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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

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, (58 reviews)
"Thank you. Would definitely stay again."
United States
Brandon B.
The price is €233
includes taxes & fees
1 Nov - 2 Nov
The Tailor House
A bedroom with a large bed, two bedside tables with lamps, and a tapestry depicting a waterfall.

2. 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 €186
includes taxes & fees
15 Nov - 16 Nov
Sanctuary Woodland Guest House, located next to the conservation area!
A wooden deck with a table and chairs, surrounded by lush greenery and trees.

3. 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 €272
includes taxes & fees
31 Oct - 1 Nov
Spacious 3 Bedroom
A room with a sliding barn-style door, a wooden table, and a double washing machine in the adjacent room.

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 €338
includes taxes & fees
12 Nov - 13 Nov
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 €367
includes taxes & fees
29 Nov - 30 Nov
The Main Event Game House on the Huntley Square!
A kitchen with a view of a lake, wooden cabinets, a dining area with a table and chairs, and a kitchen island.

6. 5-bedroom Lakefront Getaway on Private Wonder Lake – Sleeps 8

5-bedroom Lakefront Getaway on Private Wonder Lake – Sleeps 8
Wonder Lake
9.4 out of 10, Exceptional, (13 reviews)
"Place was really nice and hosts were very friendly and helpful."
United States
Olivia F.
The price is €651
includes taxes & fees
2 Nov - 3 Nov
5-bedroom Lakefront Getaway on Private Wonder Lake – Sleeps 8
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 €421
includes taxes & fees
2 Nov - 3 Nov
King bed Crystal Lake Mchenry Cary Cozy
A two-story house with a swimming pool, outdoor seating, and a stone chimney.

8. 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, (47 reviews)
"This place was amazing. We had a large group and it did not disappoint. The place was clean and well stocked. The host was so accommodating and the communication was great. We would stay here again for sure."
United States
Darlene C.
The price is €1,428
includes taxes & fees
12 Nov - 13 Nov
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
A two-story house with a front porch, a mailbox, and a number '10216' on the door.

9. 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 €972
includes taxes & fees
12 Nov - 13 Nov
1905 Victorian Farmhouse close to Lake Geneva.
A bedroom with a wooden headboard, a bed, a bench, a chair, and a view of the outdoors.

10. 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 €209
includes taxes & fees
2 Nov - 3 Nov
The Little Farm Fontana 5 min from Geneva Lake!
A two-story house with a balcony, a flag, and outdoor seating.

11. 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 €295
includes taxes & fees
1 Nov - 2 Nov
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.

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

✨ Newly Remodeled 3BR Home Sleeps 6 Family Friendly
Elgin
9.4 out of 10, Exceptional, (3 reviews)
"Great place"
United States
Sthendall M.
The price is €306
includes taxes & fees
16 Nov - 17 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.

13. Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (76 reviews)
"We had a great stay! The area was peaceful and felt safe. "
United States
Yoselin V.
The price is €324
includes taxes & fees
31 Oct - 1 Nov
Quaint Bungalow, near Great Lakes Naval Base
A living room with a brown leather sofa, a patterned rug, a framed picture on the wall, a small table with a lamp, and a window with stained glass.

14. 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, (27 reviews)
"Everything was excellent."
United States
Ron P.
The price is €291
includes taxes & fees
31 Oct - 1 Nov
Horse lovers paradise with 2 bedrooms and WiFi, AC in Lake Geneva
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 €214
includes taxes & fees
1 Nov - 2 Nov
The Basecamp 3-bedroom house with AC in charming Walworth
A cozy lodge with a deck, outdoor seating, and a barbecue area.

16. 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)
"Nice property 15-20 min away from downtown lake geneva."
United States
Nate P.
3-bed 2-bath fully remodeled house walking distance to Lake w/ parking for Boat!
A modern kitchen with stainless steel appliances, white cabinets, and a wooden floor.

17. 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, (20 reviews)
"Very nice,clean, very satisfied"
United States
dawn h.
The price is €228
includes taxes & fees
1 Nov - 2 Nov
Cozy 2BR Lake Geneva Home, Fire Pit, Sleeps 6
A porch with wicker furniture and a red door, number 325, overlooking a street with greenery.

18. Newly Renovated |Private Home in the Heart of Downtown Lake Geneva |Dog Friendly |Secluded Back Deck

Newly Renovated |Private Home in the Heart of Downtown Lake Geneva |Dog Friendly |Secluded Back Deck
Lake Geneva
9.8 out of 10, Exceptional, (52 reviews)
"Such a great location and a cute place to stay!!!! That's we're very comfortable and plenty of space for everyone!!!"
United States
Jamee V.
The price is €407
includes taxes & fees
31 Oct - 1 Nov
Newly Renovated |Private Home in the Heart of Downtown Lake Geneva |Dog Friendly |Secluded Back Deck
A dining area with a round wooden table, white chairs, and a hanging light fixture.

19. Chic 3 bedroom Get-a-way in downtown Lake Geneva

Chic 3 bedroom Get-a-way in downtown Lake Geneva
Lake Geneva
9.8 out of 10, Exceptional, (22 reviews)
"Hosts were very responsive to any questions I had, it was clean, very spacious and perfect distance from everything!!"
United States
Sharon R.
The price is €509
includes taxes & fees
1 Nov - 2 Nov
Chic 3 bedroom Get-a-way in downtown Lake Geneva
A modern living room with a dining area, a sofa, a TV, and a fireplace.

20. Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from Chicago

Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from Chicago
Elgin
10.0 out of 10, Exceptional, (25 reviews)
"This was a great house with a beautiful property!"
United States
Malcolm S.
The price is €440
includes taxes & fees
2 Nov - 3 Nov
Pet/Family Friendly Farmhouse: Sleeps 10, Firepit, 1 Hour from Chicago
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
"Beautiful and clean property. Walking short distance to the lake."
Thomas 1-night trip
Posted 3 hours ago
Abbey Resort and Avani Spa

Find out more about Woodstock

Woodstock Holiday Homes information

Number of reviews
503
Accommodation
571 Holiday Homes
Lowest Price
€186
Highest Price
€1,428