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Search results; 234 homes in Gillespie

Guest favourite
Home in Staunton
2br home, private yard hot tub
2 bedrooms, 2 beds, 1 bathroom
26 Sept – 1 Oct
4.88 out of 5 average rating, 156 reviews
Top guest favourite
Home in Litchfield
State Street House- Pets welcome; Litchfield
3 bedrooms, 3 beds, 2 bathrooms
18–23 Sept
4.96 out of 5 average rating, 73 reviews
Guest favourite
Home in Mount Olive
Relaxing Fishing Cabin
2 bedrooms, 3 beds, 1 bathroom
6–11 Nov
4.93 out of 5 average rating, 82 reviews
Guest favourite
Flat in Litchfield
The State Street Loft | Small Town Charm
3 bedrooms, 3 beds, 1.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 39 reviews
Top guest favourite
Home in Litchfield
Harrison House; PETS WELCOME; FENCED YARD
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Sept
4.96 out of 5 average rating, 321 reviews
Guest favourite
Flat in Litchfield
The State Street Loft II | Downtown Retreat
3 bedrooms, 4 beds, 2 bathrooms
17–22 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Guest house in Plainview
Sip & Stay Vineyard Getaway
3 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Mount Olive
Lake House off Route 66
1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.87 out of 5 average rating, 109 reviews
Home in Litchfield
Route 66 Gem! Charming Litchfield Home w/ Yard
3 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
4.47 out of 5 average rating, 15 reviews
Top guest favourite
Home in Carlinville
The Campground House
3 bedrooms, 4 beds, 2 bathrooms
12–17 Oct
4.97 out of 5 average rating, 122 reviews
Guest favourite
Home in Hillsboro
Hillsboro Home
3 bedrooms, 4 beds, 1 bathroom
24–29 Nov
4.95 out of 5 average rating, 38 reviews
Guest favourite
Dome in Worden
Glamping Dome: Bunks, Hot Tub, Brewery & Farm Fun
1 bedroom, 5 beds, No bathroom
15–20 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Room in Carlinville
Charming private room in shared house on Rt. 66
1 queen bed, 1.5 bathrooms
15–20 Sept
4.98 out of 5 average rating, 51 reviews
Dome in Worden
Family Dome: Hot Tub, Farm Fun, Brewery & Pizza
1 bedroom, 2 queen beds, No bathroom
15–20 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Hillsboro
Historic stay at the 1843 Blackman-Evans Home /4BR
4 bedrooms, 6 beds, 2 bathrooms
18–23 Sept
4.89 out of 5 average rating, 62 reviews
Dome in Worden
Romantic Dome: Private Hot Tub + Brewery & Pizza
1 bedroom, 1 king bed, No bathroom
19–24 Sept
5.0 out of 5 average rating, 4 reviews
Tiny home in Worden
Cozy Tiny House: Brewery & Pizza on the Farm
1 bedroom, 2 beds, No bathroom
20–25 Sept
Guest favourite
Home in Carlinville
The Carlinville Cottage
3 bedrooms, 6 beds, 2 bathrooms
5–10 Oct
4.96 out of 5 average rating, 53 reviews