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Search results; Over 1,000 homes in Woodstock

Guest favourite
Flat in Woodstock
Historic Apartment on the Woodstock Square
2 bedrooms, 2 beds, 1 private bathroom
1–6 Nov
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4.86 out of 5 average rating, 310 reviews
Guest favourite
Home in Woodstock
The Tailor House: 2BR w/ Hot Tub near Woodstock Sq
2 bedrooms, 3 beds, 1.5 bathrooms
28 Sept – 3 Oct
4.94 out of 5 average rating, 286 reviews
Guest favourite
Flat in Woodstock
Cute private apartment 0.6mi from Woodstock Square
1 bedroom, 1 king bed, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Woodstock
Finally… A Home Big Enough for Everyone 8 Beds
5 bedrooms, 8 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Loft in Woodstock
Curated Loft Retreat in The Heart Of Woodstock
1 bedroom, 1 queen bed, 1 bathroom
26 Sept – 1 Oct
4.97 out of 5 average rating, 231 reviews
Home in Woodstock
Woods at Woodstock
3 bedrooms, 4 beds, 2 bathrooms
19–24 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Woodstock
Cute apartment near the Historic Woodstock Square
1 bedroom, 3 beds, 1 bathroom
10–15 Sept
4.98 out of 5 average rating, 58 reviews
Bed and breakfast in Woodstock
Old Oak Suite @ Cherry Tree Inn B&B
1 bedroom, 2 queen beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 9 reviews
Guest favourite
Loft in Woodstock
The Lux Loft~Walk to Square/Train Link to Chicago
2 bedrooms, 2 beds, 1 bathroom
3–8 Jan
4.99 out of 5 average rating, 77 reviews
Home in Algonquin
Private Woodland Suite • Fireplace • Near Downtown
1 bedroom, 2 beds, 1 bathroom
19–24 Oct
New place to stay
Top guest favourite
Home in Crystal Lake
-NEW- Blue Magnolia Cottage -3 King Beds- Luxury
4 bedrooms, 5 beds, 2.5 bathrooms
2–7 Oct
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Home in Woodstock
Grand 1800s Victorian Gem: Updated/by Downtown
5 bedrooms, 7 beds, 3.5 bathrooms
13–18 Sept
4.9 out of 5 average rating, 100 reviews
Top guest favourite
Guest house in McHenry
"The Apartment" in the heart of downtown McHenry
2 bedrooms, 2 beds, 1 bathroom
14–19 Sept
4.96 out of 5 average rating, 213 reviews
Top guest favourite
Cabin in Woodstock
Cabin on the Prairie
3 bedrooms, 5 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 27 reviews
Guest favourite
Barn in Woodstock
Rustic Barn Retreat with Indoor Pool, Sauna & More
6 bedrooms, 12 beds, 4.5 bathrooms
10–15 Sept
4.73 out of 5 average rating, 15 reviews
Home in Woodstock
Cherry Branch Guest House steps to historic Square
3 bedrooms, 3 beds, 3.5 bathrooms
24–29 Sept
4.67 out of 5 average rating, 3 reviews
Guest favourite
Home in McHenry
Riverfront Entertainment Haven
4 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 16 reviews
Home in Woodstock
The Matador
5 bedrooms, 9 beds, 4.5 bathrooms
27 Oct – 1 Nov
Guest favourite
Home in Crystal Lake
Downtown Vintage Retreat
2 bedrooms, 3 beds, 1 bathroom
5–10 Nov
4.94 out of 5 average rating, 32 reviews