Pittsfield vacation rentals

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Top-rated vacation rentals in Pittsfield

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Home in Pittsfield

Home With Modern Comforts & Rustic Berkshire Flare

Centrally located in the Berkshires, our inviting home sits on a safe and quiet street just a walk, ride, or drive from downtown Pittsfield. Warm up your day on the screened-in sun porch. Warm up your toes on the heated tile floors! Entertain in the open kitchen with custom concrete counters and wood floors throughout. Grill out on the rear patio while your dogs roam in the enclosed backyard. Hiking trails abound and playgrounds are just a stroll away. Relax, get cozy, and enjoy. You deserve it!

$115 per night

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Rental unit in Pittsfield

HawksNest: quiet 2BR apt, heart of the Berkshires

Soak up the Berkshires in a renovated 3rd floor apartment (private entrance, 2 flights up) that is well-appointed & homey w/ great views! Culture, skiing, nature, shopping, food & drinks just minutes away! But ALSO the urban amenities of Pittsfield: shops, dining, drinks...all in the Heart of the Berkshires! Located just off Hwy 7 (but very quiet!). 15 min=>Kripalu, Lenox & Tanglewood. 30 min=>Lee Outlets. 40 min=>Gr Barrington. 35 min=>MassMoca.

$70 per night

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Farm stay in Pittsfield

Private 2nd floor studio on a working produce farm

Charming 2nd floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums and much more. Visit our farm stand late June through mid October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or take a walk on our hiking trail.

$92 per night

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