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Vacation rentals in Pittsfield

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Top-rated holiday rentals in Pittsfield

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

Guest favourite
Home in Dalton
The Yellow House
The Yellow House in the Berkshires is the perfect place for a getaway, just 2. 5 hours from NYC and 2 hours from Boston. This historic small town offers many activities including Jacob's Pillow, hiking trails, skiing, Mass MoCA, and The Clark Art Institute. It is close to Tanglewood in Lenox and the Norman Rockwell Museum in Stockbridge. Located steps away from The Stationery Factory, which houses a food market, gallery spaces, artisan shops, coffee shop, and the Shire Brewhouse & pub.
30 Sept – 7 Oct
Guest favourite
Guest suite in Hancock
Cozy apartment near Jiminy Peak
Two cozy bedrooms with an efficient kitchen make this a great weekend getaway for 2 adults or family of 3 to use as a base to explore both north and south Berkshire county in every season. About a mile from Jiminy Peak Ski Resort, less than 5 minutes to Bloom Meadows, 15 minutes to both Williamstown and Pittsfield, and 30 minutes to Mass MoCA, the quiet, wooded mountainside surroundings let you enjoy nature at its finest while easily getting to the area's many cultural attractions.
18 – 25 Mar
Guest favourite
Earthen home in West Sand Lake
The Hobbit House at June Farms
Enjoy 120-acres of beautiful farmland while you stay in your very own Hobbit house! Nestled in the hills of Hudson Valley, June Farms is a gorgeous animal sanctuary. During your stay, you will be able to meet our Shire horses, Scottish highland cows, Gloucestershire spotted pigs, Nigerian dwarf goats, many chickens and ducks! From June 1 - Labor Day, the bar & restaurant is open most days for you to enjoy (check our calendar to be sure). We look forward to meeting you!
21 – 28 Nov

Popular amenities for Pittsfield holiday rentals

Stay near Pittsfield's top sights

Walmart9 locals recommend
Big Y World Class Market80 locals recommend
Berkshire Roots7 locals recommend
99 Restaurants7 locals recommend
Berkshire Museum102 locals recommend
Misty Moonlight Diner8 locals recommend

Other great holiday rentals in Pittsfield

Guest favourite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
5 – 12 Sept
Guest favourite
Apartment in Lenox
Station House 1E Private Room & Bath
9 – 16 May
Guest favourite
Home in Dalton
Brooksong, the perfect Berkshires getaway
10 – 17 Feb
Guest favourite
Treehouse in Tyringham
Gingerbread House Tower in the Berkshire Hills
3 – 10 June
Guest favourite
Apartment in Pittsfield
Marie's Place
8 – 15 June
Guest favourite
Apartment in Pittsfield
Simply off North
16 – 23 Sept
Guest favourite
Apartment in Canaan
Mountain View Getaway
21 – 28 Dec
Guest favourite
Apartment in Pittsfield
The Nest at Birdland
26 Nov – 3 Dec
Guest favourite
Apartment in Lanesborough
Cozy Rustic Apt. in 18th c. Berkshire Farmhouse
27 May – 3 June
Superhost
Apartment in Pittsfield
The Sunset Sanctuary - King Bed with Kitchen
26 Oct – 2 Nov
Guest favourite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
5 – 12 Aug
Superhost
Apartment in Pittsfield
Cozy Studio Apt in Downtown Victorian
12 – 19 May

Quick stats about holiday rentals in Pittsfield

Total rentals

210 properties

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

70 properties allow pets

Family-friendly rentals

110 properties are a good fit for families

Total number of reviews

6.9K reviews

Nightly prices starting at

$15 AUD before taxes and fees

Destinations to explore