Woodstock holiday rentals

From simple studios to luxe lofts, find holiday rentals that are right for you on Airbnb.

Holiday rentals in Woodstock

$133 AUD The "Promised Lands" in Woodstock, IL
34 reviews

This lovely country getaway is located on 5 acres with wooded seclusion in front & open views of horse pastures in back - NO TRAFFIC! Enjoy the privacy & peacefulness that coun... read more
$133 AUD Wonderful Retreat in Woodstock
28 reviews

Welcome! This wonderful private upper apartment is large, clean, and located in the very unique historic town of Woodstock, IL. Groundhog Day was filmed here. Come relax and ... read more
$208 AUD The Lux Loft Woodstock-Train to ORD
17 reviews

Escape the city without a car to this gorgeous timber loft. The train from Chicago stops just three blocks away. Charming Woodstock (of Bill Murray's "Groundhog Day") offers... read more
$47 AUD Cozy Room In Central Crystal Lake
17 reviews

Very nice, clean, single room perfect for a short night or an extended monthly stay. Walk to downtown Crystal Lake where there is shopping, pubs and restaurants or take the Met... read more
$64 AUD Private in-law apt. on the Popular Chain of Lakes!
22 reviews

This is an entire private apt. in a lower level walk-out of my waterfront home on Dutch Creek Bay on the Fox River on the Chain of Lakes. Bring your boat or PWC and park in my s... read more
$20 AUD Unique! TREE HOUSE Camping 6ft off the ground. :)
11 reviews

Custom built Tree house, by me. I secretly wanted this tree fort more than my kids, prob because I grew up in the city. Clean, peaceful and primitive. guests (5-6 total). The... read more

Favourite Woodstock holiday rentals

$174 AUD Hennessey's Hideaway - On the Chain
4 reviews

My place is close to Chain O Lakes, great views, restaurants and dining, family-friendly activities, nightlife. You’ll love my place because of Perfect location close to all the... read more
$32 AUD Jordan Colonial Twin Suite
4 reviews

Our home is located on a quiet cul-de-sac close to Cary-Grove High School, local parks, trails, and ponds. Our entire 1st floor is shared living space with distinct rooms to wor... read more
$168 AUD Vern & Toni's
10 reviews

My place is good for couples, solo adventurers, business travelers, families (with kids). Nature lovers & outdoor enthusiasts will love this place. Plenty of marinas & boat laun... read more
$389 AUD Romantic Lake close to Lake Geneva and Wilmot Ski
10 reviews

My place is on the lake with a private beach, dock, and boat ramp. Pontoon boat rental is available in the Marina. You can bring your watercraft and enjoy tubing, water skiing, ... read more
$93 AUD Clean Furnished Waterfront Stay
9 reviews

Apartment overlooking the Fox River. Walking distance to downtown Algonquin with full kitchen and bathroom. Free wifi & cable TV. I’m always looking forward to hosting great ... read more
$255 AUD The Cabin on Top of Cedar
20 reviews

Rustic cabin an hour from Chicago, Milwaukee or Rockford but feels like it's in the Northwoods. Stay and save at the Cabin on top of Cedar! The Cabin sleeps 10, and has plenty ... read more

More holiday rentals in Woodstock

$161 AUD Cozy Studio w/full kitchen and bath
66 reviews

Cozy studio with full/stocked kitchen & full bath in country/farm setting (no farm animals). Comfortably fits 2/3 and is located in separate building from house. Enjoy outdoor k... read more
$336 AUD Glacier escape - Lake Front House
21 reviews

Directly on the lake 4000 SF house for Family Events. Sleeps comfortably 12 adults. Fits up to 20 people. There are extra futons and queen air mattress. 4 rooms+large open area ... read more
$181 AUD "A" Frame Brandenburg Lake
75 reviews

Getaway to a cozy 1 bedrm w/loft for 2, or 4. Full kitchen 1.5 bath. There is a piano as well. A tranquil home steps from a private lake. Oak and Pine surround you plus a stone ... read more

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