Vacation rentals in Pittsfield
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Top-rated vacation rentals in Pittsfield
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Pittsfield vacation rentals
Other great vacation rentals in Pittsfield
Guest favorite
Guest suite in Lee
4.98 out of 5 average rating, 128 reviewsFarm setting. In-house suite with own entrance.
Jul 9 – 16
G$26,986 GYD per night
Guest favorite
Cottage in Middleton
4.96 out of 5 average rating, 136 reviewsBeautiful Lakeside Cottage
Dec 9 – 16
G$35,401 GYD per night
Guest favorite
Apartment in Tuftonboro
4.97 out of 5 average rating, 267 reviewsApartment CenterTuftonboro minutes from Wolfeboro
Nov 12 – 19
G$30,386 GYD per night
Guest favorite
Home in Pittsfield
4.94 out of 5 average rating, 17 reviewsCountry escape
May 15 – 22
G$16,985 GYD per night
Guest favorite
Farm stay in Epsom
5.0 out of 5 average rating, 73 reviewsAntq. Farm Ell-Private deck/views/trails/Dog yard!
Dec 11 – 18
G$33,246 GYD per night
Guest favorite
Cottage in Barrington
4.92 out of 5 average rating, 51 reviewsA little house in the woods
Mar 26 – Apr 2
G$23,144 GYD per night
Superhost
Cabin in Epsom
4.83 out of 5 average rating, 372 reviewsGetaway Blake Brook - Boston
Jun 1 – 8
G$37,747 GYD per night
Guest favorite
Home in Pittsfield
5.0 out of 5 average rating, 21 reviewsRestored Historic Colonial with Mountain Views
Oct 10 – 17
G$205,701 GYD per night
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