
WifiKitchenHeatingIndoor fireplace
Rating 4.96 out of 5;85 reviews
Entire house in Lenox
Mid-Century Modern Chic in Lenox
4 guests2 bedrooms2 beds2 bathrooms
WifiKitchenHeatingIndoor fireplace
Rating 4.52 out of 5;79 reviews
Entire house in Cheshire
BEAUTIFUL LOG HOME
7 guests3 bedrooms4 beds2.5 bathrooms
WifiKitchenHeating
Rating 4.89 out of 5;98 reviews
Entire house in Pittsfield
Honeysuckle Rose Cottage
4 guests2 bedrooms2 beds1 bathroom
WifiKitchenHeating
Rating 4.80 out of 5;248 reviews
SUPERHOST
Entire apartment in Hancock
Cozy Condo @ Jiminy Peak
5 guests2 bedrooms2 beds1.5 bathrooms
WifiKitchenHeatingIndoor fireplace
Rating 4.69 out of 5;39 reviews
Entire house in Hancock
Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!
6 guests3 bedrooms3 beds2 bathrooms
WifiKitchenHeatingIndoor fireplace
Rating 4.89 out of 5;19 reviews
SUPERHOST
Entire apartment in Hancock
Furnished Condo at Jiminy Peak (For Sale $288,000)
6 guests2 bedrooms3 beds2 bathrooms
WifiKitchenHeatingIndoor fireplace
Rating 4.96 out of 5;26 reviews
SUPERHOST
Entire house in Lanesborough
Elmwood Farmhouse
11 guests4 bedrooms6 beds2.5 bathrooms
WifiKitchenHeatingIndoor fireplace
Rating 4.84 out of 5;44 reviews
Entire apartment in Williamstown
Vacation Village in the Berkshires Resort Suite B
4 guests1 bedroom2 beds1 bathroom
WifiKitchenHeatingIndoor fireplace
Entire house in Pittsfield
Spacious and quiet central Berkshire home!
6 guests4 bedrooms3 beds2 bathrooms
WifiKitchenHeating
SUPERHOST
Entire flat in Pittsfield
Berkshires Charm, Downtown Convenience
4 guests2 bedrooms2 beds1 bathroom
WifiKitchenHeating
Rating 4.81 out of 5;16 reviews
SUPERHOST
Entire cottage in Lanesborough
Stone School Cottage
5 guests2 bedrooms4 beds1 bathroom
WifiKitchenHeating
Rating 4.91 out of 5;141 reviews
120 of 300+ places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.