Woodstock Vacation Rentals from ￥23,221: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

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

Woodstock

Brandon B.

￥39,709 total

includes taxes & fees

Oct 6 - Oct 7

A red house with a porch, a wooden staircase, and a flag.

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

Woodstock

Beth B.

￥28,365 total

includes taxes & fees

Oct 4 - Oct 5

3. 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

￥58,397 total

includes taxes & fees

Oct 3 - Oct 4

4. Wonder Lake Elegance: Serene 2BR Townhome Retreat

Wonder Lake

Ken S.

￥61,046 total

includes taxes & fees

Oct 13 - Oct 14

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!

Harvard

Jamie S.

￥31,535 total

includes taxes & fees

Oct 25 - Oct 26

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

McHenry

Cj D.

￥46,382 total

includes taxes & fees

Oct 5 - Oct 6

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!

Huntley

BENJAMIN B.

￥40,710 total

includes taxes & fees

Oct 4 - Oct 5

An outdoor patio with stone flooring, a wooden table and chairs, a stone wall, and a fire pit.

8. Little Fox Cottage - A Cozy Riverview Getaway

Fox River Grove

Jeff P.

￥29,728 total

includes taxes & fees

Oct 5 - Oct 6

A spacious living area with a grey sofa, wooden flooring, and a kitchen area with a bar.

9. Richmond No. 267 Boutique Loft Apartment

Richmond

Ernesta T.

￥45,834 total

includes taxes & fees

Oct 4 - Oct 5

A two-story house with a swimming pool, outdoor seating, and a stone chimney.

10. 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.

￥261,488 total

includes taxes & fees

Oct 4 - Oct 5

A two-story house with a front porch, a mailbox, and a number '10216' on the door.

11. 1905 Victorian Farmhouse close to Lake Geneva.

Hebron

Shari

￥141,689 total

includes taxes & fees

Oct 19 - Oct 20

An indoor water park with a 'Welcome' sign, slides, and a hot tub area.

12. Timber Ridge Lodge and Waterpark

Lake Geneva

Edgar

￥23,221 total

includes taxes & fees

Oct 20 - Oct 21

A building with a sign reading "Angels Home & Garden" and a sign for "Geneva Lakes Vacations".

13. Second Level Elevated Escape |The Crows Nest | 1.9 miles to Fontana and Abbey Resort

Walworth

Olivia

￥65,979 total

includes taxes & fees

Oct 9 - Oct 10

An indoor swimming pool with wooden walls and ceiling, surrounded by lounge chairs and potted plants.

14. Mill Creek Hotel

Lake Geneva

Daniel

￥33,362 total

includes taxes & fees

Nov 1 - Nov 2

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

Lake Geneva

￥77,377 total

includes taxes & fees

Oct 20 - Oct 21

A wicker tray with a pitcher and glasses on a wooden table on a porch.

16. Kildahl House - Boutique Farmhouse Suite #1

West Dundee

Thea

￥41,355 total

includes taxes & fees

Oct 6 - Oct 7

A bedroom with a brick wall, a bed, a desk, and a window with a view.

17. 124 Lofts #4 - Downtown Dundee - Walk to Dining

West Dundee

Shannon

￥38,202 total

includes taxes & fees

Oct 6 - Oct 7

A beach with a lifeguard tower, a building with a sign reading 'Boat Tours & Charter,' and a sandy shore with people and beach equipment.

18. Lake Geneva, Fireplace, Pool, Wifi, King Bed

Lake Geneva

SUZY R.

￥44,344 total

includes taxes & fees

Nov 2 - Nov 3

A spacious kitchen with a large island, wooden beams, and pendant lighting.

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

Fontana-on-Geneva Lake

Beth N.

￥74,222 total

includes taxes & fees

Oct 8 - Oct 9

A dining area with a brick wall, a wooden table, black chairs, and a potted plant.

20. Hidden Gem with Pool View!

Lake Geneva

Thomas P.

￥44,060 total

includes taxes & fees

Oct 4 - Oct 5

View all properties

Find vacation rentals that suit your style

Cabins

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Woodstock Hotel Reviews

Harbor Shores on Lake Geneva

10/10 Excellent

"Very nice and comfortable stay. Loved the room. It was really cozy and relaxing"

Best Western Plus Elgin - Chicago

10/10 Excellent

"The property was really nice. Very clean room, I had the balcony room which was an extra nice touch. Great patio area out back but was unable to use due to rain. Breakfast was really nice and the front lobby area was very nice and well furnished to eat breakfast or just to sit and talk with others. Definitely recommend this property."

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

Search for holiday rentals in Woodstock on Expedia! You can easily find your home rentals, villas, holiday apartments in Woodstock using one of the methods below:

View our selection of featured holiday rentals in Woodstock
Use the map to find apartments and other holiday homes in the Woodstock neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Woodstock while they last

Look no further and take a look at our great range of rental properties in Woodstock!

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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Woodstock vacation rentals

1. The Tailor House

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

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

4. Wonder Lake Elegance: Serene 2BR Townhome Retreat

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

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

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

8. Little Fox Cottage - A Cozy Riverview Getaway

9. Richmond No. 267 Boutique Loft Apartment

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

11. 1905 Victorian Farmhouse close to Lake Geneva.

12. Timber Ridge Lodge and Waterpark

13. Second Level Elevated Escape |The Crows Nest | 1.9 miles to Fontana and Abbey Resort

14. Mill Creek Hotel

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

16. Kildahl House - Boutique Farmhouse Suite #1

17. 124 Lofts #4 - Downtown Dundee - Walk to Dining

18. Lake Geneva, Fireplace, Pool, Wifi, King Bed

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

20. Hidden Gem with Pool View!

Find vacation rentals that suit your style

Top Woodstock Hotel Reviews

Harbor Shores on Lake Geneva

Best Western Plus Elgin - Chicago

Comfort Suites Lake Geneva East

Quality Inn & Suites Woodstock near Lake Geneva

Find out more about Woodstock

Frequently asked questions

Go further with the Expedia app