Photo by Erik Rowley

Woodstock vacation rentals

We found 55 vacation rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
May 2024
June 2024
Discover a selection of vacation rentals in Woodstock that are perfect for your trip. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll have the amenities you expect and more, which might include cable TV and a washer and dryer. Whatever you're looking for, you'll find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

Lively Woodstock will entice you

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. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Woodstock

Do you want to find attractions to visit in the area? 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 top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Santa's Village (18.2 mi / 29.3 km)
  • Moose Mountain Falls Waterpark (19.9 mi / 32 km)
  • Studio Winery (20 mi / 32.2 km)
  • Geneva National Golf Club (20.1 mi / 32.3 km)
  • Lake Geneva Balloon Company (20.2 mi / 32.6 km)
  • The Mountain Top at Grand Geneva Resort (20.8 mi / 33.4 km)

Exploring the natural landscape of Woodstock

Whether you're looking for adventure or just want to spend some time taking in the scenery, Woodstock is a great place to get outside. These are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Crystal Lake Park (8 mi / 12.8 km)
  • Petersen Park Beach (9.1 mi / 14.6 km)
  • Chain 'O Lakes State Park (16.8 mi / 27 km)
  • Twin Lakes Private Park Beach (17 mi / 27.3 km)
  • Big Foot Beach State Park (17.4 mi / 28 km)
  • Geneva Lake (17.6 mi / 28.3 km)

How to get to and around Woodstock

The nearest airport is in Chicago, IL (DPA-Dupage), located 29.9 mi (48.1 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Chicago, IL (PWK-Chicago Executive), which is 31.3 mi (50.3 km) away.

If you prefer train travel, the main station serving the city is Woodstock Station.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Woodstock?

Houses are the most popular kind of vacation rental in Woodstock, according to our data. Even if you've got a different idea about what you'd like, Vrbo has properties in all sizes and shapes. Look through our options to find your perfect fit.

How much does it cost to rent a vacation rental in Woodstock?

The average price for a vacation home in Woodstock is based on several factors, including length of stay, season and property type. Whether you're searching for a sprawling villa with a pool or a cozy condo just for the two of you, just enter your dates of travel to discover stays with terrific value.

How much does it cost to rent a beach house in Woodstock?

When you travel and the style and size of the property will influence how much you'll pay for your beachside escape. Type in your Woodstock travel dates to view your available options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use our filters to pick the amenities and features you want.

Are there pet-friendly vacation rentals in Woodstock?

With three properties that host four-legged guests, your little buddy can join you on your Woodstock getaway. Use our filter tool to search our pet-friendly vacation rentals and find a vacation home that'll set tails wagging on Vrbo.

What are popular rental amenities in Woodstock?

A fireplace, a barbecue grill and a water view head the list of most popular rental amenities in Woodstock. Whether you plan to travel alone, with your better half or as a family, Vrbo can help you find a vacation rental that fits your style with a load of extras you'll love.

Are there large group vacation rentals in Woodstock?

Yes, you can choose one of two vacation homes in Woodstock that can accommodate a group of five or more people. From family trips to events like a friend's birthday, these stays have ample space to kick back with the people that matter the most.

Are there vacation rentals in Woodstock that welcome kids?

With three family-friendly vacation rentals available in Woodstock, now is a superb time to introduce your children to the thrills of travel. Simply click on our "Properties good for families" filter box to view stays that come with conveniences ideal for traveling families, like multiple bedrooms, yards, bunk beds and hot tubs.

What are the top attractions for families in Woodstock?

Keep the kids busy at these leading family-friendly attractions in Woodstock:

  • Main Beach
  • West Beach
  • Petersen Park Beach

Are there vacation rentals with WiFi in Woodstock?

You can pick from two vacation rentals with WiFi in Woodstock. If you want to disconnect from daily life during your escape, but still need to be connected to the internet, these getaways have just what you need. Narrow your search by applying the WiFi filter on Vrbo.

How can I find vacation rentals with air conditioning in Woodstock?

Pick your dates and then use the filter tool to search for vacation rentals with air conditioning in Woodstock on Vrbo. With three air-conditioned properties to choose from here, you can enjoy a cool and comfortable break.

How old do you have to be to rent a vacation rental in Woodstock?

The age limit can differ across properties on Vrbo, so double-check the rules of the vacation home in Woodstock you want. But usually, it's 16, 18 or 21.

How long can I rent a vacation rental in Woodstock for?

The amount of time you can book a Woodstock vacation home for is up to the property. Just tap in your dates of travel to view options that offer long-term stays. They have the things you need to make your extended getaway more convenient and enjoyable, such as kitchens and yards. Some vacation homes may also offer weekly or monthly discounts, so you can have a longer stay for less.

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