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Search results; 94 homes in Pittsfield

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Guest favourite
Home in Pittsfield
Florence Guest House
3 bedrooms, 5 beds, 2 private bathrooms
18–23 Sept
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4.84 out of 5 average rating, 256 reviews
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Top guest favourite
Home in Pittsfield
Spacious whole house in Pittsfield!
3 bedrooms, 5 beds
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
20–25 Sept
4.88 out of 5 average rating, 57 reviews
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Guest favourite
Rooms in Pittsfield
Sloth Lodging (Upper Level)
3 bedrooms, 3 beds
20–25 Sept
4.89 out of 5 average rating, 56 reviews
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Superhost
Flat in Pittsfield
Dome View Loft
2 bedrooms, 2 beds
17–22 Sept
4.8 out of 5 average rating, 15 reviews
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Guest favourite
Flat in Pittsfield
Pike County Haven Loft
1 bedroom, 2 beds
17–22 Sept
5.0 out of 5 average rating, 22 reviews
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Superhost
Loft in Pittsfield
Historic Loft on Adams
1 bedroom, 1 bed
18–23 Sept
4.87 out of 5 average rating, 98 reviews
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Top guest favourite
Home in Griggsville
Arrowhead Farmhouse, Spacious home, scenic views
3 bedrooms, 6 beds
27 Sept – 2 Oct
4.91 out of 5 average rating, 102 reviews
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Hotel in Pittsfield
Boutique Queen Suite I Private Bath + Fast WiFi
1 bedroom, 1 bed
20–25 Sept
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Hotel in Pittsfield
Quiet Queen Suite | Boutique Comfort, Private Bath
1 bedroom, 1 bed
19–24 Sept
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Home in Pittsfield
Modern Country Home Newly Remodeled
3 bedrooms, 8 beds
19–24 Sept
4.83 out of 5 average rating, 6 reviews
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Cabin in Pittsfield
Cozy Country Cabin Perfect for Families & Retreats
5 bedrooms, 8 beds
17–22 Sept
4.74 out of 5 average rating, 23 reviews
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Guest favourite
Home in Pittsfield Hill
Full Country Home Pittsfield, Illinois
2 bedrooms, 4 beds
16–21 Dec
4.9 out of 5 average rating, 40 reviews
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Room in Pittsfield
Premium King Suite | Boutique Stay + Private Bath
1 king bed
20–25 Sept
4.8 out of 5 average rating, 5 reviews
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Guest house in Pittsfield
Private Guesthouse Queen Bed Washer Dryer Kitchen
19–24 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
4–9 Oct
5.0 out of 5 average rating, 8 reviews
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Superhost
Flat in Pittsfield
The Retro Retreat
1 bedroom, 2 queen beds
8–13 Nov
New place to stay
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Top guest favourite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 bedroom, 1 king bed
26 Sept – 1 Oct
4.97 out of 5 average rating, 200 reviews
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Guest favourite
Guest suite in Pittsfield
Florence Guest House--Loft Unit
1 bedroom, 3 beds
18–23 Sept
4.81 out of 5 average rating, 140 reviews