Skip to content

Pittsfield vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Pittsfield

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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
SUPERHOST
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
SUPERHOST
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
SUPERHOST

Stay near Pittsfield's top sights

Photo of Walmart
Walmart9 locals recommend
Photo of Berkshire Roots
Berkshire Roots7 locals recommend
Photo of Ashuwillticook Rail Trail
Ashuwillticook Rail Trail74 locals recommend
Photo of Big Y World Class Market
Big Y World Class Market81 locals recommend
Photo of 99 Restaurants
99 Restaurants7 locals recommend
Photo of Market32
Market3219 locals recommend

Other great vacation rentals in Pittsfield

Guesthouse in Lenox
The Granary at House on Golden Hill
$90 per night
SUPERHOST
Rental unit in Pittsfield
Simply off North
$98 per night
SUPERHOST
Rental unit in Pittsfield
Sharon's Place 4 .....420 friendly!!!!
$53 per night
Rental unit in Pittsfield
Cozy 2-Bedroom Apartment - Close to downtown!
$107 per night
SUPERHOST
Rental unit in Lanesborough
Lovely studio minutes from Jiminy Peak
$111 per night
Private room in Dalton
Dalton in the Beautiful Berkshires
$65 per night
SUPERHOST
Rental unit in Pittsfield
Charming Apartment In Berkshire Victorian Home
$123 per night
SUPERHOST
Rental unit in Pittsfield
Sharon's Place 5 420 friendly!!!!!!
$67 per night
Rental unit in Lenox
Main Street Delight - One Bedroom Apartment
$218 per night
SUPERHOST
Home in Dalton
The Yellow House
$93 per night
SUPERHOST
Rental unit in Pittsfield
Lovely 1-bdrm unit with free parking on premises
$60 per night
Private room in Pittsfield
Large guest suite w/private bath in the Berkshires
$91 per night
SUPERHOST