Woodstock Vacation Rentals from $195: Search Short-Term Rentals

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Our top choices for Woodstock vacation rentals

1. The Tailor House

Woodstock

Brittany H.

$245 nightly

Sep 22 - Sep 23

Total with taxes and fees

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

Woodstock

"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....

Anonymous traveler

$350 nightly

Sep 22 - Sep 23

Total with taxes and fees

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

Woodstock

"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...

Callie C.

$170 nightly

Sep 22 - Sep 23

Total with taxes and fees

4. Timber Ridge Lodge and Waterpark

Lake Geneva

Pawel

$175 nightly

Oct 21 - Oct 22

Total with taxes and fees

5. Wonder Lake Elegance: Serene 2BR Townhome Retreat

Wonder Lake

Ken S.

$344 nightly

Oct 19 - Oct 20

Total with taxes and fees

6. 1905 Victorian Farmhouse close to Lake Geneva.

Hebron

Shari

$1,015 nightly

Sep 22 - Sep 23

Total with taxes and fees

7. Mill Creek Hotel

Lake Geneva

Daniel

$217 nightly

Oct 1 - Oct 2

Total with taxes and fees

8. Terrific 3-bedroom family-friendly house close to everything in charming McHenry

McHenry

Cj D.

$268 nightly

Sep 22 - Sep 23

Total with taxes and fees

9. HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

McHenry

"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...

Brittany B.

$1,458 nightly

Oct 5 - Oct 6

Total with taxes and fees

2 bedrooms, iron/ironing board, WiFi (free), bed sheets

10. Sanctuary Woodland Guest House, located next to the conservation area!

Harvard

Jamie S.

$193 nightly

Sep 27 - Sep 28

Total with taxes and fees

11. The Main Event Game House on the Huntley Square!

Huntley

BENJAMIN B.

$232 nightly

Oct 1 - Oct 2

Total with taxes and fees

12. This is a VACATION spot with a million dollar view!

fox lake

Jason C.

$629 nightly

Sep 28 - Sep 29

Total with taxes and fees

13. Richmond No. 267 Boutique Loft Apartment

Richmond

Ernesta T.

$282 nightly

Sep 24 - Sep 25

Total with taxes and fees

14. Newly Updated Modern, Spacious, and Cozy Condo- Right on the Lake!

Lake Geneva

John L.

$382 nightly

Sep 24 - Sep 25

Total with taxes and fees

1 bedroom, desk, iron/ironing board, WiFi

15. 124 Lofts #1 - Downtown Dundee - Walk to Dining

West Dundee

Haggard A.

$218 nightly

Sep 23 - Sep 24

Total with taxes and fees

16. Chic 3 bedroom Get-a-way in downtown Lake Geneva

Lake Geneva

Sharon R.

$511 nightly

Sep 22 - Sep 23

Total with taxes and fees

17. Little Fox Cottage - A Cozy Riverview Getaway

Fox River Grove

Jeff P.

$181 nightly

Oct 20 - Oct 21

Total with taxes and fees

18. Modern Lake Geneva Condo With Views

Lake Geneva

$720 nightly

Sep 29 - Sep 30

Total with taxes and fees

19. Hot Tub Retreats

Lake Villa

Rosilynn B.

$316 nightly

Sep 22 - Sep 23

Total with taxes and fees

Coffee/tea maker, microwave, oven, stovetop

20. The Ridge Retreat Renovated in 2024 - Steps from Lake Como & The Ridge

Lake Geneva

Katie O.

$502 nightly

Sep 27 - Sep 28

Total with taxes and fees

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Top Woodstock Hotel Reviews

Abbey Resort and Avani Spa

10/10 Excellent

"The staff was friendly and helpfull. The room was great, very comfortable and the view of the Lake and harbor are amazing."

Lodge Geneva National

8/10 Good

"The Craft de Italia Restaurant menu at Lodge Geneva National was very limited. I ordered the pork tenderloin with asparagus. The tenderloin was tasty but was too salty. The asparagus was inedible. It was unchewable. My wife said that it is just a decoration. Then why put it on a food plate. The price of the selection was high enough that it could have included a potato and/or a vegetable. I do not recommend this restaurant. The connected restaurants at nearby Geneva National are too inconvenient to go to, especially at night. The outside pool, bar and fire pit are excellent. The room also was very good."

Quality Inn & Suites Woodstock near Lake Geneva

10/10 Excellent

"Only negative about our stay was there was not an elevator for the second floor rooms and they had booked all of their downstairs rooms. Pool was nice. It is a small pool and not very deep. Was perfect for the kids to play in. And for the adults relax in. Washer and dryer on site was a nice touch. Breakfast was a small but worth the trip down. Bagels with cream cheese options. Dry cereal and oatmeal. Milk. Coffee. Orange and Apple juice. Toast and could make fresh waffles. Yogurt and fresh bananas. Enough to get our crew fed and have a late lunch or early dinner to help cut our food cost. Night staff were great ( I didn't get the ladies name she was the only female front desk staff) and housekeeping were super helpful and kept up with all our needs of extra clean towels. Changing sheets and getting our trash out. All around was a great stay for our 5 days"

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 $195 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.

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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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Check prices for these dates

Our top choices for Woodstock vacation rentals

1. The Tailor House

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

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

4. Timber Ridge Lodge and Waterpark

5. Wonder Lake Elegance: Serene 2BR Townhome Retreat

6. 1905 Victorian Farmhouse close to Lake Geneva.

7. Mill Creek Hotel

8. Terrific 3-bedroom family-friendly house close to everything in charming McHenry

9. HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

10. Sanctuary Woodland Guest House, located next to the conservation area!

11. The Main Event Game House on the Huntley Square!

12. This is a VACATION spot with a million dollar view!

13. Richmond No. 267 Boutique Loft Apartment

14. Newly Updated Modern, Spacious, and Cozy Condo- Right on the Lake!

15. 124 Lofts #1 - Downtown Dundee - Walk to Dining

16. Chic 3 bedroom Get-a-way in downtown Lake Geneva

17. Little Fox Cottage - A Cozy Riverview Getaway

18. Modern Lake Geneva Condo With Views

19. Hot Tub Retreats

20. The Ridge Retreat Renovated in 2024 - Steps from Lake Como & The Ridge

Find vacation rentals that suit your style

Top Woodstock Hotel Reviews

Abbey Resort and Avani Spa

AmericInn by Wyndham Woodstock IL

Lodge Geneva National

Harbor Shores on Lake Geneva

Quality Inn & Suites Woodstock near Lake Geneva

Find out more about Woodstock

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