Photo by Erik Rowley

Woodstock vacation rentals

We found 54 vacation rentals — enter your dates for availability

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.

Vacation rentals with weekly discounts - Woodstock

Showing deals for:Nov 21 - Nov 28

Image gallery for 6 bd Country Estate on 28 Acres near Lk Geneva w/ Ponds, Trails, Fenced Dog-park

Property grounds
9.6 out of 10 rating
Exceptional
(25 reviews)

6 bd Country Estate on 28 Acres near Lk Geneva w/ Ponds, Trails, Fenced Dog-park

Marengo, IL

15% off
Price is CA $1,695
CA $14,227 total
includes taxes & fees
6 bd Country Estate on 28 Acres near Lk Geneva w/ Ponds, Trails, Fenced Dog-park

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Find out more about Woodstock

Find out more about Woodstock

Why visit Woodstock

  1. Scenic outdoor activities: Enjoy beautiful beaches, urban parks, and nature preserves perfect for family-friendly adventures.
  2. Charming accommodations: Choose from cozy cottages, private vacation homes, and spacious condos for a comfortable stay.
  3. Welcoming atmosphere: Experience a friendly vibe that makes Woodstock ideal for budget-friendly family getaways.
  4. Exploration opportunities: Discover nearby towns and picturesque landscapes, perfect for creating cherished memories.
  5. Year-round attractions: Engage in diverse activities, whether in winter or summer, ensuring a memorable vacation.

Popular types of accommodation in Woodstock

If you're exploring vacation rentals in Woodstock, you're in for a treat! The most sought-after accommodations include houses, condos, and apartments, ensuring you'll find the perfect holiday home for your stay. Whether you're searching for a cozy retreat or a spacious getaway, our selection of holiday rentals has something for everyone. Enjoy transparency and savings while discovering your ideal home away from home in this charming Canadian destination.

  • Houses: The top choice for visitors to Woodstock, offering spacious and comfortable settings ideal for families or groups.
  • Condos: A popular option, providing modern amenities and convenience in the heart of Woodstock.
  • Apartments: A versatile accommodation type, perfect for those seeking a home-like feel during their stay.
  • Cottages: Quaint and charming, these options offer a delightful retreat for those looking to relax.
  • Cabins: Ideal for nature enthusiasts, providing a rustic escape surrounded by beautiful landscapes.**

Top attractions in Woodstock

Woodstock, Illinois, offers a delightful blend of outdoor and family-friendly activities amidst beautiful scenery. Visitors can explore popular attractions such as beaches, urban parks, and nature preserves, making it an ideal destination for those seeking a vibrant city experience or a serene escape into nature. Whether you're travelling solo or with loved ones, Woodstock promises a memorable vacation filled with diverse experiences.

  1. Woodstock Square: This charming square is the heart of Woodstock, featuring historic architecture, unique shops, and local eateries. Its vibrant atmosphere provides a perfect spot for leisurely strolls and community events.
  2. McHenry County College: Located 9.7km away, this modern institution offers a dynamic educational environment. The campus is known for its engaging community events and cultural activities, showcasing local talent and creativity.
  3. McHenry County Fairgrounds: Situated within Woodstock, this venue hosts various outdoor events and fairs, perfect for families. Enjoy lively activities, rides, and local vendors, making it a fun destination for all ages.

Things to do recommended for families

Families visiting Woodstock, Illinois, can enjoy the natural beauty of Moraine Hills State Park, have fun at Brunswick Zone XL's arcade adventures, and explore the stars at Yerkes Observatory, all offering a fantastic blend of relaxation and excitement for everyone.

Things to do recommended for groups

Experience the charm of Woodstock by enjoying a performance at the historic Woodstock Opera House, hitting the greens at Craig Woods Golf Club, or shopping for unique finds at Crystal Court Shopping Center, located 14.5km away. Each venue offers a delightful mix of culture, sports, and family fun!

What do I need to keep in mind when booking a vacation in Woodstock

When planning your trip, whether you're traveling with a group, family, pets, or seeking extended stays, it's important to prioritize your preferences in your search. Here are some helpful booking tips for Vrbo to assist you.

  • Traveling to Woodstock with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily apply filters for all of these options, and more, on Vrbo.
  • Traveling to Woodstock with young kids: Traveling with young children can present its own set of challenges. It's important to prioritize their comfort and safety, as well as access to family-friendly amenities, like a private swimming pool. Additionally, considering how close you are to attractions that cater to families can enhance your travel experience.
  • Taking your pets with you to Woodstock: For many families, a getaway wouldn’t be the same without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that your entire family feels comfortably at home.
  • Planning for a long term stay visiting Woodstock: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using our filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like parking, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Woodstock

Woodstock, Illinois, offers a delightful vacation experience for families and outdoor enthusiasts alike. With its charming cottages and scenic locations, visitors can enjoy a friendly atmosphere that's perfect for budget-friendly getaways. Explore nearby towns and picturesque landscapes, where family-friendly activities abound. Whether you're looking for winter holiday rentals or simply want to soak in the welcoming vibes, Woodstock is a fantastic destination for creating cherished memories with loved ones.

  • Bull Valley: Located approximately 8.0km from Woodstock, Bull Valley is a picturesque city known for its stunning natural landscapes and outdoor activities. An ideal destination for sports enthusiasts, it boasts several golf courses and resorts that cater to both relaxation and recreation. Visitors can enjoy the serene surroundings, including a beautiful lake and inviting urban parks. Whether you’re looking to tee off at a local golf club or take a leisurely stroll by the beach, Bull Valley offers a tranquil escape into nature.
  • Crystal Lake: Situated around 12.9km from Woodstock, Crystal Lake is a vibrant city that enchants visitors with its scenic beauty and romantic atmosphere. The area is home to a variety of recreational spaces, including campgrounds and outdoor areas perfect for picnicking and leisurely walks. The expansive lake serves as a focal point, surrounded by lush greenery and a nearby national state park. Whether you’re enjoying a sunset by the water or exploring the trails, Crystal Lake is a perfect destination for couples and families alike.
  • Greenwood: Just 9.7km from Woodstock, Greenwood is a charming city that offers a family-friendly environment surrounded by stunning scenery. With its recreational areas and parks, families can enjoy a range of activities, from hiking to picnicking. The local lake and urban park provide ample opportunities for outdoor adventures and relaxation. Greenwood is a wonderful spot for those looking to connect with nature while enjoying quality time with loved ones.

Best time to go to Woodstock

If you're planning a trip to Woodstock, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January21.0°F (-6.1°C)Light RainMostly CloudyAverageAverage
February23.4°F (-4.8°C)Light RainMostly CloudyAverageSlightly Low
March36.1°F (2.3°C)Light RainMostly CloudyAverageSlightly Low
April46.2°F (7.9°C)Light RainMostly CloudyAverageSlightly Low
May58.3°F (14.6°C)Light RainMostly SunnyAverageAverage
June67.8°F (19.9°C)Light RainMostly SunnySlightly HighSlightly High
July72.0°F (22.2°C)Light RainMostly SunnySlightly HighSlightly High
August70.3°F (21.3°C)Light RainMostly SunnyAverageSlightly High
September63.9°F (17.7°C)Light RainMostly SunnySlightly HighAverage
October51.4°F (10.8°C)Light RainMostly SunnySlightly LowAverage
November38.5°F (3.6°C)Light RainMostly SunnySlightly LowAverage
December28.9°F (-1.7°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to search by price, location, and type of vacation rental. We're here to help you find the best options for your needs!

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, resume your previous arrangements, or manage your travel itinerary. You'll find your saved or booked properties neatly organized into categories: Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

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:

  • Bull Valley Golf Club (2 mi / 3.3 km)
  • Randall Oaks Golf Club (14.7 mi / 23.6 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)
  • Studio Winery (20 mi / 32.2 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:

  • Main Beach (7.8 mi / 12.6 km)
  • Crystal Lake Park (8 mi / 12.8 km)
  • McCullom Lake (8.9 mi / 14.4 km)
  • Petersen Park Beach (9.1 mi / 14.6 km)
  • McHenry Shores Beach Park (9.9 mi / 15.9 km)
  • Three Oaks Recreation Area (10 mi / 16.1 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 best area to stay in Woodstock when booking a vacation rental?
When considering a vacation rental in Woodstock, Illinois, one of the most appealing areas to stay is the charming downtown district. This vibrant neighbourhood boasts a delightful mix of historic architecture, boutique shops, and local eateries, creating a lively atmosphere for visitors. One of the key attractions in downtown Woodstock is the iconic Old Courthouse, famous for its stunning design and historical significance. Additionally, the area is home to the beautiful Woodstock Square, which often hosts various events and festivals, providing an excellent way to experience the local culture.

Another excellent option is the surrounding residential areas, such as the lovely West Side or the scenic East Side. These neighbourhoods offer a quieter, more suburban feel while still being conveniently located near the downtown attractions. In these areas, you can find numerous vacation rental properties that cater to different preferences, whether you're looking for a cosy cottage or a spacious family home. The proximity to both natural beauty and local amenities makes these areas great for enjoying a relaxing getaway in Woodstock.
How much does it cost to rent a vacation home in Woodstock?
Prices for vacation rentals 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. Vrbo offers something for every taste and budget, from affordable rentals in Woodstock to more spacious homes.
Are there any discounts for Woodstock vacation house rentals?
You can find great discounts on house rentals in Woodstock on Vrbo, 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.
What is the most popular type of vacation rental accomodation in Woodstock?
In Woodstock, vacation houses are the most popular type of rental accommodation, with several available throughout the area. These properties typically offer spacious living arrangements, featuring multiple bedrooms, fully equipped kitchens, and private outdoor spaces such as gardens or patios, ideal for relaxation after exploring the charming downtown or attending events at the historic Woodstock Opera House. The vacation houses provide a comfortable, home-like atmosphere, making them a great choice for families or groups looking to enjoy the local attractions and scenic surroundings.
Are there any family house rentals in Woodstock?
In Woodstock, Illinois, there are several family-friendly house rentals available, making it an excellent choice for families seeking a memorable getaway. The charming downtown area features historic architecture and offers a variety of activities for all ages, including the picturesque Woodstock Square, which is great for leisurely strolls and shopping.

Properties in this locale often come equipped with spacious living areas, fully stocked kitchens for preparing family meals, and outdoor spaces where children can play or families can enjoy a barbecue. Many homes also provide amenities such as Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable stay.
Can I rent a vacation home with a pool or hot tub in Woodstock?
In Woodstock, Illinois, there are several vacation homes available for rent that feature pools and hot tubs, making it an appealing destination for travellers seeking relaxation and comfort. The area is known for its charming historic town square and scenic surroundings, providing a lovely backdrop for a getaway.
Can I find long-stay vacation rentals in Woodstock?
A long-stay vacation rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Woodstock?
In Woodstock, there are several pet-friendly house rentals available, offering a range of amenities for travellers. Many of these properties feature spacious living areas, fully equipped kitchens, and outdoor spaces where pets can enjoy the fresh air. The charming neighbourhoods provide an inviting space, with some rentals conveniently located near local parks and recreational areas.

For those travelling with pets, the nearby Emricson Park is a delightful spot, featuring walking trails and open green spaces, ideal for leisurely strolls and playtime. Additionally, the historic downtown area of Woodstock offers pet-friendly cafes and shops, allowing visitors to explore the local culture without leaving their furry companions behind.
Are there any remote work vacation rentals in Woodstock?
In Woodstock, Illinois, there are several remote work vacation rentals available, making it a suitable destination for those looking to combine work and leisure. Many of these properties offer amenities tailored for remote professionals, such as dedicated office spaces, desk chairs, and reliable Wi-Fi, ensuring a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Woodstock vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals 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 on Vrbo 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.
What are popular rental amenities in Woodstock?
In Woodstock, popular rental amenities include kitchens, which are essential for preparing meals, along with dishwashers and microwaves for added convenience. Many properties also offer complimentary Wi-Fi, allowing guests to stay connected during their stay. Additionally, coffee makers are commonly found in the rentals, providing a great start to the day with a fresh brew.
When is the best time to visit Woodstock for a vacation rental?
July is the most popular time to visit Woodstock, Illinois, drawing in families and travellers eager to enjoy the vibrant summer atmosphere. During this peak season, from June to August, the town buzzes with energy, offering a variety of outdoor activities, including festivals, farmers' markets, and scenic river walks. The warm temperatures, typically ranging from the mid to high 20s Celsius, create a great setting for enjoying the lush parks and local attractions.

If you're planning to explore the charming downtown area or take part in the various summer events, July offers a lively experience, ideal for those who appreciate a bustling environment filled with fellow visitors. You can wander through unique shops, sample local cuisine, and immerse yourself in the community spirit that Woodstock is known for.

For those looking for a more budget-friendly option, consider visiting in December. Although it's a quieter time of year, the vacation season brings a unique charm to the town, with festive decorations and local events that create a warm and friendly space. You can enjoy a peaceful getaway while exploring the winter wonderland and perhaps even partake in seasonal activities.
How early should I book a Woodstock vacation rental?
Book your Woodstock vacation rental 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 Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Woodstock?
In Woodstock, Illinois, visitors can enjoy a variety of attractions that showcase the town's charm and history. The historic Woodstock Square is a focal point, featuring beautifully preserved architecture, quaint shops, and local eateries. Here, you can also find the iconic Old Courthouse, which has been a backdrop for films and events alike.

Nearby, the Woodstock Opera House hosts a range of performances and cultural events, making it a great spot for those interested in the arts. For nature enthusiasts, the beautiful Emricson Park offers walking trails, picnic areas, and a serene lake, great for leisurely afternoons.
Can I change or cancel my Woodstock home rental booking on Vrbo?
To find Woodstock vacation rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Woodstock vacation rental prices shown on Vrbo?
Vrbo 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.

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