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72 properties are available in and around this destination
WilliamstownShow on map3.2 miles from map center
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.
WilliamstownShow on map4.2 miles from map center
Luxury Vacation Rental in the Berkshires! offers accommodations in Williamstown, 18 miles from Bennington Battle Monument and 28 miles from Tanglewood.
WilliamstownShow on map4.5 miles from map center
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.
WilliamstownShow on map5.2 miles from map center
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.
HancockShow on map6.4 miles from map center
20 miles from Tanglewood in Hancock, Mountainside Condo @ Jiminy Peak in the Berkshires offers accommodations with access to a hot tub.
HancockShow on map6.4 miles from map center
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 map6.6 miles from map center
Spacious 3BR 3BA Sleeps 8 Ski On Off Jiminy Mountain Resort offers accommodations in Hancock, 21 miles from Tanglewood and 21 miles from Cranwell Spa & Golf Club.
HancockShow on map6.6 miles from map center
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 map8.2 miles from map center
23 miles from Cranwell Spa & Golf Club in Hancock, Hancock Village Inn at Jiminy Peak provides accommodations with access to a hot tub.
North AdamsShow on map8.7 miles from map center
Featuring a garden, a terrace as well as a bar, The Lodge @ America’s Switzerland is located in North Adams, within 25 miles of Bennington Battle Monument and 10 miles of The Clark Art Institute.
LanesboroughShow on map9.1 miles from map center
Lakeside Berkshires Home Near Hiking and Skiing! offers accommodations in Lanesborough, 12 miles from Tanglewood and 12 miles from Cranwell Spa & Golf Club.
FloridaShow on map10.1 miles from map center
Offering a garden, Florida Mountain Log Cabin features accommodations in Florida. This property offers access to a terrace and free private parking.
PittsfieldShow on map11 miles from map center
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.
PittsfieldShow on map11.4 miles from map center
A recently renovated vacation home, Cute Cape Cod Style Home offers accommodations in Pittsfield. This vacation home provides free private parking, private check-in and check-out, and free Wifi.
DaltonShow on map11.4 miles from map center
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.
CheshireShow on map12 miles from map center
27 miles from Tanglewood in Cheshire, Massachusetts Vacation Rental with Deck and Grill provides accommodations with access to a fitness room.
PittsfieldShow on map13.3 miles from map center
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.
BenningtonShow on map14 miles from map center
Bennington Cabin with Deck and Views of 3 States! offers accommodations in Bennington, 31 miles from Rensselaer Polytechnic Institute.
HinsdaleShow on map14 miles from map center
Autumn Hill Lakehouse offers accommodations in Hinsdale, 20 miles from Cranwell Spa & Golf Club and 20 miles from Tanglewood Musical Center.
HinsdaleShow on map14.4 miles from map center
Picturesque Cottage with Sunroom on Ashmere Lake! is located in Hinsdale, just 19 miles from Tanglewood and 20 miles from Cranwell Spa & Golf Club.
PittsfieldShow on map14.4 miles from map center
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.
BenningtonShow on map14.6 miles from map center
5.6 miles from Bennington Battle Monument in Bennington, Two Brooks Lodge features accommodations with access to a hot tub. Guests can benefit from a patio and a picnic area.
CharlemontShow on map14.6 miles from map center
Charlemont Retreat on Chickley River with EV Charger offers accommodations in Charlemont, 27 miles from The Clark Art Institute. This vacation home provides air-conditioned accommodations with a...
HawleyShow on map14.6 miles from map center
Providing a garden, 12-Acre Vacation Rental in the Berkshires! offers accommodations in Hawley. The air-conditioned accommodation is 27 miles from The Clark Art Institute.
New LebanonShow on map15.1 miles from map center
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.
