Woodstock holiday rentals

We found 73 holiday rentals — enter your dates for availability
Discover a selection of 8 homes and other 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.

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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:

  • Bull Valley Golf Club (2 mi / 3.3 km)
  • Santa's Village (18.2 mi / 29.3 km)
  • Dan Patch Stables (19.6 mi / 31.5 km)
  • Moose Mountain Falls Waterpark (19.9 mi / 32 km)
  • Geneva Lake Distilling + Winery (20.1 mi / 32.3 km)
  • Geneva National Golf Club (20.1 mi / 32.3 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:

  • Main Beach (7.8 mi / 12.6 km)
  • Crystal Lake Park (8 mi / 12.8 km)
  • Petersen Park Beach (9.1 mi / 14.6 km)
  • Three Oaks Recreation Area (10 mi / 16.1 km)
  • Lake Elizabeth (16.1 mi / 25.9 km)
  • Twin Lakes Private Park Beach (17 mi / 27.3 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 best area to stay in Woodstock when booking a holiday rental?
When looking for the best area to stay in Woodstock, Illinois for a holiday rental, the historic downtown area is an excellent choice. This charming neighbourhood boasts a rich history and a vibrant setting, making it ideal for visitors seeking a blend of culture and convenience. Here, you'll find a delightful array of shops, restaurants, and cafes, all within walking distance. One of the top attractions in downtown Woodstock is the Old McHenry County Courthouse, an architectural gem that often hosts events and exhibitions. Additionally, the nearby Woodstock Opera House frequently showcases live performances and cultural events, providing an engaging experience for guests.Another appealing area to consider is the picturesque residential neighbourhoods surrounding the downtown, which offer a tranquil atmosphere while still being close to the action. These areas often feature beautiful historic homes and tree-lined streets, superb for leisurely strolls. Staying here provides easy access to both the scenic parks and the vibrant community events that Woodstock is known for.
What is the most popular type of holiday rental accomodation in Woodstock?
In Woodstock, holiday houses are the most popular type of holiday rental, with several available throughout the area. These properties typically offer spacious layouts, including multiple bedrooms and fully equipped kitchens, making them ideal for families or groups. Many holiday houses also feature outdoor spaces such as gardens or patios, great for relaxing after a day of exploring the charming downtown area or enjoying local events like the Woodstock Opera House performances.
Are there any family house rentals in Woodstock?
In Woodstock, Illinois, there are several family-friendly house rentals available, making it a great spot for a family getaway. Visitors can find properties in various neighbourhoods that cater to families, often featuring spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces for children to play. Many homes come with amenities such as Wi-Fi and laundry facilities, ensuring a comfortable stay.The town itself is steeped in charm, with attractions like the historic Woodstock Square, known for its quaint shops and the iconic theatre, where families can enjoy local performances. Additionally, nearby parks provide opportunities for outdoor activities, from picnics to hiking trails.
Can I rent a holiday home with a pool or hot tub in Woodstock?
In Woodstock, Illinois, there are several holiday homes available for rent that feature pools and hot tubs, providing a delightful option for those looking to relax and unwind during their stay. This charming town, known for its historic square and picturesque surroundings, offers a variety of properties that cater to families and groups seeking both comfort and leisure.Travellers can expect amenities such as private swimming pools, hot tubs for soothing relaxation, spacious outdoor areas for gatherings, and fully equipped kitchens, superb for preparing meals together. Many rentals also include features like fire pits, patios, and lush gardens, enhancing the outdoor experience.
Are there pet-friendly house rentals in Woodstock?
In Woodstock, there are several pet-friendly house rentals available that cater to travellers looking to enjoy a comfortable stay with their furry companions. Many of these rentals are situated in peaceful residential areas, offering amenities such as spacious yards, fully equipped kitchens, and cosy living spaces that make it easy for families or groups to unwind.The town itself is known for its charming historic district, where visitors can explore local shops and cafes that often welcome pets. Additionally, nearby parks, such as Emricson Park and the expansive Woodstock City Park, provide excellent opportunities for outdoor activities with pets, featuring walking trails and open spaces for play.
Are there any remote work holiday rentals in Woodstock?
In Woodstock, Illinois, there are several remote work-friendly holiday rentals available, making it an ideal spot for those looking to combine work with leisure. Many of these properties come equipped with essential amenities for remote work, including reliable Wi-Fi, desks, and comfortable chairs, ensuring a productive environment.Travellers can expect to find homes with spacious living areas that create a pleasant atmosphere to balance work and relaxation. The charming town offers a variety of local attractions, such as the historic Woodstock Square, where visitors can enjoy quaint shops and eateries. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Woodstock?
In Woodstock, popular rental amenities include kitchens, which allow guests to prepare their own meals, contributing to a cozy feel. Many rentals also feature workspaces with desks and desk chairs, suiting those needing to work remotely or study during their stay. Families will appreciate the presence of children's books, adding a thoughtful touch for younger guests. Additionally, coffee and tea makers are commonly provided, ensuring that guests can enjoy their favourite hot beverages at their convenience.
When is the best time to visit Woodstock for a holiday rental?
The best time to visit Woodstock for a holiday rental is during the peak season from June to August, with July being the most popular month. This vibrant period attracts families and outdoor enthusiasts eager to enjoy the warm weather and partake in local festivities. With temperatures typically ranging from the mid-teens to low 30s Celsius, it's ideal for exploring the charming downtown area, hiking in nearby parks, or enjoying the various events that take place throughout the summer.During these months, you can immerse yourself in the lively option of Woodstock, where visitors can take advantage of outdoor activities, such as kayaking on the Kishwaukee River or attending local fairs. The town's picturesque setting and welcoming community make it an enjoyable destination for everyone.For those looking for a more budget-friendly option, consider visiting in December. While it's the low season, the holiday spirit comes alive in Woodstock with beautiful decorations and festive events, offering a unique charm that many find delightful. This quieter time allows for a more relaxed experience, superb for cosy getaways and enjoying the seasonal festivities.Ultimately, your choice will depend on whether you prefer the bustling summer excitement or the serene winter charm that Woodstock has to offer.
What are the top attractions in Woodstock?
In Woodstock, Illinois, visitors can engage in a charming blend of history and nature. The historic Woodstock Square is a focal point, featuring beautiful architecture, unique shops, and the iconic Old Courthouse, which adds to the town's quaint atmosphere. This area often hosts seasonal events and festivals, making it a vibrant spot for both locals and tourists.Just a short distance from the square, the Woodstock Opera House is a great attraction, offering a range of performances and cultural events throughout the year. For those who enjoy the outdoors, the nearby Emricson Park provides ample green space, walking trails, and picnic areas, great for a leisurely day. The park is also home to a variety of recreational facilities, including sports fields and a playground.Another highlight is the Bull Valley Golf Club, which offers a picturesque setting for golf enthusiasts. The scenic views and well-maintained course make it a popular destination.
Are all fees included in the Woodstock holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Woodstock holiday homes with parking?
Stayz offers a wide selection of holiday homes in Woodstock with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Woodstock holiday homes?
You can find great discounts on holiday homes in Woodstock on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Woodstock holiday home booking on Stayz?
To find Woodstock holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Woodstock?
A long-stay holiday home in Woodstock is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Woodstock holiday home?
Book your Woodstock holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Woodstock?
Prices for holiday homes in Woodstock vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Woodstock to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.