Search results; 328 homes in Pittsfield

Top guest favorite
Loft in Pittsfield
Historic Loft on Adams
Free cancellation
Oct 4 – 9
ﺩ.ﺇ1,550 for 5 nights
4.92 out of 5 average rating, 75 reviews
Guest favorite
Home in Pittsfield
Roots Lodge at Pittsfield Lake (Starlink Internet)
Free cancellation
Aug 3 – 8
ﺩ.ﺇ2,618 for 5 nights
4.91 out of 5 average rating, 23 reviews
Top guest favorite
Home in Pittsfield
Newly remodeled home
Free cancellation
Aug 3 – 8
ﺩ.ﺇ2,992 for 5 nights
5.0 out of 5 average rating, 37 reviews
Top guest favorite
Apartment in Pittsfield
Pike County Haven: Retro Loft
Free cancellation
Aug 20 – 25
ﺩ.ﺇ1,873 for 5 nights
5.0 out of 5 average rating, 8 reviews
Guest favorite
Home in Pittsfield
Florence Guest House
5 beds
Aug 1 – 6
ﺩ.ﺇ1,507 for 5 nights
4.85 out of 5 average rating, 243 reviews
Top guest favorite
Home in Griggsville
Arrowhead Farmhouse, Spacious home, scenic views
Free cancellation
Aug 17 – 22
ﺩ.ﺇ5,317 for 5 nights
4.9 out of 5 average rating, 92 reviews
Top guest favorite
Home in Winchester
Winchester Guest Cottage
Free cancellation
Aug 3 – 8
ﺩ.ﺇ1,916 for 5 nights
4.92 out of 5 average rating, 145 reviews
Guest favorite
Guest suite in Pittsfield
Florence Guest House--Loft Unit
Free cancellation
Aug 2 – 7
ﺩ.ﺇ1,400 for 5 nights
4.82 out of 5 average rating, 134 reviews
Guest favorite
Room in Pittsfield
Stay with SteveHosting for 6 years,
Sloth Lodging (Upper Level)
Aug 16 – 21
ﺩ.ﺇ1,516 for 5 nights
4.86 out of 5 average rating, 37 reviews
Guesthouse in Pittsfield
Private Guesthouse Kitchen Washer Dryer New Queen
Aug 1 – 6
ﺩ.ﺇ1,852 for 5 nights
4.74 out of 5 average rating, 23 reviews
Guest favorite
Loft in Winchester
The Bike Flat
5 beds
Aug 3 – 8
ﺩ.ﺇ2,183 for 5 nights
4.95 out of 5 average rating, 129 reviews
Top guest favorite
Home in Meredosia
The Fricke Farm
Free cancellation
Aug 3 – 8
ﺩ.ﺇ2,992 for 5 nights
5.0 out of 5 average rating, 30 reviews
Home in Pittsfield
Modern Country Home Newly Remodeled
8 beds
Aug 1 – 6
ﺩ.ﺇ4,736 for 5 nights
5.0 out of 5 average rating, 4 reviews
Guest favorite
Cabin in Pittsfield
Cozy Country Cabin Perfect for Families & Retreats
8 beds
Aug 19 – 24
ﺩ.ﺇ8,772 for 5 nights
5.0 out of 5 average rating, 8 reviews
Top guest favorite
Cabin in Winchester
Container Home GREAT Countryside Views COZY Stay
1 king bed
Aug 1 – 6
ﺩ.ﺇ2,045 for 5 nights
4.96 out of 5 average rating, 167 reviews
Top guest favorite
Cabin in Jacksonville
Bunkhouse Seventy-Four
Free cancellation
Aug 2 – 7
ﺩ.ﺇ1,916 for 5 nights
4.97 out of 5 average rating, 348 reviews
Home in Winchester
The "Craft"men's House
Free cancellation
Aug 1 – 6
ﺩ.ﺇ2,067 for 5 nights
New place to stay
Superhost
Cabin in Hillview
Modern-Rustic Cabin on 2 Acres- Nature Inspired
2 beds
Aug 1 – 6
ﺩ.ﺇ2,546 for 5 nights, originally ﺩ.ﺇ2,747
4.98 out of 5 average rating, 40 reviews