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Search results; 92 homes in Pittsfield

Guest favourite
Home in Pittsfield
Florence Guest House
3 bedrooms, 5 beds, 2 private bathrooms
16–21 Jul
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4.84 out of 5 average rating, 256 reviews
Superhost
Flat in Pittsfield
Dome View Loft
4.77 out of 5 average rating, 13 reviews, 2 bedrooms, 2 beds, 1 bathroom
23–28 Jul
Top guest favourite
Home in Pittsfield
Spacious whole house in Pittsfield!
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 5 beds, 2 bathrooms
17–22 Jul
Home in Pittsfield
Newly remodeled home
4.87 out of 5 average rating, 54 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
Guest favourite
Rooms in Pittsfield
Sloth Lodging (Upper Level)
4.91 out of 5 average rating, 53 reviews, 3 bedrooms, 3 beds, 1 bathroom
15–20 Jul
Guest favourite
Loft in Pittsfield
Historic Loft on Adams
4.9 out of 5 average rating, 94 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Guest favourite
Flat in Pittsfield
Pike County Haven: Retro Loft
5.0 out of 5 average rating, 21 reviews, 1 bedroom, 2 beds, 1 bathroom
15–20 Jul
Guest favourite
Home in Pittsfield Hill
Full Country Home Pittsfield, Illinois
4.94 out of 5 average rating, 31 reviews, 2 bedrooms, 4 beds, 1 bathroom
19–24 Jul
Bed and breakfast in Pittsfield
Premium King Suite | Boutique Stay + Private Bath
4.8 out of 5 average rating, 5 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Home in Griggsville
Arrowhead Farmhouse, Spacious home, scenic views
4.91 out of 5 average rating, 102 reviews, 3 bedrooms, 6 beds, 3 bathrooms
2–7 Aug
Cabin in Pittsfield
Cozy Country Cabin Perfect for Families & Retreats
4.74 out of 5 average rating, 19 reviews, 5 bedrooms, 8 beds, 5 bathrooms
27 Jul – 1 Aug
Top guest favourite
Home in New Canton
Comfortable farm house in the country
4.91 out of 5 average rating, 11 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Jul
Guest favourite
Home in Pittsfield
Modern Country Home Newly Remodeled
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 8 beds, 2 bathrooms
11–16 Aug
Hotel in Pittsfield
Quiet Queen Suite | Boutique Comfort, Private Bath
New place to stay, 1 bedroom, 1 bed, 1.5 bathrooms
16–21 Jul
Guest favourite
Home in Rockport
Red Rabbit Cottage #3
4.89 out of 5 average rating, 18 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Jul
Guest favourite
Cottage in Pearl
Beautiful Secluded Home With a breathtaking view
4.96 out of 5 average rating, 96 reviews, 3 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
Hotel in Pittsfield
Boutique Queen Suite I Private Bath + Fast WiFi
New place to stay, 1 bedroom, 1 bed, 1.5 bathrooms
16–21 Jul
Barn in Pleasant Hill
The Smithfarm barnloft
4.8 out of 5 average rating, 5 reviews, 2 bedrooms, 2 beds, 1 bathroom
15–20 Jul
Home in Winchester
Charming Country Retreat
New place to stay, 4 bedrooms, 5 beds, 1 bathroom
17–22 Jul