Discover a selection of 87 vacation rentals in Woodstock, IL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $40 per night, and houses and condos are popular options for a stay in Woodstock. Either way, you'll find a rental for everyone's needs.
Destination guide

Head to the lively city of Woodstock

The area's jazz and opera are just a few of the reasons to vacation in Woodstock. This welcoming and trendy city entices travelers with its shopping and golfing. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.


Activities and attractions in and around Woodstock

Are you searching for attractions to visit during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Woodstock has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • McHenry County Fairgrounds (1.7 mi / 2.7 km)
  • Bull Valley Golf Club (2.8 mi / 4.5 km)
  • Craig Woods Golf Club (6 mi / 9.7 km)
  • Crystal Woods Golf Club (6.1 mi / 9.8 km)
  • Terrace Hill Golf Course (11.5 mi / 18.4 km)
  • Hunter Country Club (13.2 mi / 21.3 km)
Natural features

Exploring the natural features in Woodstock

Whether you're an outdoor enthusiast or just want to take in the scenery, Woodstock is a great spot to appreciate mother nature. These are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Emricson Park (0.9 mi / 1.4 km)
  • Veterans Acres Park (8.7 mi / 14 km)
  • Crystal Lake Park (8.7 mi / 14.1 km)
  • McCullom Lake (8.9 mi / 14.3 km)
  • McHenry Shores Beach Park (10.4 mi / 16.7 km)
  • Three Oaks Recreation Area (10.6 mi / 17 km)
How to get there

How to get to and around Woodstock

The nearest airport is in Chicago, IL (DPA-Dupage), located 30.8 mi (49.6 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Chicago, IL (PWK-Chicago Executive), which is 32.1 mi (51.6 km) away.

If you'd prefer to travel by train, the main station is Woodstock Station.

How many vacation rentals are available around Woodstock, IL?

Our 2020 property listings offer a large selection of 87 vacation rentals around Woodstock. From 56 house rentals to 29 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Woodstock?

Vrbo offers a large selection of vacation rentals near lovely places in Woodstock. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Woodstock Square: 205 vacation rentals
  • Woodstock Station: 222 vacation rentals
  • Bull Valley Golf Club: 156 vacation rentals
  • McHenry County Fairgrounds: 195 vacation rentals
  • Woodstock Opera House: 204 vacation rentals

But there are many other points of interest around Woodstock listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Woodstock?

Yes, of course. Vrbo has 56 Houses in Woodstock. Our other popular types of vacation rentals in Woodstock include:

  • Condos/Apartments: 29 rentals available
  • Cabins: 2 rentals available
  • Cottages: 2 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Villas and more.

Can I find a vacation rental with pool in Woodstock?

Yes, you can select your preferred vacation rental with pool among our 43 vacation rentals with pool available in Woodstock. Please use our search bar to access the selection of vacation rentals available.