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

Woodstock Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Woodstock holiday rentals

A hot tub in a backyard with a wooden fence, a table, and chairs.

1. The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (60 reviews)
"Amazing stay. So close to everything!"
United States
Brittany H.
The price is AU$351
includes taxes & fees
17 Nov - 18 Nov
The Tailor House
A wooden deck with a red grill, a chair, and a house in the background.

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 AU$253
includes taxes & fees
18 Nov - 19 Nov
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 AU$505
includes taxes & fees
17 Nov - 18 Nov
Wonder Lake Elegance: Serene 2BR Townhome Retreat
A fenced outdoor area with trees and a building in the background.

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)
"Great place"
United States
Christopher W.
The price is AU$277
includes taxes & fees
16 Nov - 17 Nov
Sanctuary Woodland Guest House, located next to the conservation area!
A lakeside patio with a table and chairs, a swing set, and an American flag.

5. 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 AU$738
includes taxes & fees
17 Nov - 18 Nov
5-bedroom Lakefront Getaway on Private Wonder Lake – Sleeps 8
A kitchen with a central island, white cabinets, blue lower cabinets, a stainless steel stove, a microwave, and a sink.

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, (22 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$359
includes taxes & fees
24 Nov - 25 Nov
The Main Event Game House on the Huntley Square!
An outdoor patio with stone flooring, a wooden table and chairs, a stone wall, and a fire pit.

7. 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 AU$267
includes taxes & fees
17 Nov - 18 Nov
Little Fox Cottage - A Cozy Riverview Getaway
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 AU$1,931
includes taxes & fees
16 Nov - 17 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 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 AU$1,046
includes taxes & fees
15 Nov - 16 Nov
1905 Victorian close to Lake Geneva. Decorated for the Holidays!
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, (18 reviews)
"Very spacious, clean & great location!"
United States
Ernesta T.
The price is AU$408
includes taxes & fees
19 Nov - 20 Nov
Richmond No. 267 Boutique Loft Apartment
An indoor water park with multiple pools, slides, and a large sign for Moose Mountain Falls.

11. Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark
3.5 star property
Lake Geneva
8.6 out of 10, Excellent, (3,531 reviews)
"Great hotel amazing staff and amazing waterpark"
United States
Lindsey
The price is AU$258
includes taxes & fees
16 Nov - 17 Nov
Timber Ridge Lodge and Waterpark
An indoor swimming pool with wooden walls and a glass 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, (1,276 reviews)
"clean, comfortable and great location"
United States
Marshall
The price is AU$307
includes taxes & fees
15 Nov - 16 Nov
Mill Creek Hotel
A house by a lake with docked boats and a flag.

13. 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)
"This was an amazing property right on the water. It was clean, the host was very helpful and answered questions in a timely manner. We came when it rained which was unfortunate but we still enjoyed our time there!"
United States
Christina C.
The price is AU$451
includes taxes & fees
19 Nov - 20 Nov
This is a VACATION spot with a million dollar view!
A patio area with outdoor seating and a fire feature, surrounded by greenery and overlooking a body of water.

14. 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 AU$357
includes taxes & fees
16 Nov - 17 Nov
Lake Geneva, Fireplace, Pool, Wifi, King Bed
A room with a wooden desk, a bed, a large window, and a brick wall.

15. 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 AU$368
includes taxes & fees
29 Nov - 30 Nov
124 Lofts #4 - Downtown Dundee - Walk to Dining
A dining area with a brick wall, a wooden table, black chairs, and a potted plant.

16. 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 AU$385
includes taxes & fees
16 Nov - 17 Nov
Hidden Gem with Pool View!
A bed with striped bedding, multiple pillows, and framed pictures on the wall.

17. Downtown Lake Geneva LA Suite Walk to Beach Dining Shops Parking

Downtown Lake Geneva LA Suite Walk to Beach Dining Shops Parking
Lake Geneva
10.0 out of 10, Exceptional, (11 reviews)
"Host was very communicative and friendly and helpful. Location and rooms were excellent. "
United States
Michael B.
The price is AU$333
includes taxes & fees
16 Nov - 17 Nov
Downtown Lake Geneva LA Suite Walk to Beach Dining Shops Parking
A hotel room with a bed, a desk, a lamp, a TV, and a framed artwork.

18. 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 AU$338
includes taxes & fees
15 Nov - 16 Nov
124 Lofts #1 - Downtown Dundee - Walk to Dining
A beach with a lifeguard tower, a covered pavilion, and a view of the water and distant land.

19. Stunning Waterfront views & cozy fireplace on the shores of Lake Como. King bed.

Stunning Waterfront views & cozy fireplace on the shores of Lake Como. King bed.
Lake Geneva
10.0 out of 10, Exceptional, (69 reviews)
"Beautiful location"
United States
PENNY H.
Stunning Waterfront views & cozy fireplace on the shores of Lake Como. King bed.
A building with a dark brick facade, numbered 729, featuring a door with a wreath and a mailbox.

20. 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.
Broad St Earth Suite |Amazing Location in the Heart of Town |Parking Available |King & Queen Bedroom
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

Grand Geneva Resort & Spa

Grand Geneva Resort & Spa

10/10 Excellent
"Great, beautiful place"
Baher 2-night trip
Posted 13 hours ago
Grand Geneva Resort & Spa

Find out more about Woodstock

Everything you need to know about Woodstock holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Woodstock holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Woodstock holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Woodstock holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Woodstock. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woodstock holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woodstock holiday rentals we have selected for you start as low as AU$258 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Woodstock rentals

At Expedia, we put the best Woodstock holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Woodstock rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Woodstock holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Woodstock. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Woodstock?

Yes, there are holiday rentals in Woodstock close to McHenry County Fairgrounds, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Woodstock has to offer?

Luxury Lake Geneva cottage w/ sauna + hot tub + geodesic dome on 2-acres: This holiday home rental outside of Woodstock is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Woodstock?

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

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 holiday rentals like in Woodstock?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodstock. Holiday rentals offer extras such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a small group gathering.