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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Our top choices for Woodstock vacation rentals

1. The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (58 reviews)
"Amazing stay. So close to everything!"
United States
Brittany H.
The price is CA $179
CA $340 total
includes taxes & fees
Nov 8 - Nov 9
The Tailor House

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

Lovely 1-bedroom apartment with AC in charming Woodstock
Woodstock
8.6 out of 10, Excellent, (4 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 CA $210
CA $232 total
includes taxes & fees
Nov 9 - Nov 10
Lovely 1-bedroom apartment with AC in charming Woodstock

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 CA $260
CA $489 total
includes taxes & fees
Nov 8 - Nov 9
Wonder Lake Elegance: Serene 2BR Townhome Retreat

4. 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 CA $279
CA $725 total
includes taxes & fees
Nov 8 - Nov 9
5-bedroom Lakefront Getaway on Private Wonder Lake – Sleeps 8

5. 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)
"Great place"
United States
Christopher W.
The price is CA $189
CA $254 total
includes taxes & fees
Nov 30 - Dec 1
Sanctuary Woodland Guest House, located next to the conservation area!

6. 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 CA $293
CA $472 total
includes taxes & fees
Nov 8 - Nov 9
Terrific 3-bedroom family-friendly house close to everything in charming McHenry

7. 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 CA $174
CA $346 total
includes taxes & fees
Nov 8 - Nov 9
The Main Event Game House on the Huntley Square!

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 CA $592
CA $1,820 total
includes taxes & fees
Nov 9 - Nov 10
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

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 CA $170
CA $270 total
includes taxes & fees
Nov 16 - Nov 17
Little Fox Cottage - A Cozy Riverview Getaway

10. 1905 Victorian close to Lake Geneva. Decorated for the Holidays!

1905 Victorian close to Lake Geneva. Decorated for the Holidays!
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 CA $757
CA $1,242 total
includes taxes & fees
Nov 8 - Nov 9
1905 Victorian close to Lake Geneva. Decorated for the Holidays!

11. Richmond No. 267 Boutique Loft Apartment

Richmond No. 267 Boutique Loft Apartment
Richmond
10.0 out of 10, Exceptional, (18 reviews)
"Very spacious, clean & great location!"
United States
Ernesta T.
The price is CA $242
CA $374 total
includes taxes & fees
Nov 8 - Nov 9
Richmond No. 267 Boutique Loft Apartment

12. Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark
3.5 star property
Lake Geneva
8.6 out of 10, Excellent, (3,523 reviews)
"Great hotel amazing staff and amazing waterpark"
United States
Lindsey
The price is CA $164
CA $237 total
includes taxes & fees
Nov 11 - Nov 12
Timber Ridge Lodge and Waterpark

13. Mill Creek Hotel

Mill Creek Hotel
2.5 star property
Lake Geneva
9.2 out of 10, Wonderful, (1,275 reviews)
"clean, comfortable and great location"
United States
Marshall
The price is CA $261
CA $296 total
includes taxes & fees
Nov 9 - Nov 10
Mill Creek Hotel

14. 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 CA $245
CA $440 total
includes taxes & fees
Nov 11 - Nov 12
This is a VACATION spot with a million dollar view!

15. Lake Geneva, Fireplace, Pool, Wifi, King Bed

Lake Geneva, Fireplace, Pool, Wifi, King Bed
Lake Geneva
10.0 out of 10, Exceptional, (46 reviews)
"Beautiful area with great shops and food."
United States
SUZY R.
The price is CA $129
CA $353 total
includes taxes & fees
Nov 8 - Nov 9
Lake Geneva, Fireplace, Pool, Wifi, King Bed

16. 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)
"Wonderful loft, highly recommend!"
United States
Bret V.
The price is CA $276
CA $323 total
includes taxes & fees
Nov 9 - Nov 10
124 Lofts #4 - Downtown Dundee - Walk to Dining

17. Broad St Earth Suite |Amazing Location in the Heart of Town |Parking Available |King & Queen Bedroom

Broad St Earth Suite |Amazing Location in the Heart of Town |Parking Available |King & Queen Bedroom
Lake Geneva
9.2 out of 10, Wonderful, (30 reviews)
"Loved the couches! Quick walk to wonderful restaurants and lake."
United States
Denise A.
The price is CA $110
CA $410 total
includes taxes & fees
Nov 9 - Nov 10
Broad St Earth Suite |Amazing Location in the Heart of Town |Parking Available |King & Queen Bedroom

18. Blue Beach Cottage - 5 Minute Walk to Private Beach!

Blue Beach Cottage - 5 Minute Walk to Private Beach!
Delavan
9.8 out of 10, Exceptional, (27 reviews)
"Very nice home with all the amenities needed!"
United States
Jennifer V.
The price is CA $150
CA $581 total
includes taxes & fees
Nov 8 - Nov 9
Blue Beach Cottage - 5 Minute Walk to Private Beach!

19. Modern Lake Geneva Condo With Views

Modern Lake Geneva Condo With Views
3.5 star property
Lake Geneva
The price is CA $200
CA $1,104 total
includes taxes & fees
Dec 1 - Dec 2
Modern Lake Geneva Condo With Views

20. Hidden Gem with Pool View!

Hidden Gem with Pool View!
Lake Geneva
10.0 out of 10, Exceptional, (45 reviews)
"Everything was great Love the room and the area"
United States
Thomas P.
The price is CA $168
CA $356 total
includes taxes & fees
Nov 8 - Nov 9
Hidden Gem with Pool View!
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

Find out more about Woodstock

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Woodstock. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.