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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Woodstock vacation rentals

Exterior

1. The Tailor House

The Tailor House
Woodstock
9.8 out of 10, Exceptional, (56 reviews)
"Amazing stay. So close to everything!"
United States
Brittany H.
$284 nightly
The price is $301
Aug 17 - Aug 18
Total with taxes and fees
The Tailor House
Private kitchen

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, (2 reviews)
"Cute little apartment over the top of a boba shop. There is a little hidden bedroom with a twin bed on the other side of the living room that was so cozy. In the bedroom there is a King size bed with a very comfortable mattress and plenty of closet space. The bathroom is small but easy to use, and the kitchen is large and roomy. We didn’t get to spend much time at the place but we enjoyed the location and the quiet neighborhood. On site workers were also so helpful when we needed an extension...
United States
Callie C.
$170 nightly
The price is $180
Aug 9 - Aug 10
Total with taxes and fees
Lovely 1-bedroom apartment with AC in charming Woodstock
Private kitchen

3. Charming 2-bedroom house with WiFi, AC in fabulous Woodstock

Charming 2-bedroom house with WiFi, AC in fabulous Woodstock
Woodstock
8.0 out of 10, Very Good, (1 review)
"I was very surprised that the property was by itself on a 2 lane road. We initially drove past it because there was nothing on the side of the road with the address. It was next to an odd and ugly"building." It was less than 10 minutes frim town, which was good. The house was clean, but REEKED of mildew. We bought stuff to help with the smell (which we left for future guests), but it was still bad. There was no toaster or microwave, and there was someone elase's Culver's in the freezer....
United States
Anonymous traveler
$362 nightly
The price is $384
Aug 12 - Aug 13
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in fabulous Woodstock
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

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, (26 reviews)
"Awesome home on the property grounds of Georgia's Place Bird Sanctuary. Gracious hosts who rescue Turkeys, chickens, birds and more. What a pleasant stay in the nice little town of Harvard!"
United States
David K.
$181 nightly
The price is $192
Aug 17 - Aug 18
Total with taxes and fees
Sanctuary Woodland Guest House, located next to the conservation area!
TV

5. 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.
$398 nightly
The price is $422
Aug 10 - Aug 11
Total with taxes and fees
Wonder Lake Elegance: Serene 2BR Townhome Retreat
Outdoor dining

6. Spacious 3 Bedroom

Spacious 3 Bedroom
Cary
8.0 out of 10, Very Good, (1 review)
"Conveniently located near restaurants and downtown. Apartment was clean. Nicely decorated. Cute coffee station. Big table in dining area."
United States
Kim B.
$333 nightly
The price is $353
Aug 10 - Aug 11
Total with taxes and fees
Spacious 3 Bedroom
Exterior

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.
$330 nightly
The price is $350
Sep 1 - Sep 2
Total with taxes and fees
The Main Event Game House on the Huntley Square!
Outdoor dining

8. Little Fox Cottage - A Cozy Riverview Getaway

Little Fox Cottage - A Cozy Riverview Getaway
Fox River Grove
10.0 out of 10, Exceptional, (18 reviews)
"Host and amenities were great!"
United States
Jeff P.
$213 nightly
The price is $226
Aug 9 - Aug 10
Total with taxes and fees
Little Fox Cottage - A Cozy Riverview Getaway
Living area

9. Richmond No. 267 Boutique Loft Apartment

Richmond No. 267 Boutique Loft Apartment
Richmond
10.0 out of 10, Exceptional, (15 reviews)
"Very spacious, clean & great location!"
United States
Ernesta T.
$296 nightly
The price is $309
Sep 1 - Sep 2
Total with taxes and fees
Richmond No. 267 Boutique Loft Apartment
Exterior

10. 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
$1,028 nightly
The price is $1,089
Aug 12 - Aug 13
Total with taxes and fees
1905 Victorian Farmhouse close to Lake Geneva.
Marina

11. The Little Farm Fontana 5 min from Geneva Lake!

The Little Farm Fontana 5 min from Geneva Lake!
Fontana-on-Geneva Lake
$227 nightly
The price is $241
Aug 9 - Aug 10
Total with taxes and fees
The Little Farm Fontana 5 min from Geneva Lake!
Marina

12. 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, (27 reviews)
"Great location!! Beautiful place!!!"
United States
Jason C.
$339 nightly
The price is $359
Aug 9 - Aug 10
Total with taxes and fees
This is a VACATION spot with a million dollar view!
Interior

13. 4Bed 3.5Ba Cozy New Construction! Close to Lake Geneva and Lake Elizabeth!

4Bed 3.5Ba Cozy New Construction! Close to Lake Geneva and Lake Elizabeth!
Twin Lakes
10.0 out of 10, Exceptional, (46 reviews)
"Second time at the home - was clean and comfortable."
United States
Leshonda
$440 nightly
The price is $464
Aug 17 - Aug 18
Total with taxes and fees
4Bed 3.5Ba Cozy New Construction! Close to Lake Geneva and Lake Elizabeth!
TV

14. 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, (28 reviews)
"Loved the couches! Quick walk to wonderful restaurants and lake."
United States
Denise A.
$269 nightly
The price is $306
Aug 12 - Aug 13
Total with taxes and fees
Broad St Earth Suite |Amazing Location in the Heart of Town |Parking Available |King & Queen Bedroom
Beach

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

Lake Geneva Getaway, King Bed, Pool, Fireplace
Lake Geneva
10.0 out of 10, Exceptional, (45 reviews)
"Exactly as described — a clean, comfy condo near the lake! The fireplace was a great feature for a chilly spring visit!"
United States
Pamela P.
$264 nightly
The price is $295
Aug 31 - Sep 1
Total with taxes and fees
Lake Geneva Getaway, King Bed, Pool, Fireplace
TV

16. 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, (10 reviews)
"Host was very communicative and friendly and helpful. Location and rooms were excellent. "
United States
Michael B.
$232 nightly
The price is $264
Aug 10 - Aug 11
Total with taxes and fees
Downtown Lake Geneva LA Suite Walk to Beach Dining Shops Parking
Interior

17. The Luxe at Abbey Villa |Gas Fireplace| King Master |Large Covered Balconies |Pool View |Hot Tub

The Luxe at Abbey Villa |Gas Fireplace| King Master |Large Covered Balconies |Pool View |Hot Tub
Fontana-on-Geneva Lake
9.4 out of 10, Exceptional, (15 reviews)
"Clean, nicely appointed, great location. "
United States
Tom R.
$479 nightly
The price is $529
Aug 10 - Aug 11
Total with taxes and fees
The Luxe at Abbey Villa |Gas Fireplace| King Master |Large Covered Balconies |Pool View |Hot Tub
Interior

18. Abbey Villas Condo Steps to Pool Walk to Fontana Beach Dining and Marina

Abbey Villas Condo Steps to Pool Walk to Fontana Beach Dining and Marina
Fontana-on-Geneva Lake
10.0 out of 10, Exceptional, (4 reviews)
"Great place - attentive and welcoming host."
United States
Beth N.
$496 nightly
The price is $548
Sep 3 - Sep 4
Total with taxes and fees
Abbey Villas Condo Steps to Pool Walk to Fontana Beach Dining and Marina
1 bedroom, desk, iron/ironing board, WiFi

19. 124 Lofts #3 - Downtown Dundee - Walk to Dining

124 Lofts #3 - Downtown Dundee - Walk to Dining
West Dundee
10.0 out of 10, Exceptional, (26 reviews)
"We were in town visiting family and it was the perfect spot to stay for a day or two. We loved that it was right above a local cafe (which was also fantastic by the way!!), and the check-in/out process was a breeze! Owner was very communicative, would definitely stay here again!"
United States
Adamm I.
$218 nightly
The price is $243
Aug 10 - Aug 11
Total with taxes and fees
124 Lofts #3 - Downtown Dundee - Walk to Dining
Interior

20. 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, (25 reviews)
"3 bedrooms was great. Very clean. Enjoyed our stay."
United States
Sharon K.
$462 nightly
The price is $468
Aug 30 - Aug 31
Total with taxes and fees
3-bed 2-bath fully remodeled house walking distance to Lake w/ parking for Boat!
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

Country Inn & Suites by Radisson, Hoffman Estates, IL

Country Inn & Suites by Radisson, Hoffman Estates, IL

8/10 Good
"It was pretty good. Stay room is very clean. Bed is very comfortable. The mini fridge is very small and missing a lot of parts. It will be much better if they have updated many fridge in the room also, it has a bit of breakfast items especially no pork items. The comedy different religions."
Atif 1-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Hoffman Estates, 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 $287 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.

Explore a world of travel with Expedia

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?

Does your dog need a vacation? We are people and pet friendly!: Visitors like this Woodstock vacation home rental. It is located near skiing and has a furnished patio, a private yard, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.