300+ stays

Stays in Stockbridge

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SUPERHOST
Entire cottage in West Stockbridge
Cozy Stockbridge Cottage
5 guests2 bedrooms3 beds1 bath
WifiKitchenHeatingFree parking
$98 per night
SUPERHOST
Private room in Lee
Comfortable living in 1870's house!
2 guests1 bedroom1 bed1.5 shared baths
WifiHeatingFree parking
$43 per night
Entire apartment in Great Barrington
The Treehouse
3 guests2 bedrooms2 beds1 bath
WifiKitchenHeatingFree parking
$109 per night
SUPERHOST
Private room in Stockbridge
Villa Favorita
2 guests1 bedroom1 bed1 private bath
WifiHeatingFree parking
$80 per night
Entire house in Lenox
Mid-Century Modern Chic in Lenox
4 guests2 bedrooms2 beds2 baths
WifiKitchenHeatingFree parking
$175 per night
Entire apartment in Great Barrington
The Nest
3 guests1 bedroom1 bed1 bath
WifiKitchenHeatingFree parking
$100 per night
Entire cottage in Great Barrington
Artist Cottage at the Foot of Monument Mountain
2 guests1 bedroom1 bed2 baths
WifiKitchenHeatingFree parking
$204 per night
Entire house in Pittsfield
Dancing Horse Lodge
6 guests3 bedrooms3 beds1 bath
WifiKitchenHeatingFree parking
$85 per night
SUPERHOST
Entire cottage in New Lebanon
The Writer's Cottage
3 guests1 bedroom2 beds1 bath
WifiKitchenHeatingFree parking
$95 per night
SUPERHOST
Entire house in Lenox
Berkshire, MA Getaway!
6 guests3 bedrooms3 beds1 bath
WifiKitchenHeatingFree parking
$155 per night
Entire apartment in Albany Area
Cozy Suite with huge bar and stone fireplace!
4 guestsStudio0 beds1 bath
WifiKitchenHeatingFree parking
$55 per night
Entire apartment in Lenox
Station House 1E Private Room & Bath
2 guests1 bedroom1 bed1 bath
WifiHeatingFree parking
$56 per night
SUPERHOST
Entire guesthouse in Canaan
Airy cottage with meadow views in The Berkshires
4 guests1 bedroom3 beds1 bath
WifiKitchenHeatingFree parking
$145 per night
Room in boutique hotel in Lenox
Terrace House King
2 guests1 bedroom1 bed1 bath
WifiHeatingFree parking
$138 per night
SUPERHOST
Entire house in Lee
Cozy Berkshires Cottage
4 guests1 bedroom1 bed1 bath
WifiKitchenHeatingFree parking
$118 per night
SUPERHOST
Entire apartment in Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
4 guests2 bedrooms2 beds1.5 baths
WifiKitchenHeatingFree parking
$75 per night
SUPERHOST
Private room in Lee
Beautiful Downtown Lee setting
2 guests1 bedroom1 bed1.5 baths
WifiHeatingFree parking
$48 per night
Entire house in Canaan
Country Cottage
5 guests3 bedrooms3 beds2 baths
WifiKitchenHeatingFree parking
$125 per night
Entire house in Pittsfield
Honeysuckle Rose Cottage
4 guests2 bedrooms2 beds1 bath
WifiKitchenHeatingFree parking
$120 per night
Hotel room in Lee
1 King Bed
2 guests1 bedroom1 bed1 private bath
WifiHeatingFree parking
$55 per night
1 – 20 of 300+ places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.