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Search results; 96 homes in Pittsfield

Guest favourite
Home in Pittsfield
Florence Guest House
3 bedrooms, 5 beds, 2 private bathrooms
6–11 Oct
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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
6–11 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Flat in Pittsfield
Pike County Haven Loft
1 bedroom, 2 beds, 1 bathroom
3–8 Sept
5.0 out of 5 average rating, 22 reviews
Superhost
Flat in Pittsfield
Dome View Loft
2 bedrooms, 2 beds, 1 bathroom
3–8 Sept
4.8 out of 5 average rating, 15 reviews
Home in Pittsfield
Newly remodeled home
2 bedrooms, 2 queen beds, 1 bathroom
8–13 Sept
4.88 out of 5 average rating, 56 reviews
Superhost
Loft in Pittsfield
Historic Loft on Adams
1 bedroom, 1 bed, 1 bathroom
4–9 Sept
4.87 out of 5 average rating, 97 reviews
Superhost
Flat in Pittsfield
The Retro Retreat
1 bedroom, 2 queen beds, 1 bathroom
10–15 Oct
New place to stay
Guest favourite
Rooms in Pittsfield
Sloth Lodging (Upper Level)
3 bedrooms, 3 beds, 1 bathroom
5–10 Sept
4.89 out of 5 average rating, 55 reviews
Room in Pittsfield
Quiet Queen Suite | Boutique Comfort, Private Bath
1 bed, 1.5 bathrooms
6–11 Sept
Guest favourite
Home in Pittsfield Hill
Full Country Home Pittsfield, Illinois
2 bedrooms, 4 beds, No bathroom
6–11 Sept
4.9 out of 5 average rating, 39 reviews
Cabin in Pittsfield
Cozy Country Cabin Perfect for Families & Retreats
5 bedrooms, 8 beds, 5 bathrooms
7–12 Sept
4.74 out of 5 average rating, 23 reviews
Room in Pittsfield
Boutique Queen Suite I Private Bath + Fast WiFi
1 bed, 1.5 bathrooms
6–11 Sept
Guest house in Pittsfield
Private Guesthouse Queen Bed Washer Dryer Kitchen
1 bathroom
9–14 Sept
4.78 out of 5 average rating, 27 reviews
Guest favourite
Guest suite in Barry
The Hideaway at Howard Farms
2 bedrooms, 1 queen bed, 2 bathrooms
3–8 Sept
5.0 out of 5 average rating, 8 reviews
Room in Pittsfield
Premium King Suite | Boutique Stay + Private Bath
1 bed, 1 bathroom
6–11 Sept
4.8 out of 5 average rating, 5 reviews
Home in Barry
Historic Barry House
6 bedrooms, 10 beds, 2 bathrooms
18–23 Sept
4.25 out of 5 average rating, 16 reviews
Superhost
Home in Louisiana
The Yellow Rose Historic Home
4 bedrooms, 10 beds, 2 bathrooms
7–12 Sept
4.93 out of 5 average rating, 54 reviews
Guest suite in Hamburg
Suite 1 | 3BR Home, Sleeps 6, Wi-Fi, W/D, Kitchen
3 bedrooms, 4 beds, 1 bathroom
8–13 Sept
Home in Versailles
The River House- A secluded paradise
2 bedrooms, 5 beds, 2 bathrooms
14–19 Sept
New place to stay