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Search results; Over 1,000 homes in Woodstock

Top guest favourite
Flat in Woodstock
Cute apartment near the Historic Woodstock Square
1 bedroom, 3 beds, 1 private bathroom
28 Sept – 3 Oct
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4.98 out of 5 average rating, 58 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
4.93 out of 5 average rating, 289 reviews
Guest favourite
Home in Woodstock
Finally… A Home Big Enough for Everyone 8 Beds
5 bedrooms, 8 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 10 reviews
Guest favourite
Flat in Woodstock
Historic Apartment on the Woodstock Square
2 bedrooms, 2 beds, 1 bathroom
1–6 Nov
4.86 out of 5 average rating, 311 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
Guest favourite
Flat in Woodstock
Cute private apartment 0.6mi from Woodstock Square
1 bedroom, 1 king bed, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 12 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, 233 reviews
Home in Woodstock
The Matador
5 bedrooms, 9 beds, 4.5 bathrooms
27 Oct – 1 Nov
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
Guest suite in Algonquin
Private Woodland Suite • Fireplace • Near Downtown
1 bedroom, 2 beds, 1 bathroom
5–10 Oct
New place to stay
Home in Woodstock
Cherry Branch Guest House steps to historic Square
3 bedrooms, 3 beds, 3.5 bathrooms
26–31 Oct
4.67 out of 5 average rating, 3 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, 28 reviews
Guest favourite
Home in McHenry
Riverfront Entertainment Haven
4 bedrooms, 7 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Woodstock
Grand 1800s Victorian Gem: Updated/by Downtown
5 bedrooms, 7 beds, 3.5 bathrooms
14–19 Sept
4.9 out of 5 average rating, 100 reviews
Bed and breakfast in Woodstock
Old Oak Suite @ Cherry Tree Inn B&B
1 bedroom, 2 queen beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 9 reviews
Guest favourite
Home in Crystal Lake
Hot tub. Heated Pool. In town location.
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 46 reviews
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, 28 reviews
Guest favourite
Home in Lake Geneva
Lake Geneva Modern Farmhouse/Spacious!
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
4.7 out of 5 average rating, 10 reviews
Top 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, 33 reviews