Woodstock Holiday Rentals from NZ$284: 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 holiday rentals

A white house with a porch and a chimney, surrounded by a grassy area and a brick path.

1. The Tailor House

Woodstock

Brittany H.

includes taxes & fees

22 Sept - 23 Sept

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 traveller

includes taxes & fees

20 Sept - 21 Sept

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

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.

includes taxes & fees

20 Sept - 21 Sept

4. Wonder Lake Elegance: Serene 2BR Townhome Retreat

Wonder Lake

Ken S.

includes taxes & fees

18 Oct - 19 Oct

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

5. Timber Ridge Lodge and Waterpark

Lake Geneva

Pawel

includes taxes & fees

7 Oct - 8 Oct

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.

includes taxes & fees

21 Sept - 22 Sept

A bedroom with a large bed, two bedside tables with lamps, and a tapestry depicting a waterfall.

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

Harvard

Jamie S.

includes taxes & fees

27 Sept - 28 Sept

A large, two-story house with a wrap-around porch and a stone foundation.

8. 1905 Victorian Farmhouse close to Lake Geneva.

Hebron

Shari

includes taxes & fees

20 Sept - 21 Sept

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

9. Mill Creek Hotel

Lake Geneva

Daniel

includes taxes & fees

1 Oct - 2 Oct

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.

includes taxes & fees

18 Sept - 19 Sept

An outdoor patio with stone flooring, multiple seating areas, and a central fire feature.

11. Modern Lake Geneva Condo With Views

Lake Geneva

includes taxes & fees

21 Sept - 22 Sept

A two-story house with a front porch, a stone exterior on the right side, and a green door.

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

Huntley

BENJAMIN B.

includes taxes & fees

23 Sept - 24 Sept

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

13. Richmond No. 267 Boutique Loft Apartment

Richmond

Ernesta T.

includes taxes & fees

29 Sept - 30 Sept

A house by a lake with docked boats and a flag.

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

fox lake

Jason C.

includes taxes & fees

28 Sept - 29 Sept

A modern living room with a green sofa, a white coffee table, and a ceiling fan.

15. Broad St Earth Suite |Amazing Location in the Heart of Town |Parking Available |King & Queen Bedroom

Lake Geneva

Denise A.

includes taxes & fees

22 Sept - 23 Sept

A spacious living room with a wooden floor, a dining area, and a kitchen in the background.

16. Salem Vacation Home w/ Dock: Steps to Paddock Lake

Salem

includes taxes & fees

18 Sept - 19 Sept

A hotel room with a bed, a desk, a lamp, a TV, and a framed artwork.

17. 124 Lofts #1 - Downtown Dundee - Walk to Dining

West Dundee

Haggard A.

includes taxes & fees

20 Sept - 21 Sept

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

18. Kildahl House - Boutique Farmhouse Suite #1

West Dundee

Thea

includes taxes & fees

4 Oct - 5 Oct

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

19. 124 Lofts #4 - Downtown Dundee - Walk to Dining

West Dundee

Shannon

includes taxes & fees

20 Sept - 21 Sept

20. Kildahl House - Boutique Farmhouse Suite #2

West Dundee

Jen C.

includes taxes & fees

20 Sept - 21 Sept

View all properties

Find holiday rentals that suit your style

Apartments

Aparthotels

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

Hilton Garden Inn Hoffman Estates

10/10 Excellent

"Nice stay, enjoyed visit Nice area"

Timber Ridge Lodge and Waterpark

8/10 Good

"Wish that the person who checked me in gave me information about the hotel. She basically gave me the keycard. And told me where the elevator was. Nothing else. No info about what was on the site. Not even the hours for the water park Found out later that I could have went to the grand cayman and use the amenities there but nope. The hotel was excellent. So very clean. For that part I really thank you but the reception check in not so much."

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 holiday rentals

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

Woodstock holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Woodstock holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Woodstock holiday rentals we have selected for you start as low as NZ$284 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Woodstock rentals

At Expedia, we put the best Woodstock holiday 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 holiday.

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 holiday rentals in Woodstock?

Yes, there are holiday rentals in Woodstock close to McHenry County Fairgrounds, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Woodstock has to offer?

Luxury Lake Geneva cottage w/ sauna + hot tub + geodesic dome on 2-acres: This holiday home rental outside of Woodstock is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Woodstock?

Choose from 8 Expedia holiday rentals in Woodstock for a memorable holiday.

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 holiday rentals like in Woodstock?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodstock. Holiday rentals offer extras such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a small group gathering.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Woodstock holiday 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. Wonder Lake Elegance: Serene 2BR Townhome Retreat

5. Timber Ridge Lodge and Waterpark

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

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

8. 1905 Victorian Farmhouse close to Lake Geneva.

9. Mill Creek Hotel

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

11. Modern Lake Geneva Condo With Views

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

13. Richmond No. 267 Boutique Loft Apartment

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

15. Broad St Earth Suite |Amazing Location in the Heart of Town |Parking Available |King & Queen Bedroom

16. Salem Vacation Home w/ Dock: Steps to Paddock Lake

17. 124 Lofts #1 - Downtown Dundee - Walk to Dining

18. Kildahl House - Boutique Farmhouse Suite #1

19. 124 Lofts #4 - Downtown Dundee - Walk to Dining

20. Kildahl House - Boutique Farmhouse Suite #2

Find holiday rentals that suit your style

Top Woodstock Hotel Reviews

Hilton Garden Inn Hoffman Estates

Comfort Suites Grayslake near Libertyville North

Best Western Plus Elgin - Chicago

Grand Geneva Resort & Spa

Timber Ridge Lodge and Waterpark

Quality Inn & Suites Woodstock near Lake Geneva

Find out more about Woodstock

Frequently asked questions

Go further with the Expedia app