Woodstock Holiday Rentals from AU$213: Search Short-Term Rentals

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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

Brandon B.

includes taxes & fees

1 Oct - 2 Oct

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.

includes taxes & fees

29 Sept - 30 Sept

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 traveller

includes taxes & fees

29 Sept - 30 Sept

A kitchen with a dark wooden table, white cabinets, and a sliding barn door.

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

McHenry

Cj D.

includes taxes & fees

5 Oct - 6 Oct

5. Wonder Lake Elegance: Serene 2BR Townhome Retreat

Wonder Lake

Ken S.

includes taxes & fees

8 Oct - 9 Oct

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

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

Harvard

Jamie S.

includes taxes & fees

25 Oct - 26 Oct

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.

includes taxes & fees

1 Oct - 2 Oct

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.

includes taxes & fees

1 Oct - 2 Oct

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Top Woodstock Hotel Reviews

Timber Ridge Lodge and Waterpark

10/10 Excellent

"We had such a wonderful stay at Timber Ridge Lodge! The hotel was very clean, comfortable, and perfect for our family. The kids had so much fun, and we really enjoyed the indoor water park. Everything was great, and we had such a relaxing family getaway. We definitely plan to come back again! ❤️"

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 favourite 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 depend 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 AU$213 per night. Entering your travel dates in the search wizard might find you 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.

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Check prices for these dates

Our top choices for Woodstock holiday 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. Terrific 3-bedroom family-friendly house close to everything in charming McHenry

5. Wonder Lake Elegance: Serene 2BR Townhome Retreat

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

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

11. Timber Ridge Lodge and Waterpark

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

13. Modern Lake Geneva Condo With Views

14. Cozy Lake Geneva, King Bed, Fireplace & Pool

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

16. Relaxing Getaway/StepsToLake/Pool/Tennis near DT Lake Geneva

17. Cozy 2BR Lake Geneva Home, Fire Pit, Sleeps 6

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

19. Downtown Lake Geneva LA Suite Walk to Beach Dining Shops Parking

20. Quaint, quiet condo minutes from Lake Geneva

Find holiday rentals that suit your style

Top Woodstock Hotel Reviews

Timber Ridge Lodge and Waterpark

Lodge Geneva National

Elgin Inn

Lake Lawn Resort

Quality Inn & Suites Woodstock near Lake Geneva

Find out more about Woodstock

Frequently asked questions

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