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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Woodstock holiday homes

A white house with a porch and a chimney, surrounded by a grassy area and a brick path.

1. The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (57 reviews)
"Thank you. Would definitely stay again."
United States
Brandon B.
The price is AU$363
includes taxes & fees
6 Oct - 7 Oct
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$529
includes taxes & fees
6 Oct - 7 Oct
Charming 2-bedroom house with WiFi, AC in fabulous Woodstock
A bedroom with a large bed, two bedside tables with lamps, and a tapestry depicting a waterfall.

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, (28 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$288
includes taxes & fees
25 Oct - 26 Oct
Sanctuary Woodland Guest House, located next to the conservation area!
A kitchen with a dark wooden table, white cabinets, and a sliding barn door.

4. 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, (13 reviews)
"Nearby lots of restaurants and business as well as a nice park."
United States
Cj D.
The price is AU$423
includes taxes & fees
6 Oct - 7 Oct
Terrific 3-bedroom family-friendly house close to everything in charming McHenry
A two-story house with a front porch, a stone exterior on the right side, and a green door.

5. 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$369
includes taxes & fees
6 Oct - 7 Oct
The Main Event Game House on the Huntley Square!
A wooden deck with a table and chairs, surrounded by lush greenery and trees.

6. Spacious 3 Bedroom

Spacious 3 Bedroom
Cary
9.4 out of 10, Exceptional, (3 reviews)
"Nice quiet spot to rest a Travelers head"
United States
Dan K.
The price is AU$433
includes taxes & fees
6 Oct - 7 Oct
Spacious 3 Bedroom
A modern kitchen with white cabinets, stainless steel appliances, a large window, and a bar stool.

7. King bed Crystal Lake Mchenry Cary Cozy

King bed Crystal Lake Mchenry Cary Cozy
2.0 star property
Cary
The price is AU$688
includes taxes & fees
7 Oct - 8 Oct
King bed Crystal Lake Mchenry Cary Cozy
A two-story house with a front porch, a mailbox, and a number '10216' on the door.

8. 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$1,273
includes taxes & fees
19 Oct - 20 Oct
1905 Victorian Farmhouse close to Lake Geneva.
A two-story house with a swimming pool, outdoor seating, and a stone chimney.

9. HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
McHenry
9.2 out of 10, Wonderful, (46 reviews)
"We stayed with our wedding bridal party here, and this massive and beautiful house was the perfect location to spend the weekend with all of our best friends! The house is obviously gorgeous, and the pool, hot tub, fire pit and pool table added an extra tier of fun. We hosted our rehearsal dinner on the back lawn and rented tables and chairs through the property, which was incredibly convenient.The property managers were communicative and very helpful throughout the process. I highly...
United States
Brittany B.
The price is AU$2,207
includes taxes & fees
6 Oct - 7 Oct
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
A lakeside deck with chairs and a table, a wooden dock extending into the water, and a covered area in the background.

10. Waterfront - Private Dock - Two Suites

Waterfront - Private Dock - Two Suites
Algonquin
The price is AU$861
includes taxes & fees
2 Nov - 3 Nov
Waterfront - Private Dock - Two Suites
An aerial view of a marina with multiple docks and boats, a sandy beach, and surrounding greenery.

11. 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$330
includes taxes & fees
6 Oct - 7 Oct
The Little Farm Fontana 5 min from Geneva Lake!
A house by a lake with docked boats and a flag.

12. 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, (34 reviews)
"Great location!! Beautiful place!!!"
United States
Jason C.
The price is AU$960
includes taxes & fees
9 Oct - 10 Oct
This is a VACATION spot with a million dollar view!
A modern kitchen with grey cabinets, a stainless steel refrigerator, a built-in oven, and a microwave.

13. ✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly

✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
Elgin
9.0 out of 10, Wonderful, (2 reviews)
"Great place"
United States
Sthendall M.
The price is AU$482
includes taxes & fees
2 Nov - 3 Nov
✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
A living room with a dark brown leather sofa, a glass coffee table, a black bean bag, a patterned rug, and a staircase leading to a dining area with wooden chairs.

14. 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, (9 reviews)
"Nice cozy place to stay. Bed was comfortable. Close by everything. Easy check in and out process."
United States
Andrea M.
The price is AU$436
includes taxes & fees
4 Nov - 5 Nov
The Basecamp 3-bedroom house with AC in charming Walworth
Lower level outdoor seating area (electric grill only)

15. Downtown Lake Geneva Hideaway Walk to Lake Music Dining Balcony Sleeps 16

Downtown Lake Geneva Hideaway Walk to Lake Music Dining Balcony Sleeps 16
Lake Geneva
9.8 out of 10, Exceptional, (25 reviews)
"This house and location were the perfect spot to host a bachelorette party! It had plenty of space and was decorated beautifully. We enjoyed having the upper and lower parts of the house to have space for everyone to get ready, play games and hang out together. The backyard was the perfect spot to lounge as well. Downtown, the beach, and most places you would want to go are all within a short walking distance from this great home. Would highly recommend!"
United States
Holly K.
The price is AU$1,008
includes taxes & fees
7 Oct - 8 Oct
Downtown Lake Geneva Hideaway Walk to Lake Music Dining Balcony Sleeps 16
A modern kitchen with stainless steel appliances, white cabinets, and a wooden floor.

16. Cozy 2BR Lake Geneva Home, Fire Pit, Sleeps 6

Cozy 2BR Lake Geneva Home, Fire Pit, Sleeps 6
Lake Geneva
9.0 out of 10, Wonderful, (19 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$359
includes taxes & fees
19 Oct - 20 Oct
Cozy 2BR Lake Geneva Home, Fire Pit, Sleeps 6
A two-story house with a covered outdoor seating area and a fire pit.

17. Oak Cabin near Lake Geneva | Walk to Lake Como, Fire Pit, Coffee Bar

Oak Cabin near Lake Geneva | Walk to Lake Como, Fire Pit, Coffee Bar
Lake Geneva
10.0 out of 10, Exceptional, (2 reviews)
"Perfect location by Lake Como (literally across the street). Nice to be close to a bar/restaurant across the street also (even though it was packed Friday night, you don't hear the noise). Cabin is so adorable! Sad we didn't have time to use the nice fire pit."
United States
Mary B.
The price is AU$435
includes taxes & fees
9 Oct - 10 Oct
Oak Cabin near Lake Geneva | Walk to Lake Como, Fire Pit, Coffee Bar
A two-story house with a stone chimney, a front porch with steps, and a flag.

18. Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (75 reviews)
"Fantastic location. Very clean. Great/quick communication with host. Definitely recommend!"
United States
Jaclyn Z.
The price is AU$501
includes taxes & fees
13 Oct - 14 Oct
Quaint Bungalow, near Great Lakes Naval Base
A traditional building with a symmetrical facade, large windows, and a central tower.

19. 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, (26 reviews)
"Loved the property, it was beautiful and peaceful. Caitlin was super nice and responsive. Would defiantly stay here again."
United States
Kristen M.
The price is AU$466
includes taxes & fees
7 Oct - 8 Oct
Horse lovers paradise with 2 bedrooms and WiFi, AC in Lake Geneva
A living room with a sofa, armchair, coffee table, and decorative items.

20. White House on Wisconsin-Carriage House |Renovated Colonial Revival |Steps to Main St |Parking for 2

White House on Wisconsin-Carriage House |Renovated Colonial Revival |Steps to Main St |Parking for 2
Lake Geneva
9.8 out of 10, Exceptional, (24 reviews)
"The property was very good. My wife and I went for a weekend getaway and it was perfect for us. The location was great and the amenities were just right."
United States
Deepen D.
White House on Wisconsin-Carriage House |Renovated Colonial Revival |Steps to Main St |Parking for 2
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

Bella Vista Suites

Bella Vista Suites

8/10 Good
"It was very nice!! Love the suites but there was a wedding downstairs that was very loud and we couldn’t sleep. It was going on till 2am which we thought was very late for the hotel guests."
Susan 2-night trip
Posted 1 hour ago
Bella Vista Suites

Find out more about Woodstock

Woodstock Holiday Homes information

Number of reviews
287
Accommodation
571 Holiday Homes
Lowest Price
AU$288
Highest Price
AU$2,207