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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (56 reviews)
"Amazing stay. So close to everything!"
United States
Brittany H.
$229 nightly
The price is $243
Oct 1 - Oct 2
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
8.0 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
Sep 27 - Sep 28
Total with taxes and fees
Lovely 1-bedroom apartment with AC in charming Woodstock

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
$352 nightly
The price is $373
Sep 24 - Sep 25
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in fabulous Woodstock
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.
$193 nightly
The price is $205
Sep 27 - Sep 28
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.

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, (12 reviews)
"Nearby lots of restaurants and business as well as a nice park."
United States
Cj D.
$278 nightly
The price is $295
Sep 27 - Sep 28
Total with taxes and fees
Terrific 3-bedroom family-friendly house close to everything in charming McHenry

6. 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.
$368 nightly
The price is $390
Oct 19 - Oct 20
Total with taxes and fees
Wonder Lake Elegance: Serene 2BR Townhome Retreat
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.
$232 nightly
The price is $246
Oct 1 - Oct 2
Total with taxes and fees
The Main Event Game House on the Huntley Square!
A spacious living area with a grey sofa, wooden flooring, and a kitchen area with a bar.

8. 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.
$282 nightly
The price is $293
Sep 24 - Sep 25
Total with taxes and fees
Richmond No. 267 Boutique Loft Apartment
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
10.0 out of 10, Exceptional, (19 reviews)
"Host and amenities were great!"
United States
Jeff P.
$201 nightly
The price is $213
Sep 27 - Sep 28
Total with taxes and fees
Little Fox Cottage - A Cozy Riverview Getaway
A modern living room with a green sofa, a white coffee table, and a ceiling fan.

10. 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, (29 reviews)
"Loved the couches! Quick walk to wonderful restaurants and lake."
United States
Denise A.
$262 nightly
The price is $297
Sep 28 - Sep 29
Total with taxes and fees
Broad St Earth Suite |Amazing Location in the Heart of Town |Parking Available |King & Queen Bedroom
An outdoor patio with stone flooring, multiple seating areas, and a central fire feature.

11. Modern Lake Geneva Condo With Views

Modern Lake Geneva Condo With Views
3.5 star property
Lake Geneva
$718 nightly
The price is $800
Sep 27 - Sep 28
Total with taxes and fees
Modern Lake Geneva Condo With Views
A room with a large wooden-framed window, a wooden bench, and a view of a deck and garden.

12. 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
Sep 27 - Sep 28
Total with taxes and fees
1905 Victorian Farmhouse close to Lake Geneva.
A spacious kitchen with a large island, wooden beams, and pendant lighting.

13. 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
9.8 out of 10, Exceptional, (7 reviews)
"Great place - attentive and welcoming host."
United States
Beth N.
$425 nightly
The price is $470
Sep 30 - Oct 1
Total with taxes and fees
Abbey Villas Condo Steps to Pool Walk to Fontana Beach Dining and Marina
An indoor water park with a 'Welcome' sign, slides, and a hot tub area.

14. Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark
3.5 star property
Lake Geneva
8.6 out of 10, Excellent, (3,452 reviews)
"Great place to bring kids."
United States
Pawel
$182 nightly
The price is $203
Oct 13 - Oct 14
Total with taxes and fees
Timber Ridge Lodge and Waterpark
A swimming pool with a 5ft depth marker, surrounded by lounge chairs and a stone wall.

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

LG 1+1 Condo on Lakeshore - pool - walk to Lake
Lake Geneva
$463 nightly
The price is $496
Oct 19 - Oct 20
Total with taxes and fees
LG 1+1 Condo on Lakeshore - pool - walk to Lake
A beach with a lifeguard tower, a building with a sign for 'Boat Tours', and a clear view of the water.

16. 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.
$244 nightly
The price is $272
Oct 21 - Oct 22
Total with taxes and fees
Lake Geneva, Fireplace, Pool, Wifi, King Bed
A two-story house with a swimming pool, outdoor seating, and a stone chimney.

17. 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, (46 reviews)
"We stayed with our wedding bridal party here, and this massive and beautiful house was the perfect location to spend the weekend with all of our best friends! The house is obviously gorgeous, and the pool, hot tub, fire pit and pool table added an extra tier of fun. We hosted our rehearsal dinner on the back lawn and rented tables and chairs through the property, which was incredibly convenient.The property managers were communicative and very helpful throughout the process. I highly...
United States
Brittany B.
$1,521 nightly
The price is $1,612
Oct 5 - Oct 6
Total with taxes and fees
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
A beach with a lifeguard tower, a building with a sign for 'Boat Tours', and a clear view of the water.

18. Lake Geneva Retreat, Fireplace, Pool, WiFi

Lake Geneva Retreat, Fireplace, Pool, WiFi
Lake Geneva
10.0 out of 10, Exceptional, (35 reviews)
"A nice, comfortable place to stay in Lake Geneva... just a few minutes' walk from Mars Resort supper club on Lake Como, which was the entire reason for our trip. The condo was spacious and clean, and the host was great to work with. I highly recommend this spot for a Lake Geneva getaway!"
United States
Julie F.
$253 nightly
The price is $282
Sep 24 - Sep 25
Total with taxes and fees
Lake Geneva Retreat, Fireplace, Pool, WiFi
A dining area with a brick wall, a wooden table, black chairs, and a potted plant.

19. Hidden Gem with Pool View!

Hidden Gem with Pool View!
Lake Geneva
10.0 out of 10, Exceptional, (43 reviews)
"Everything was great Love the room and the area"
United States
Thomas P.
$252 nightly
The price is $281
Oct 1 - Oct 2
Total with taxes and fees
Hidden Gem with Pool View!
A wicker tray with a pitcher and glasses on a wooden table on a porch.

20. Kildahl House - Boutique Farmhouse Suite #2

Kildahl House - Boutique Farmhouse Suite #2
West Dundee
10.0 out of 10, Exceptional, (18 reviews)
"Always a pleasure to stay here when visiting my son!"
United States
Jen C.
$236 nightly
The price is $263
Sep 27 - Sep 28
Total with taxes and fees
Kildahl House - Boutique Farmhouse Suite #2
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

Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

10/10 Excellent
"Booked 2 of the 2 bedrooms and they were completely spacious. Great for my family size. The rooms were clean and didn’t have an odor. The waterpark had everyone’s attention. Had something for everyone to do."
Tationne 1-night trip
Posted 19 hours ago
Timber Ridge Lodge and Waterpark

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 $203 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?

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.