A park with a bench, trees with autumn leaves, a grassy area, and a building in the background.

Holiday Homes in Woodstock

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Woodstock holiday homes

Exterior

1. The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (56 reviews)
"Amazing stay. So close to everything!"
United States
Brittany H.
The price is AU$396
includes taxes & fees
24 Aug - 25 Aug
The Tailor House
Private kitchen

2. Charming 2-bedroom house with WiFi, AC in fabulous Woodstock

Charming 2-bedroom house with WiFi, AC in fabulous Woodstock
Woodstock
8.0 out of 10, Very good, (1 review)
"I was very surprised that the property was by itself on a 2 lane road. We initially drove past it because there was nothing on the side of the road with the address. It was next to an odd and ugly"building." It was less than 10 minutes frim town, which was good. The house was clean, but REEKED of mildew. We bought stuff to help with the smell (which we left for future guests), but it was still bad. There was no toaster or microwave, and there was someone elase's Culver's in the freezer....
United States
Anonymous traveller
The price is AU$527
includes taxes & fees
27 Aug - 28 Aug
Charming 2-bedroom house with WiFi, AC in fabulous Woodstock
2 bedrooms, iron/ironing board, free WiFi, bed sheets

3. Sanctuary Woodland Guest House, located next to the conservation area!

Sanctuary Woodland Guest House, located next to the conservation area!
Harvard
10.0 out of 10, Exceptional, (26 reviews)
"The property is so cute and it was the perfect, quiet place to stay! The owner was super friendly as well!"
United States
Jamie S.
The price is AU$274
includes taxes & fees
20 Aug - 21 Aug
Sanctuary Woodland Guest House, located next to the conservation area!
House

4. King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is AU$623
includes taxes & fees
23 Aug - 24 Aug
King bed Crystal Lake Mchenry Cary Cozy
Interior

5. Terrific 3-bedroom family-friendly house close to everything in charming McHenry

Terrific 3-bedroom family-friendly house close to everything in charming McHenry
McHenry
8.6 out of 10, Excellent, (10 reviews)
"It was very conveniently located"
United States
Rita L.
The price is AU$416
includes taxes & fees
24 Aug - 25 Aug
Terrific 3-bedroom family-friendly house close to everything in charming McHenry
Outdoor dining

6. Spacious 3 Bedroom

Spacious 3 Bedroom
Cary
8.0 out of 10, Very good, (1 review)
"Conveniently located near restaurants and downtown. Apartment was clean. Nicely decorated. Cute coffee station. Big table in dining area."
United States
Kim B.
The price is AU$493
includes taxes & fees
23 Aug - 24 Aug
Spacious 3 Bedroom
Marina

7. This is a VACATION spot with a million dollar view!

This is a VACATION spot with a million dollar view!
fox lake
9.8 out of 10, Exceptional, (28 reviews)
"Great location!! Beautiful place!!!"
United States
Jason C.
The price is AU$673
includes taxes & fees
1 Sept - 2 Sept
This is a VACATION spot with a million dollar view!
Exterior

8. The Main Event Game House on the Huntley Square!

The Main Event Game House on the Huntley Square!
Huntley
10.0 out of 10, Exceptional, (21 reviews)
"Our stay was very comfortable and the game room was great for our big family. The kids didn't want to leave and always ask about going back."
United States
BENJAMIN B.
The price is AU$415
includes taxes & fees
30 Aug - 31 Aug
The Main Event Game House on the Huntley Square!
Marina

9. The Little Farm Fontana 5 min from Geneva Lake!

The Little Farm Fontana 5 min from Geneva Lake!
Fontana-on-Geneva Lake
10.0 out of 10, Exceptional, (1 review)
"Cute little place in a convenient location for a fair price."
United States
Linda C.
The price is AU$371
includes taxes & fees
20 Aug - 21 Aug
The Little Farm Fontana 5 min from Geneva Lake!
Exterior detail

10. Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (74 reviews)
"Fantastic location. Very clean. Great/quick communication with host. Definitely recommend!"
United States
Jaclyn Z.
The price is AU$487
includes taxes & fees
8 Sept - 9 Sept
Quaint Bungalow, near Great Lakes Naval Base
Coffee/tea maker, fridge, microwave, oven

11. Cozy Home In Lake Geneva WI Area

Cozy Home In Lake Geneva WI Area
Lake Geneva
9.0 out of 10, Wonderful, (17 reviews)
"Super clean,quiet house! Close to water for us to launch our boat. We would definitely stay again, Thank You"
United States
kelly b.
The price is AU$351
includes taxes & fees
8 Sept - 9 Sept
Cozy Home In Lake Geneva WI Area
Exterior

12. Horse lovers paradise with 2 bedrooms and WiFi, AC in Lake Geneva

Horse lovers paradise with 2 bedrooms and WiFi, AC in Lake Geneva
Lake Geneva
10.0 out of 10, Exceptional, (24 reviews)
"The setting is perfect, and the apartment is spacious and comfortable."
United States
Marsha S.
The price is AU$454
includes taxes & fees
20 Aug - 21 Aug
Horse lovers paradise with 2 bedrooms and WiFi, AC in Lake Geneva
Exterior

13. 1905 Victorian Farmhouse close to Lake Geneva.

1905 Victorian Farmhouse close to Lake Geneva.
Hebron
10.0 out of 10, Exceptional, (32 reviews)
"Repeat guest! We will be looking for this property again if we stay in the same area."
United States
Shari
The price is AU$1,471
includes taxes & fees
23 Aug - 24 Aug
1905 Victorian Farmhouse close to Lake Geneva.
Interior

14. 3-bed 2-bath fully remodeled house walking distance to Lake w/ parking for Boat!

3-bed 2-bath fully remodeled house walking distance to Lake w/ parking for Boat!
Lake Geneva
10.0 out of 10, Exceptional, (25 reviews)
"3 bedrooms was great. Very clean. Enjoyed our stay."
United States
Sharon K.
The price is AU$599
includes taxes & fees
30 Aug - 31 Aug
3-bed 2-bath fully remodeled house walking distance to Lake w/ parking for Boat!
Outdoor dining

15. Hot Tub Retreats

Hot Tub Retreats
Lake Villa
10.0 out of 10, Exceptional, (1 review)
"Very clean and cozy I loved my stay"
United States
Rosilynn B.
The price is AU$469
includes taxes & fees
1 Sept - 2 Sept
Hot Tub Retreats
Interior

16. Riverfront rental

Riverfront rental
South Elgin
10.0 out of 10, Exceptional, (48 reviews)
"Cozy home, perfect for a relaxting time away "
United States
Phoenicia
The price is AU$381
includes taxes & fees
20 Aug - 21 Aug
Riverfront rental
TV

17. Salem Vacation Home w/ Dock: Steps to Paddock Lake

Salem Vacation Home w/ Dock: Steps to Paddock Lake
Salem
9.2 out of 10, Wonderful, (11 reviews)
"Was a nice little get away location. "
United States
Shanna D.
The price is AU$1,265
includes taxes & fees
20 Aug - 21 Aug
Salem Vacation Home w/ Dock: Steps to Paddock Lake
Interior

18. Quick Trip Getaway |Fun Southwestern Vibe |Enclosed Porch |Walkable to Downtown Lake Geneva |Parking

Quick Trip Getaway |Fun Southwestern Vibe |Enclosed Porch |Walkable to Downtown Lake Geneva |Parking
Lake Geneva
9.8 out of 10, Exceptional, (29 reviews)
"The location was easy to find and perfect walking distance to downtown. "
United States
Griffin Y.
The price is AU$605
includes taxes & fees
31 Aug - 1 Sept
Quick Trip Getaway |Fun Southwestern Vibe |Enclosed Porch |Walkable to Downtown Lake Geneva |Parking
Coffee/tea maker, fridge, microwave, oven

19. Modern Waters- Bright and Central- Walk to Downtown

Modern Waters- Bright and Central- Walk to Downtown
Lake Geneva
10.0 out of 10, Exceptional, (8 reviews)
"Great location and easy parking. The unit was great-- clean and plenty of room. "
United States
Leigh Ann M.
The price is AU$909
includes taxes & fees
25 Aug - 26 Aug
Modern Waters- Bright and Central- Walk to Downtown
Interior

20. The Basecamp 3-bedroom house with AC in charming Walworth

The Basecamp 3-bedroom house with AC in charming Walworth
Walworth
7.6 out of 10, Good, (7 reviews)
"The host allowed early check in and late check out, which we were very grateful for. However, he forgot about our late check out, so cleaners showed up while we were getting ready for a wedding and pressured us to leave. That felt stressful. The house itself is a cool old building. There's tons of potential. But the dining room and living room aren't functional for a house that sleeps 8. There's no dining table. And the living room has only a single loveseat and coffee table. The beds are...
United States
Alyssa W.
The price is AU$418
includes taxes & fees
1 Sept - 2 Sept
The Basecamp 3-bedroom house with AC in charming Walworth
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Woodstock Hotel Reviews

Abbey Resort and Avani Spa

Abbey Resort and Avani Spa

10/10 Excellent
"Had a great time at the Abbey"
Dawn 3-night trip
Posted 3 hours ago
Abbey Resort and Avani Spa

Find out more about Woodstock

Woodstock Holiday Homes information

Number of reviews
Accommodation
572 Holiday Homes
Lowest Price
AU$623
Highest Price
AU$2,916