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Search results; Over 1,000 homes in Woodstock

Top guest favourite
Loft in Woodstock
Curated Loft Retreat in The Heart Of Woodstock
1 bedroom, 1 bed, 1 private bathroom
9–14 Aug
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4.96 out of 5 average rating, 227 reviews
Guest favourite
Flat in Woodstock
Cute private apartment 0.6mi from Woodstock Square
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Top guest favourite
Flat in Woodstock
Cute apartment near the Historic Woodstock Square
4.98 out of 5 average rating, 56 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Home in Woodstock
The Tailor House: 2BR w/ Hot Tub near Woodstock Sq
4.95 out of 5 average rating, 275 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
14–19 Aug
Serviced apartment in Woodstock
Historic Apartment on the Woodstock Square
4.86 out of 5 average rating, 304 reviews, 2 bedrooms, 2 beds, 1 bathroom
22–27 Aug
Guest favourite
Home in Woodstock
Finally… A Home Big Enough for Everyone 8 Beds
5.0 out of 5 average rating, 6 reviews, 5 bedrooms, 8 beds, 2 bathrooms
15–20 Aug
Place to stay in Woodstock
Petunia @The Cherry Branch Guest House
1 bedroom, 1 bed, 1.5 bathrooms
23–28 Aug
Home in Woodstock
Woods at Woodstock
New place to stay, 3 bedrooms, 2 beds, 2 bathrooms
24–29 Aug
Guest favourite
Loft in Woodstock
The Lux Loft~Walk to Square/Train Link to Chicago
4.99 out of 5 average rating, 77 reviews, 2 bedrooms, 2 beds, 1 bathroom
3–8 Jan
Top guest favourite
Flat in McHenry
Walk to downtown McHenry. Heart of the Fox River
5.0 out of 5 average rating, 188 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
Guest favourite
Room in Crystal Lake
Beautiful private and cozy room.
4.82 out of 5 average rating, 98 reviews, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
Guest favourite
Home in Crystal Lake
Charming Vintage Cottage Near the Lake
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
25–30 Aug
Bed and breakfast in Woodstock
Old Oak Suite @ Cherry Tree Inn B&B
5.0 out of 5 average rating, 8 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Aug
Guest favourite
Room in Woodstock
New Orleans Room! Mardi Gras House
5.0 out of 5 average rating, 17 reviews, 1 double bed, 1 bathroom
1–6 Jul
Top guest favourite
Room in Woodstock
Hot Tub Spa Suite! Mardi Gras House
5.0 out of 5 average rating, 79 reviews, 1 queen bed, 1 bathroom
1–6 Jul
Top guest favourite
Tiny home in Marengo
Lakeside Tiny House Farm Retreat
4.94 out of 5 average rating, 35 reviews, 1 bedroom, 1 bed, WC
16–21 Aug
Top guest favourite
Cabin in Woodstock
Cabin on the Prairie
5.0 out of 5 average rating, 25 reviews, 3 bedrooms, 5 beds, 1 bathroom
4–9 Sept
Top guest favourite
Home in Round Lake Beach
Round Lake Getaway Retreat
5.0 out of 5 average rating, 206 reviews, 2 bedrooms, 4 beds, 1 bathroom
4–9 Oct
Top guest favourite
Room in East Dundee
2 blocks from restaurants+bars *No cleaning fee!
4.96 out of 5 average rating, 95 reviews, 1 queen bed, 1 bathroom
2–7 Aug