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Search results; 97 homes in Pittsfield

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Guest favourite
Home in Pittsfield
Florence Guest House
3 bedrooms, 5 beds, 2 private bathrooms
21–26 Sept
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4.84 out of 5 average rating, 257 reviews
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Top guest favourite
Home in Pittsfield
Spacious whole house in Pittsfield!
3 bedrooms, 5 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 10 reviews
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Home in Pittsfield
Newly remodeled home
2 bedrooms, 2 queen beds, 1 bathroom
21–26 Sept
4.88 out of 5 average rating, 58 reviews
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Guest favourite
Flat in Pittsfield
Pike County Haven Loft
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 22 reviews
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Superhost
Flat in Pittsfield
Dome View Loft
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.8 out of 5 average rating, 15 reviews
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Superhost
Loft in Pittsfield
Historic Loft on Adams
1 bedroom, 1 bed, 1 bathroom
21–26 Sept
4.87 out of 5 average rating, 98 reviews
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Guest favourite
Rooms in Pittsfield
Sloth Lodging (Upper Level)
3 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.89 out of 5 average rating, 56 reviews
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Hotel in Pittsfield
Boutique Queen Suite I Private Bath + Fast WiFi
1 bedroom, 1 bed, 1.5 bathrooms
20–25 Sept
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Superhost
Flat in Pittsfield
The Retro Retreat
1 bedroom, 2 queen beds, 1 bathroom
8–13 Nov
New place to stay
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Hotel in Pittsfield
Historic Boutique Stay | Cozy Queen Suite
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
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Home in Pittsfield
Modern Country Home Newly Remodeled
3 bedrooms, 8 beds, 2 bathrooms
22–27 Sept
4.83 out of 5 average rating, 6 reviews
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Guest favourite
Home in Pittsfield Hill
Full Country Home Pittsfield, Illinois
2 bedrooms, 4 beds, No bathroom
11–16 Oct
4.9 out of 5 average rating, 40 reviews
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Top guest favourite
Home in Griggsville
Arrowhead Farmhouse, Spacious home, scenic views
3 bedrooms, 6 beds, 3 bathrooms
27 Sept – 2 Oct
4.91 out of 5 average rating, 102 reviews
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Hotel in Pittsfield
Quiet Queen Suite | Boutique Comfort, Private Bath
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
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Cabin in Pittsfield
Cozy Country Cabin Perfect for Families & Retreats
5 bedrooms, 8 beds, 5 bathrooms
20–25 Sept
4.74 out of 5 average rating, 23 reviews
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Guest house in Pittsfield
Private Guesthouse Queen Bed Washer Dryer Kitchen
1 bathroom
22–27 Sept
4.78 out of 5 average rating, 27 reviews
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Guest favourite
Guest suite in Barry
The Hideaway at Howard Farms
2 bedrooms, 1 queen bed, 2 bathrooms
11–16 Oct
5.0 out of 5 average rating, 8 reviews
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Barn in Pleasant Hill
The Smithfarm barnloft
2 bedrooms, 2 beds, 1 bathroom
28 Sept – 3 Oct
4.83 out of 5 average rating, 6 reviews
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Home in Mount Sterling
Idyllic Mt Sterling Retreat w/ Private Lake!
4 bedrooms, 13 beds, 2.5 bathrooms
10–15 Dec
4.84 out of 5 average rating, 37 reviews