119 places in Winchester

Guest favorite
Home in Winchester
Winchester Guest Cottage
2 beds
May 5 – 10
4.93 out of 5 average rating, 43 reviews
Guest favorite
Loft in Winchester
The Bike Flat
5 beds
Apr 14 – 19
4.97 out of 5 average rating, 77 reviews
Guest favorite
Apartment in Winchester
Sugar Shack, a retro studio apartment
1 queen bed
Apr 1 – 6
4.88 out of 5 average rating, 40 reviews
Guest favorite
Cabin in Jacksonville
Audrey's Abode
4 beds
Apr 8 – 13
4.97 out of 5 average rating, 614 reviews
Guest favorite
Cabin in Jacksonville
Bunkhouse Seventy-Four
1 queen bed
Apr 9 – 14
4.97 out of 5 average rating, 271 reviews
Guest favorite
Apartment in Winchester
The Primrose inside historic commercial bldg
3 beds
May 1 – 6
4.97 out of 5 average rating, 67 reviews
Guest favorite
Vacation home in Meredosia
Scenic 3 bedroom Wildlife Retreat
5 beds
Apr 1 – 6
4.96 out of 5 average rating, 55 reviews
Guest favorite
Home in Griggsville
Arrowhead Farmhouse, Spacious home, scenic views
6 beds
Apr 1 – 6
4.88 out of 5 average rating, 76 reviews
Guest favorite
Apartment in Murrayville
Peace on the Prairie - Studio Apartment
4 beds
Apr 1 – 6
4.97 out of 5 average rating, 381 reviews
Guest favorite
Cottage in Pearl
Beautiful Secluded Home With a breathtaking view
5 beds
Apr 9 – 14
4.98 out of 5 average rating, 66 reviews
Guest favorite
Townhouse in Murrayville
Peace on the Prairie Too - Tiny House
3 beds
Apr 9 – 14
4.98 out of 5 average rating, 262 reviews
Guest favorite
Home in Beardstown
My Little Bungalow on Monroe Street.
5 beds
Apr 2 – 7
4.99 out of 5 average rating, 155 reviews
Guest favorite
Home in Jacksonville
1.5 bath,laundry,DW,Netflix,HS Wi-Fi,deck,ext.stay
2 beds
Apr 1 – 6
5.0 out of 5 average rating, 5 reviews
Guest favorite
Home in Pittsfield
Newly remodeled home
2 queen beds
Apr 1 – 6
5.0 out of 5 average rating, 8 reviews
Guest favorite
Home in White Hall
Cozy-Rose-Cottage
3 beds
Apr 1 – 6
4.95 out of 5 average rating, 20 reviews
Home in Roodhouse
Cozy Corner Bungalow
4 beds
Apr 1 – 6
5.0 out of 5 average rating, 3 reviews
Guest favorite
Home in Pittsfield
Florence Guest House
5 beds
Apr 1 – 6
4.83 out of 5 average rating, 201 reviews
Superhost
Guest suite in Pittsfield
Florence Guest House--Loft Unit
3 beds
Apr 1 – 6
4.8 out of 5 average rating, 115 reviews