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Search results; 95 homes in Pittsfield

Guest favourite
Guest suite in Pittsfield
Florence Guest House--Loft Unit
1 bedroom, 3 beds, 1 private bathroom
18–23 Sept
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4.81 out of 5 average rating, 140 reviews
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
Home in Pittsfield
Newly remodeled home
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
4.88 out of 5 average rating, 56 reviews
Guest favourite
Flat in Pittsfield
Pike County Haven Loft
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 22 reviews
Guest favourite
Loft in Pittsfield
Historic Loft on Adams
1 bedroom, 1 bed, 1 bathroom
17–22 Sept
4.87 out of 5 average rating, 98 reviews
Superhost
Flat in Pittsfield
Dome View Loft
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.8 out of 5 average rating, 15 reviews
Guest favourite
Rooms in Pittsfield
Sloth Lodging (Upper Level)
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.89 out of 5 average rating, 56 reviews
Guest favourite
Home in Pittsfield Hill
Full Country Home Pittsfield, Illinois
2 bedrooms, 4 beds, No bathroom
13–18 Sept
4.9 out of 5 average rating, 39 reviews
Hotel in Pittsfield
Boutique Queen Suite I Private Bath + Fast WiFi
1 bedroom, 1 bed, 1.5 bathrooms
20–25 Sept
Superhost
Flat in Pittsfield
The Retro Retreat
1 bedroom, 2 queen beds, 1 bathroom
10–15 Oct
New place to stay
Hotel in Pittsfield
Quiet Queen Suite | Boutique Comfort, Private Bath
1 bedroom, 1 bed, 1 bathroom
19–24 Sept
Superhost
Cabin in Belleview
Illinois Rustic Getaway!! Pike County,IL
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
4.81 out of 5 average rating, 27 reviews
Superhost
Cabin in Belleview
Illinois Rustic Getaway Lower Lodge
4 bedrooms, 8 beds, 2 bathrooms
13–18 Sept
4.89 out of 5 average rating, 9 reviews
Home in Versailles
The River House- A secluded paradise
2 bedrooms, 5 beds, 2 bathrooms
14–19 Sept
New place to stay
Guest house in Pittsfield
Private Guesthouse Queen Bed Washer Dryer Kitchen
1 bathroom
16–21 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
13–18 Sept
5.0 out of 5 average rating, 8 reviews
Room in Pittsfield
Premium King Suite | Boutique Stay + Private Bath
1 king bed, 1 bathroom
20–25 Sept
4.8 out of 5 average rating, 5 reviews
Guest favourite
Cabin in Mozier
Nature Escape-170 Country Acres
3 bedrooms, 7 beds, 2 bathrooms
1–6 Jan
5.0 out of 5 average rating, 9 reviews
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