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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 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 NZ$446
includes taxes & fees
12 Oct - 13 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 NZ$658
includes taxes & fees
12 Oct - 13 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 NZ$354
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 NZ$522
includes taxes & fees
15 Oct - 16 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 NZ$445
includes taxes & fees
19 Oct - 20 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 NZ$540
includes taxes & fees
12 Oct - 13 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 NZ$844
includes taxes & fees
21 Oct - 22 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 NZ$1,574
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 NZ$3,051
includes taxes & fees
14 Oct - 15 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 NZ$1,027
includes taxes & fees
3 Nov - 4 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 NZ$418
includes taxes & fees
11 Oct - 12 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 NZ$1,146
includes taxes & fees
12 Oct - 13 Oct
This is a VACATION spot with a million dollar view!
A spacious living area with a large island, modern furniture, and a fireplace.

13. 4Bed 3.5Ba Cozy New Construction! Close to Lake Geneva and Lake Elizabeth!

4Bed 3.5Ba Cozy New Construction! Close to Lake Geneva and Lake Elizabeth!
Twin Lakes
10.0 out of 10, Exceptional, (49 reviews)
"Second time at the home - was clean and comfortable."
United States
Leshonda
The price is NZ$802
includes taxes & fees
12 Oct - 13 Oct
4Bed 3.5Ba Cozy New Construction! Close to Lake Geneva and Lake Elizabeth!
A wooden dining table with a 'Welcome to the Lake' sign above it.

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, (31 reviews)
"Had an absolutely amazing time. "
United States
Jennifer P.
The price is NZ$782
includes taxes & fees
11 Oct - 12 Oct
3-bed 2-bath fully remodeled house walking distance to Lake w/ parking for Boat!
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.

15. 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 NZ$510
includes taxes & fees
20 Oct - 21 Oct
The Basecamp 3-bedroom house with AC in charming Walworth
A modern kitchen with grey cabinets, a stainless steel refrigerator, a built-in oven, and a microwave.

16. ✨ 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 NZ$590
includes taxes & fees
2 Nov - 3 Nov
✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
A two-story house with a stone chimney, a front porch with steps, and a flag.

17. 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 NZ$628
includes taxes & fees
11 Oct - 12 Oct
Quaint Bungalow, near Great Lakes Naval Base
A traditional building with a symmetrical facade, large windows, and a central tower.

18. 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 NZ$575
includes taxes & fees
11 Oct - 12 Oct
Horse lovers paradise with 2 bedrooms and WiFi, AC in Lake Geneva
A grassy outdoor area with a fire pit and two chairs.

19. 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 NZ$444
includes taxes & fees
25 Oct - 26 Oct
Cozy 2BR Lake Geneva Home, Fire Pit, Sleeps 6
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

Lake Lawn Resort

Lake Lawn Resort

10/10 Excellent
"Very clean room, attentive staff and beautiful property. We really enjoyed our stay and can't wait to come back for another relaxing weekend away."
Kaeley 1-night trip
Posted 7 hours ago
Lake Lawn Resort

Find out more about Woodstock

Woodstock Holiday Homes information

Number of reviews
365
Accommodation
585 Holiday Homes
Lowest Price
NZ$354
Highest Price
NZ$3,051