Woodstock Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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, (58 reviews)
"Thank you. Would definitely stay again."
United States
Brandon B.
$228 nightly
The price is $242
Nov 8 - Nov 9
Total with taxes and fees
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
8.6 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.
$156 nightly
The price is $165
Nov 9 - Nov 10
Total with taxes and fees
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.
$329 nightly
The price is $349
Nov 8 - Nov 9
Total with taxes and fees
Wonder Lake Elegance: Serene 2BR Townhome Retreat
A kitchen with a view of a lake, wooden cabinets, a dining area with a table and chairs, and a kitchen island.

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.
$488 nightly
The price is $517
Nov 8 - Nov 9
Total with taxes and fees
5-bedroom Lakefront Getaway on Private Wonder Lake – Sleeps 8
A bedroom with a large bed, two bedside tables with lamps, and a tapestry depicting a waterfall.

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.
$171 nightly
The price is $181
Nov 30 - Dec 1
Total with taxes and fees
Sanctuary Woodland Guest House, located next to the conservation area!
A kitchen with a dark wooden table, white cabinets, and a sliding barn door.

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.
$318 nightly
The price is $337
Nov 8 - Nov 9
Total with taxes and fees
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.

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.
$231 nightly
The price is $245
Nov 8 - Nov 9
Total with taxes and fees
The Main Event Game House on the Huntley Square!
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.
$1,225 nightly
The price is $1,298
Nov 9 - Nov 10
Total with taxes and fees
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
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.
$170 nightly
The price is $180
Nov 15 - Nov 16
Total with taxes and fees
Little Fox Cottage - A Cozy Riverview Getaway
A two-story house with a front porch, a mailbox, and a number '10216' on the door.

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
$797 nightly
The price is $845
Nov 7 - Nov 8
Total with taxes and fees
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.

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.
$257 nightly
The price is $267
Nov 8 - Nov 9
Total with taxes and fees
Richmond No. 267 Boutique Loft Apartment
An indoor water park with a 'Welcome' sign, slides, and a hot tub area.

12. Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark
3.5 star property
Lake Geneva
8.6 out of 10, Excellent, (3,521 reviews)
"Great hotel amazing staff and amazing waterpark"
United States
Lindsey
$160 nightly
The price is $178
Nov 10 - Nov 11
Total with taxes and fees
Timber Ridge Lodge and Waterpark
An indoor swimming pool with wooden walls and ceiling, surrounded by lounge chairs and potted plants.

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
$186 nightly
The price is $211
Nov 9 - Nov 10
Total with taxes and fees
Mill Creek Hotel
A house by a lake with docked boats and a flag.

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.
$296 nightly
The price is $314
Nov 11 - Nov 12
Total with taxes and fees
This is a VACATION spot with a million dollar view!
A beach with a lifeguard tower, a building with a sign reading 'Boat Tours & Charter,' and a sandy shore with people and beach equipment.

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.
$226 nightly
The price is $252
Nov 8 - Nov 9
Total with taxes and fees
Lake Geneva, Fireplace, Pool, Wifi, King Bed
A bedroom with a brick wall, a bed, a desk, and a window with a view.

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.
$208 nightly
The price is $232
Nov 9 - Nov 10
Total with taxes and fees
124 Lofts #4 - Downtown Dundee - Walk to Dining
A modern living room with a green sofa, a white coffee table, and a ceiling fan.

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.
$248 nightly
The price is $282
Nov 8 - Nov 9
Total with taxes and fees
Broad St Earth Suite |Amazing Location in the Heart of Town |Parking Available |King & Queen Bedroom
A modern living room with a grey sofa, a round wooden coffee table, a flat-screen TV mounted on the wall, and a director's chair.

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.
$365 nightly
The price is $414
Nov 8 - Nov 9
Total with taxes and fees
Blue Beach Cottage - 5 Minute Walk to Private Beach!
A living room with a fireplace, a TV mounted on the wall, a balcony with a view of the outdoors, and a sign with motivational phrases.

19. Modern Lake Geneva Condo With Views

Modern Lake Geneva Condo With Views
3.5 star property
Lake Geneva
$700 nightly
The price is $780
Dec 1 - Dec 2
Total with taxes and fees
Modern Lake Geneva Condo With Views
A dining area with a brick wall, a wooden table, black chairs, and a potted plant.

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.
$228 nightly
The price is $254
Nov 8 - Nov 9
Total with taxes and fees
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

A modern hotel room with a large mirror, a bathtub, a flat-screen TV, a sofa, and a large window.
AmericInn by Wyndham Woodstock IL

AmericInn by Wyndham Woodstock IL

AmericInn by Wyndham Woodstock IL
Woodstock

10/10 Excellent

Clean room, nice pool and exercise room. Wonderful breakfast provided with friendly attendant. Desk staff friendly and helpful with local information and directions.
United States
Anonymous traveler
Reviewed August 14, 2017
AmericInn by Wyndham Woodstock IL

Find out more about Woodstock

Everything you need to know about Woodstock vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Woodstock vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Woodstock vacation 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 low season months. For more hustle and bustle, you may prefer to visit Woodstock in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $163 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Woodstock rentals

At Expedia, we put the best Woodstock vacation 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 vacation.

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 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.

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