Holiday houses in Pittsfield
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Pittsfield
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
1 of 3 pages
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Pittsfield holiday rentals
Other great holiday rentals in Pittsfield
Guest favourite
Cabin in Cheshire
4.9 out of 5 average rating, 153 reviewsPrivate Paradise in the Berkshires
Guest favourite
Cottage in Lanesborough
4.92 out of 5 average rating, 223 reviewsStone School Cottage
Guest favourite
Home in Chester
4.96 out of 5 average rating, 316 reviewsRiverfront Getaway
Guest favourite
Tiny home in Chatham
4.99 out of 5 average rating, 188 reviewsTiny House on 70 Private Acres in Hudson Valley
Guest favourite
Cottage in Kinderhook
4.98 out of 5 average rating, 180 reviewsThe Cottage on Sylvester Street
Guest favourite
Apartment in Pittsfield
4.9 out of 5 average rating, 29 reviewsComfortable Pittsfield Loft
Guest favourite
Apartment in Pittsfield
4.96 out of 5 average rating, 52 reviewsThe sweet place in the beautiful Berkshires!
Superhost
Apartment in Pittsfield
4.78 out of 5 average rating, 9 reviewsCozy Chic - Studio Apartment
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
120 properties are a good fit for families
Total number of reviews
7.1K reviews
Nightly prices starting at
$16 NZD before taxes and fees
Destinations to explore
- New City Holiday rentals
- New Haven Holiday rentals
- Lake George Holiday rentals
- Catskill Holiday rentals
- Albany Holiday rentals
- Catskill Mountains Holiday rentals
- Philadelphia Holiday rentals
- New York Holiday rentals
- Jersey City Holiday rentals
- The Hamptons Holiday rentals
- Boston Holiday rentals
- Montreal Holiday rentals
- Rentals with a washing machine and dryer Pittsfield
- Rentals with pools Pittsfield
- Kid-friendly rentals Pittsfield
- Waterfront rentals Pittsfield
- Pet-friendly rentals Pittsfield
- Family-friendly rentals Pittsfield
- Rentals with a fireplace Pittsfield
- Rentals with a patio Pittsfield
- Rentals with a fire pit Pittsfield
- Rentals with outdoor seating Pittsfield
- Apartment rentals Pittsfield
- House rentals Pittsfield
- Rentals with lake access Pittsfield
- Monthly Rentals Pittsfield
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom