Holiday 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.
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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
Flat in Pittsfield
4.92 out of 5 average rating, 25 reviewsComfortable Pittsfield Loft
7–14 Nov
£74 per night
Superhost
Flat in Pittsfield
4.86 out of 5 average rating, 42 reviewsThe Sunset Sanctuary - King Bed with Kitchen
15–22 Mar
£65 per night
Superhost
Flat in Pittsfield
4.83 out of 5 average rating, 18 reviewsCozy Studio Apt in Downtown Victorian
29 Jun – 6 Jul
£118 per night
Guest favourite
Flat in Pittsfield
5.0 out of 5 average rating, 41 reviewsSimply off North
10–17 Nov
£80 per night
Guest favourite
Guest house in Pittsfield
4.98 out of 5 average rating, 47 reviewsThe Nest at Birdland
11–18 Oct
£154 per night
Guest favourite
Flat in Pittsfield
4.96 out of 5 average rating, 48 reviewsThe sweet place in the beautiful Berkshires!
7–14 Dec
£118 per night
Superhost
Cottage in Pittsfield
4.9 out of 5 average rating, 69 reviewsCottage Getaway - access all the Berkshires offer!
28 May – 4 Jun
£136 per night
Guest favourite
Flat in Canaan
5.0 out of 5 average rating, 83 reviewsMountain View Getaway
27 Aug – 3 Sept
£95 per night
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
£8 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
- Pet-friendly rentals Pittsfield
- Monthly Rentals Pittsfield
- Rentals with a firepit Pittsfield
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- Rentals with a washing machine and dryer Pittsfield
- House rentals Pittsfield
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