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
Home in Griggsville
4.88 out of 5 average rating, 76 reviewsArrowhead Farmhouse, Spacious home, scenic views
Feb 16 – 23
G$51,183 GYD per night
Guest favorite
Home in Winchester
4.94 out of 5 average rating, 48 reviewsWinchester Guest Cottage
Dec 28 – Jan 4
G$19,094 GYD per night
Guest favorite
Loft in Winchester
4.97 out of 5 average rating, 79 reviewsThe Bike Flat
Sep 13 – 20
G$21,278 GYD per night
Guest favorite
Vacation home in Meredosia
4.96 out of 5 average rating, 57 reviewsScenic 3 bedroom Wildlife Retreat
Jan 20 – 27
G$23,089 GYD per night
Guest favorite
Cottage in Pearl
4.99 out of 5 average rating, 67 reviewsBeautiful Secluded Home With a breathtaking view
Oct 13 – 20
G$44,608 GYD per night
Guest favorite
Home in White Hall
4.95 out of 5 average rating, 22 reviewsCozy-Rose-Cottage
Mar 23 – 30
G$18,447 GYD per night
Guest favorite
Home in Clarksville
4.94 out of 5 average rating, 53 reviewsMighty Mississippi Riverview - St. Louis Area
Jan 19 – 26
G$30,315 GYD per night
Superhost
Cabin in Louisiana
4.88 out of 5 average rating, 17 reviewsMississippi River Cabin
Jan 28 – Feb 4
G$21,610 GYD per night
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