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

Woodstock Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Woodstock vacation rentals

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 ￥20,246
￥39,895 total
includes taxes & fees
Oct 27 - Oct 28
The Tailor House
A red house with a porch, a wooden staircase, and a flag.

2. Lovely 1-bedroom apartment with AC in charming Woodstock

Lovely 1-bedroom apartment with AC in charming Woodstock
Woodstock
8.0 out of 10, Very good, (3 reviews)
"Everything was great! The property is close to everything and was easy to access. The only drawback was the air conditioning in the bedroom was very loud. Other than that no problems."
United States
Beth B.
The price is ￥23,726
￥28,498 total
includes taxes & fees
Oct 25 - Oct 26
Lovely 1-bedroom apartment with AC in charming Woodstock
Living area

3. Wonder Lake Elegance: Serene 2BR Townhome Retreat

Wonder Lake Elegance: Serene 2BR Townhome Retreat
Wonder Lake
9.6 out of 10, Exceptional, (4 reviews)
"Very clean and comfortable. Quiet neighborhood."
United States
Ken S.
The price is ￥29,303
￥57,875 total
includes taxes & fees
Oct 26 - Oct 27
Wonder Lake Elegance: Serene 2BR Townhome Retreat
A bedroom with a large bed, two bedside tables with lamps, and a tapestry depicting a waterfall.

4. 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 ￥21,986
￥32,019 total
includes taxes & fees
Nov 19 - Nov 20
Sanctuary Woodland Guest House, located next to the conservation area!
A kitchen with a dark wooden table, white cabinets, and a sliding barn door.

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, (13 reviews)
"Nearby lots of restaurants and business as well as a nice park."
United States
Cj D.
The price is ￥33,058
￥55,820 total
includes taxes & fees
Oct 24 - Oct 25
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.

6. 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 ￥30,052
￥52,969 total
includes taxes & fees
Nov 4 - Nov 5
The Main Event Game House on the Huntley Square!
A two-story house with a swimming pool, outdoor seating, and a stone chimney.

7. 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 ￥88,101
￥231,199 total
includes taxes & fees
Nov 3 - Nov 4
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.

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 ￥94,902
￥170,143 total
includes taxes & fees
Oct 25 - Oct 26
1905 Victorian Farmhouse close to Lake Geneva.
An outdoor patio with stone flooring, a wooden table and chairs, a stone wall, and a fire pit.

9. Little Fox Cottage - A Cozy Riverview Getaway

Little Fox Cottage - A Cozy Riverview Getaway
Fox River Grove
9.8 out of 10, Exceptional, (20 reviews)
"Host and amenities were great!"
United States
Jeff P.
The price is ￥19,218
￥31,600 total
includes taxes & fees
Oct 26 - Oct 27
Little Fox Cottage - A Cozy Riverview Getaway
A spacious living area with a grey sofa, wooden flooring, and a kitchen area with a bar.

10. Richmond No. 267 Boutique Loft Apartment

Richmond No. 267 Boutique Loft Apartment
Richmond
10.0 out of 10, Exceptional, (17 reviews)
"Very spacious, clean & great location!"
United States
Ernesta T.
The price is ￥27,284
￥46,552 total
includes taxes & fees
Oct 26 - Oct 27
Richmond No. 267 Boutique Loft Apartment
An indoor water park with a 'Welcome' sign, slides, and a hot tub area.

11. Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark
3.5 star property
Lake Geneva
8.6 out of 10, Excellent, (3,491 reviews)
"Great place for families looking for a quaint stay. My kids absolutely loved it. We will return"
United States
Kimberly L
The price is ￥17,041
￥25,178 total
includes taxes & fees
Oct 29 - Oct 30
Timber Ridge Lodge and Waterpark
An indoor swimming pool with wooden walls and ceiling, surrounded by lounge chairs and potted plants.

12. Mill Creek Hotel

Mill Creek Hotel
2.5 star property
Lake Geneva
9.2 out of 10, Wonderful, (1,273 reviews)
"clean, comfortable and great location"
United States
Marshall
The price is ￥29,420
￥33,392 total
includes taxes & fees
Nov 1 - Nov 2
Mill Creek Hotel
A bedroom with a brick wall, a bed, a desk, and a window with a view.

13. 124 Lofts #4 - Downtown Dundee - Walk to Dining

124 Lofts #4 - Downtown Dundee - Walk to Dining
West Dundee
9.8 out of 10, Exceptional, (20 reviews)
"Awesome loft. Perfect for an overnight stay. Convenient parking and lots of restaurants to choose from."
United States
Shannon
The price is ￥30,527
￥38,382 total
includes taxes & fees
Oct 26 - Oct 27
124 Lofts #4 - Downtown Dundee - Walk to Dining
A wicker tray with a pitcher and glasses on a wooden table on a porch.

14. Kildahl House - Boutique Farmhouse Suite #1

Kildahl House - Boutique Farmhouse Suite #1
West Dundee
9.8 out of 10, Exceptional, (19 reviews)
"We had a wonderful stay at the Kildahl House! It is clean, cozy, charming. The location is perfect and accessible to to the river and downtown. I loved the connections Andy and Suzanne have made with local businesses to make your stay even more enjoyable!"
United States
Elise L.
The price is ￥33,058
￥41,885 total
includes taxes & fees
Oct 26 - Oct 27
Kildahl House - Boutique Farmhouse Suite #1
A wicker tray with a pitcher and glasses on a wooden table on a porch.

15. Kildahl House - Boutique Farmhouse Suite #2

Kildahl House - Boutique Farmhouse Suite #2
West Dundee
10.0 out of 10, Exceptional, (19 reviews)
"I would stay here again in a heartbeat!"
United States
Rebecca R.
The price is ￥33,058
￥41,885 total
includes taxes & fees
Oct 29 - Oct 30
Kildahl House - Boutique Farmhouse Suite #2
A hotel room with a bed, a desk, a lamp, a TV, and a framed artwork.

16. 124 Lofts #1 - Downtown Dundee - Walk to Dining

124 Lofts #1 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (17 reviews)
"Fantastic hosts, fantastic spot!"
United States
Haggard A.
The price is ￥28,016
￥35,572 total
includes taxes & fees
Nov 15 - Nov 16
124 Lofts #1 - Downtown Dundee - Walk to Dining
A house by a lake with docked boats and a flag.

17. 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 ￥71,177
￥105,438 total
includes taxes & fees
Oct 23 - Oct 24
This is a VACATION spot with a million dollar view!
A modern living room with a fireplace, a television mounted on the wall, and a balcony with a view of the outdoors.

18. Modern Lake Geneva Condo with Views

Modern Lake Geneva Condo with Views
Lake Geneva
8.8 out of 10, Excellent, (12 reviews)
"Location was perfect…walk to restaurants and kayak rental on Lake Como. Condo was very clean and met all our needs. Enjoyed the pool very much. Great stay!"
United States
Mary L.
The price is ￥53,936
￥109,781 total
includes taxes & fees
Oct 27 - Oct 28
Modern Lake Geneva Condo with Views
A swimming pool with a 5ft depth marker, surrounded by lounge chairs and a stone wall.

19. LG 1+1 Condo on Lakeshore - pool - walk to Lake

LG 1+1 Condo on Lakeshore - pool - walk to Lake
Lake Geneva
The price is ￥16,956
￥70,614 total
includes taxes & fees
Nov 17 - Nov 18
LG 1+1 Condo on Lakeshore - pool - walk to Lake
A house with a blue door, a small porch, and a potted plant.

20. Suite 3. Breakfast at Tiffany's Suite. Downtown Williams Bay. Steps to Beach.

Suite 3. Breakfast at Tiffany's Suite. Downtown Williams Bay. Steps to Beach.
Williams Bay
10.0 out of 10, Exceptional, (3 reviews)
"Very clean, fun and new decor, well-stocked kitchen, great location, comfortable bed"
United States
Kathy C.
The price is ￥30,577
￥38,683 total
includes taxes & fees
Oct 25 - Oct 26
Suite 3. Breakfast at Tiffany's Suite. Downtown Williams Bay. Steps to Beach.
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

Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

8/10 Good
"The proximity to downtown and being walking distance to restaurants and shops was wonderful. The hotel was clean and staff was helpful. There were somethings that felt dated throughout the hotel. There also seemed to always an odd amount of people mulling around in the lobby, but while we were there there were several events happening in their event spaces. The room itself was clean and comfortable and had a wonderful view of the lake. The only disappointing space was the bathroom which looked to have been hastily renovated and poorly executed. Overall our stay was wonderful and we had a great time in Lake Geneva"
Zachary 2-night trip
Posted 1 hour ago
Harbor Shores on Lake Geneva

Find out more about Woodstock

Search for holiday rentals in Woodstock on Expedia! You can easily find your home rentals, villas, holiday apartments in Woodstock using one of the methods below:

  • View our selection of featured holiday rentals in Woodstock
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Look no further and take a look at our great range of rental properties in Woodstock!

Frequently asked questions

Can I find vacation rentals in Woodstock?

Yes, we offer vacation rentals in Woodstock close to McHenry County Fairgrounds, or you can choose a more remote option if you're looking for extra privacy while you relax. Woodstock is known for its shopping and jazz scene. Make sure you have time to check out the golf courses while you're in the area.

What are some of the best vacation home rentals that Woodstock has to offer?

Luxury Lake Geneva cottage w/ sauna + hot tub + geodesic dome on 2-acres: Visitors like this Woodstock vacation home rental. It is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Woodstock?

Choose from 8 Expedia vacation rentals in Woodstock for a memorable vacation.

What can I see and do in Woodstock?

Cultural attractions include Woodstock Opera House, whereas Emricson Park is a spot to enjoy nature. While here, Woodstock Square and McHenry County Fairgrounds are other places worth a visit.

What are vacation rentals like in Woodstock?

Vacation rentals are privately owned accommodations you can reserve for several days or more in Woodstock. Vacation rentals feature extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.