Photo by Erik Rowley

Woodstock holiday rentals

We found 57 holiday rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
April 2024
May 2024
Discover a selection of holiday rentals in Woodstock that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll have the best amenities for spending time at your home away from home, such as Wi-Fi and cable TV. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Lively Woodstock will entice you

The area's jazz and opera are just some of the reasons to come on holiday to Woodstock. This welcoming and trendy city entices travellers with its shopping and golfing. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Woodstock

Are you searching for attractions to visit in the area? Venture out of your holiday home and experience everything that makes Woodstock a fun place to get away to. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Santa's Village (18.2 mi / 29.3 km)
  • Moose Mountain Falls Waterpark (19.9 mi / 32 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)
  • Hawks View Golf Club (21.5 mi / 34.7 km)

Exploring the natural landscape of Woodstock

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Woodstock is a great spot to appreciate mother nature. These are some of the area's most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • 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 centre. If you're unable to find a flight that fits your schedule, you could also fly into Chicago, IL (PWK-Chicago Executive), which is 31.3 mi (50.3 km) away.

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

Frequently asked questions

What is the most popular type of holiday home accommodation in Woodstock?

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

How much does it cost to rent a holiday home in Woodstock?

The average price for a holiday 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 cosy 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 Stayz. 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 holiday homes 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 holiday homes and find a holiday home that'll set tails wagging on Stayz.

What are popular home amenities in Woodstock?

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

Are there large group holiday homes in Woodstock?

Yes, you can choose one of two holiday 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 holiday homes in Woodstock that welcome kids?

With three family-friendly holiday homes 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 travelling 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 holiday homes with WiFi in Woodstock?

You can pick from two holiday homes 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 Stayz.

How can I find holiday homes with air conditioning in Woodstock?

Pick your dates and then use the filter tool to search for holiday homes with air conditioning in Woodstock on Stayz. 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 holiday home in Woodstock?

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

How long can I rent a holiday home in Woodstock for?

The amount of time you can book a Woodstock holiday 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 holiday homes may also offer weekly or monthly discounts, so you can have a longer stay for less.

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