
Holiday houses in Woodstock
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Top-rated holiday rentals in Woodstock
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Woodstock holiday rentals
Other great holiday rentals in Woodstock
Top Guest favourite

Home in Twin Lakes
5 out of 5 average rating, 9 reviewsCozy Cabin in Town | Walk to Lake Mary
DavidRating, 5 stars3 days ago
We had a great stay. The house was perfect for a quick weekend getaway. We enjoyed some of the local spots in Twin Lakes and made the short drive for dinner in Lake Geneva. Highly recommend!
Guest favourite

Private room in Woodstock
4.93 out of 5 average rating, 395 reviewsMini Suite in the House of Odd
CraigRating, 5 stars1 week ago
The House of ODD is a truly unique and memorable experience. The space is full of personality, creativity, and thoughtful details that make it stand out. Matthew was very responsive and accommodating throughout—his communication made everything smooth from start to finish. Overall, a great experience. If you're looking for something out of the ordinary, this is the place.
Guest favourite

Cottage in Harvard
4.91 out of 5 average rating, 11 reviewsPeaceful Harvard Vacation Rental: 3 Mi to Town!
BonnieRating, 5 stars7 months ago
This cottage was a perfect place for long term intensive physical therapy. The kitchen was well-equipped for us to do our own meals, the washer and dryer were a plus, there was a comfortable sitting area and wifi to handle zoom calls and a well-maintained yard/garden/patio to enjoy. A great balance of privacy and connection with the owners and their pup. Highly recommend this place!!
Guest favourite

Private room in Crystal Lake
4.89 out of 5 average rating, 155 reviewsMaster Bedroom w/Bathroom - safe and cozy
ReneRating, 5 stars1 week ago
This was my third stay - it’s an awesome place and I felt right at home. Highly recommend!
Guest favourite

Private room in Cary
4.93 out of 5 average rating, 165 reviewsCasa de Cary 1 (private driveway/entrance/wifi)
BrianRating, 5 stars4 months ago
What a wonderful place to stay. Everything was fantastic, the bed the TV and cozy warm room. They went out of their way to make sure my entrance and driveway was snow free. would love to stay again soon.
Top Guest favourite

Private room in Woodstock
5 out of 5 average rating, 68 reviewsHot Tub Spa Suite! Mardi Gras House
AmandaRating, 5 stars1 week ago
Craig made sure we had everything we needed. He is super nice and his restaurant recommendations were spot on! Book here if you want to stay at a very cool and unique place!
Guest favourite

Hotel room in Rosemont
4.92 out of 5 average rating, 273 reviewsRelaxing Standard Room l Free Airport Shuttle
AlexeiRating, 5 stars2 weeks ago
easy check-in, super clean, friendly staff. parking is easy and affordable. will definitely be staying again!

Home in Woodstock
5 out of 5 average rating, 4 reviewsWater front ranch house
EvalRating, 5 stars10 months ago
We enjoyed our stay at Antonio's lovely home. It had all the comforts of home and more. I would most certainly recommend this home to anyone looking for peace and relaxation while on vacation.
Quick stats about holiday rentals in Woodstock
Total rentals
30 properties
Total number of reviews
1.5K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
20 properties include access to Wi-Fi
Popular amenities
Gym, BBQ grill and Laptop-friendly workspace
Destinations to explore
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- Wrigley Field
- United Center
- Six Flags Great America
- Humboldt Park
- Alpine Valley Resort
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Geneva National Resort & Club
- Lincoln Park Zoo
- Wicker Park
- Illinois Beach State Park
- Brookfield Zoo
- The 606
- Racine North Beach
- Grand Geneva Resort & Spa
- Moraine Hills State Park
- Richard Bong State Recreation Area
- Wilmot Mountain Ski Resort
- Medinah Country Club
- Skokie Country Club
- Raging Waves Waterpark
- Chicago Golf Club
- Four Lakes Alpine Snowsports
- Hurricane Harbor Rockford