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72 properties are available in and around this destination

HancockShow on map
20 miles from Tanglewood in Hancock, Cozy Cabin on Mountain Resort offers accommodations with access to a fitness center. This property offers a private pool and free private parking.
HancockShow on map
Spacious 3BR 3BA Sleeps 8 Ski On Off Jiminy Mountain Resort is located in Hancock, just 21 miles from Cranwell Spa & Golf Club and 21 miles from Tanglewood Musical Center.
HancockShow on map
Family-Friendly Hancock Home Walk to Slopes! is located in Hancock, just 21 miles from Cranwell Spa & Golf Club and 21 miles from Tanglewood Musical Center.
HancockShow on map
Jiminy Peak Mountainside Getaway in the Berkshires offers accommodations in Hancock, 21 miles from Tanglewood and 21 miles from Cranwell Spa & Golf Club.
HancockShow on map
20 miles from Tanglewood in Hancock, Mountainside Condo @ Jiminy Peak in the Berkshires offers accommodations with access to a hot tub.
HancockShow on map
23 miles from Cranwell Spa & Golf Club in Hancock, Hancock Village Inn at Jiminy Peak provides accommodations with access to a hot tub.
LanesboroughShow on map
Lakeside Berkshires Home Near Hiking and Skiing! offers accommodations in Lanesborough, 12 miles from Tanglewood and 12 miles from Cranwell Spa & Golf Club.
PittsfieldShow on map
Pittsfield Home with Deck - 12 Mi to Jiminy Peak! is located in Pittsfield, just 12 miles from Tanglewood and 12 miles from Cranwell Spa & Golf Club.
DaltonShow on map
Dalton Vacation Rental Near Hiking and Skiing! is located in Dalton, just 17 miles from Norman Rockwell Museum and 21 miles from The Clark Art Institute.
PittsfieldShow on map
Spacious Historic Home in the Berkshires! is located in Pittsfield, just 7.6 miles from Tanglewood and 7.8 miles from Cranwell Spa & Golf Club.
New LebanonShow on map
Historic New Lebanon Hideaway on 33 Private Acres! is located in New Lebanon, just 15 miles from Cranwell Spa & Golf Club and 15 miles from Tanglewood.
PittsfieldShow on map
Berkshire Vacation Rentals: Chic Pittsfield Home With A View is located in Pittsfield, just 7.1 miles from Tanglewood and 7.3 miles from Cranwell Spa & Golf Club.
WilliamstownShow on map
Berkshire Vacation Rentals: Renovated Five Bedrooms In Historic Williamstown is located in Williamstown, just 25 miles from Tanglewood and 26 miles from Cranwell Spa & Golf Club.
PittsfieldShow on map
Featuring an indoor swimming pool and a fitness center, Berkshire Mountain Lodge is located in Pittsfield. Free WiFi access is available in this lodge.
WilliamstownShow on map
Berkshire Vacation Rentals: The Brookman: Renovated 6000 SF Estate On 40 Acres offers accommodations in Williamstown, 19 miles from Bennington Battle Monument and 28 miles from Tanglewood.
WilliamstownShow on map
Luxury Vacation Rental in the Berkshires! offers accommodations in Williamstown, 18 miles from Bennington Battle Monument and 28 miles from Tanglewood.
WilliamstownShow on map
Peaceful Family Home with Fire Pit and Large Yard offers accommodations in Williamstown, 30 miles from Tanglewood and 30 miles from Cranwell Spa & Golf Club.
LenoxShow on map
Beautiful Lenox Home, 3 Mi to Shakespeare and Co! offers accommodations in Lenox, 3.7 miles from Cranwell Spa & Golf Club and 3.7 miles from Tanglewood Musical Center.
WilliamstownShow on map
North Getaway Cottage is located in Williamstown, just 29 miles from Cranwell Spa & Golf Club and 29 miles from Tanglewood Musical Center.
CanaanShow on map
Berkshire Vacation Rentals: Private Cottage Come Enjoy Nature is located in Canaan, just 8.9 miles from Tanglewood Musical Center and 9.3 miles from Tanglewood.
HinsdaleShow on map
Autumn Hill Lakehouse is located in Hinsdale, just 20 miles from Cranwell Spa & Golf Club and 20 miles from Tanglewood Musical Center. This vacation home features a garden.
LenoxShow on map
Restored 1881 Farm House offers accommodations in Lenox, 8.6 miles from Norman Rockwell Museum and 26 miles from The Clark Art Institute.
HinsdaleShow on map
Picturesque Cottage with Sunroom on Ashmere Lake! is located in Hinsdale, just 19 miles from Tanglewood and 20 miles from Cranwell Spa & Golf Club.
LenoxShow on map
Winthrop Estate 12K SF 32 Acres offers accommodations in Lenox, 1.5 miles from Tanglewood and 1.7 miles from Tanglewood Musical Center.
CheshireShow on map
27 miles from Tanglewood in Cheshire, Massachusetts Vacation Rental with Deck and Grill provides accommodations with access to a fitness room.