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Search results; 91 homes in Pittsfield

Top guest favourite
Home in Pittsfield
Florence Guest House
3 bedrooms, 5 beds, 2 private bathrooms
8–13 Jul
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4.85 out of 5 average rating, 254 reviews
Guest favourite
Loft in Pittsfield
Historic Loft on Adams
1 bedroom, 1 bed, 1 bathroom
6–11 Jul
4.9 out of 5 average rating, 94 reviews
Top guest favourite
Home in Pittsfield
Spacious whole house in Pittsfield!
3 bedrooms, 5 beds, 2 bathrooms
9–14 Jul
5.0 out of 5 average rating, 7 reviews
Guest favourite
Flat in Pittsfield
Dome View Loft
2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
4.75 out of 5 average rating, 12 reviews
Guest favourite
Home in Pittsfield Hill
Full Country Home Pittsfield, Illinois
2 bedrooms, 4 beds, 1 bathroom
19–24 Jul
4.97 out of 5 average rating, 29 reviews
Guest favourite
Rooms in Pittsfield
Sloth Lodging (Upper Level)
3 bedrooms, 3 beds, 1 bathroom
6–11 Jul
4.91 out of 5 average rating, 53 reviews
Guest favourite
Flat in Pittsfield
Pike County Haven: Retro Loft
1 bedroom, 2 beds, 1 bathroom
1–6 Sept
5.0 out of 5 average rating, 21 reviews
Superhost
Home in Pittsfield
Newly remodeled home
2 bedrooms, 2 queen beds, 1 bathroom
7–12 Jul
4.87 out of 5 average rating, 54 reviews
Hotel in Pittsfield
Charming Boutique Retreat | 2 Twins + Private Bath
1 bedroom, 2 single beds, 1.5 bathrooms
6–11 Jul
New place to stay
Top guest favourite
Home in New Canton
Comfortable farm house in the country
1 bedroom, 2 beds, 1 bathroom
7–12 Jul
4.91 out of 5 average rating, 11 reviews
Hotel in Pittsfield
Boutique Queen Suite I Private Bath + Fast WiFi
1 bedroom, 1 bed, 1.5 bathrooms
16–21 Jul
New place to stay
Superhost
Cabin in Pittsfield
Cozy Country Cabin Perfect for Families & Retreats
5 bedrooms, 8 beds, 5 bathrooms
27 Jul – 1 Aug
4.78 out of 5 average rating, 18 reviews
Hotel in Pittsfield
Quiet Queen Suite | Boutique Comfort, Private Bath
1 bedroom, 1 bed, 1.5 bathrooms
6–11 Jul
New place to stay
Guest house in Pittsfield
Private Guesthouse Queen Bed Washer Dryer Kitchen
1 bathroom
12–17 Jul
4.78 out of 5 average rating, 27 reviews
Guest favourite
Loft in Winchester
The Bike Flat
2 bedrooms, 5 beds, 1 bathroom
9–14 Aug
4.93 out of 5 average rating, 174 reviews
Top guest favourite
Home in Griggsville
Arrowhead Farmhouse, Spacious home, scenic views
3 bedrooms, 6 beds, 3 bathrooms
7–12 Jul
4.91 out of 5 average rating, 102 reviews
Home in Mount Sterling
Idyllic Mt Sterling Retreat w/ Private Lake!
4 bedrooms, 13 beds, 2.5 bathrooms
18–23 Aug
4.84 out of 5 average rating, 32 reviews
Barn in Pleasant Hill
The Smithfarm barnloft
2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 3 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