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Search results; 88 homes in Pittsfield

Guest favourite
Home in Pittsfield
Florence Guest House
3 bedrooms, 5 beds, 2 private bathrooms
17–22 Sept
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4.84 out of 5 average rating, 256 reviews
Top guest favourite
Home in Pittsfield
Spacious whole house in Pittsfield!
3 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 9 reviews
Home in Pittsfield
Newly remodeled home
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.87 out of 5 average rating, 55 reviews
Guest favourite
Rooms in Pittsfield
Sloth Lodging (Upper Level)
3 bedrooms, 3 beds, 1 bathroom
4–9 Aug
4.91 out of 5 average rating, 54 reviews
Guest favourite
Flat in Pittsfield
Pike County Haven: Retro Loft
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 21 reviews
Guest favourite
Loft in Pittsfield
Historic Loft on Adams
1 bedroom, 1 bed, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 95 reviews
Superhost
Flat in Pittsfield
Dome View Loft
2 bedrooms, 2 beds, 1 bathroom
1–6 Feb
4.8 out of 5 average rating, 15 reviews
Room in Pittsfield
Boutique Queen Suite I Private Bath + Fast WiFi
1 bed, 1.5 bathrooms
16–21 Aug
New place to stay
Cabin in Pittsfield
Cozy Country Cabin Perfect for Families & Retreats
5 bedrooms, 8 beds, 5 bathrooms
11–16 Aug
4.73 out of 5 average rating, 22 reviews
Guest favourite
Home in Pittsfield Hill
Full Country Home Pittsfield, Illinois
2 bedrooms, 4 beds, No bathroom
16–21 Aug
4.94 out of 5 average rating, 32 reviews
Guest favourite
Home in Pittsfield
Modern Country Home Newly Remodeled
3 bedrooms, 8 beds, 2 bathrooms
11–16 Aug
5.0 out of 5 average rating, 5 reviews
Room in Pittsfield
Premium King Suite | Boutique Stay + Private Bath
1 bed, 1 bathroom
9–14 Aug
4.8 out of 5 average rating, 5 reviews
Top guest favourite
Home in Griggsville
Arrowhead Farmhouse, Spacious home, scenic views
3 bedrooms, 6 beds, 3 bathrooms
8–13 Sept
4.91 out of 5 average rating, 102 reviews
Barn in Pleasant Hill
The Smithfarm barnloft
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
4.83 out of 5 average rating, 6 reviews
Room in Pittsfield
Quiet Queen Suite | Boutique Comfort, Private Bath
1 bed, 1.5 bathrooms
9–14 Aug
New place to stay
Home in Winchester
Charming Country Retreat
4 bedrooms, 5 beds, 1 bathroom
6–11 Aug
New place to stay
Guest house in Pittsfield
Private Guesthouse Queen Bed Washer Dryer Kitchen
1 bathroom
16–21 Aug
4.78 out of 5 average rating, 27 reviews
Top guest favourite
Home in New Canton
Comfortable farm house in the country
1 bedroom, 2 beds, 1 bathroom
10–15 Aug
4.91 out of 5 average rating, 11 reviews
Guest favourite
Home in Bowling Green
Cozy blue home
2 bedrooms, 3 beds, 1 bathroom
13–18 Aug
4.89 out of 5 average rating, 46 reviews