Photo by Erik Rowley

Woodstock Holiday Rentals

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Holiday Rentals in Woodstock

Timber Ridge Lodge and Waterpark
3.5 star property
8.6 out of 10, Excellent, (2562)
"Love this place and I always stay with them. ❤️ highly recommended nice clean and quiet. "
The price is AU$297
includes taxes & fees
9 Dec - 10 Dec
Timber Ridge Lodge and Waterpark
Mill Creek Hotel
2.5 star property
9.2 out of 10, Wonderful, (1135)
"Friendly helpful staff, cute decor. Excellent breakfast."
The price is AU$216
includes taxes & fees
3 Dec - 4 Dec
Mill Creek Hotel
Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking
9.8 out of 10, Exceptional, (80)
"This place was amazing. Located right in the center of it all. Communication was easy and everything was in order. The accommodations were clean, neat and beautifully decorated. The deck outside is amazing. It was a little chilly (November) however during the sunny daytime hours we enjoyed sitting out on the deck. This location is so close to everything. We enjoyed our stay."
The price is AU$635
includes taxes & fees
26 Nov - 27 Nov
Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
10.0 out of 10, Exceptional, (56)
"Our dream is to one day own a home near a lake. We got a taste of it and definitely would like more of it. Cora Cottage on Fox Lake is just magical and magnificent. The moment we stepped in, we were mesmerized by the view and sounds of the water. In the house itself, you'll find yourself saying that it feels like home; clean, beautiful, and wonderful."
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Experience Stay at the Glamping Loft Lake Geneva |Group Stays |12 Stylish Tent Suites |Kitchen & Bar
10.0 out of 10, Exceptional, (26)
"Glamping Loft is a beautiful place for a ladies' getaway. The ambiance is warm and like a fairytale. It has everything you need if you want to bring in your own food and drinks or if you'd rather hit the town, Lake Geneva is right out the front door. I would definitely go back again. "
The price is AU$1,452
includes taxes & fees
25 Nov - 26 Nov
Experience Stay at the Glamping Loft Lake Geneva |Group Stays |12 Stylish Tent Suites |Kitchen & Bar
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
9.6 out of 10, Exceptional, (29)
"The spacious, well-maintained home was perfect for our group. The bedrooms were roomy, and the living areas provided plenty of space to relax and enjoy time together. The fully equipped kitchen made meal prep easy. A highlight was the neighboring estate with horses. The children loved it! The outdoor spaces were ideal for relaxation, with patios for morning coffee. Overall, this rental was the perfect setting for a memorable getaway. "
The price is AU$2,008
includes taxes & fees
26 Nov - 27 Nov
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna
9.2 out of 10, Wonderful, (7)
"The house was great. The pool temp was very warm when we arrived we did our best to cool it down. We really enjoyed the stay."
10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna
NEWLY Updated! Cove of Lake Geneva, Private Luxury Resort Pool View
9.0 out of 10, Wonderful, (94)
"The property was beautiful, great location for walking. Love the decor. The bed was so comfy. Thank you for a great anniversary! "
NEWLY Updated! Cove of Lake Geneva, Private Luxury Resort Pool View
Lake House Retreat Steps From Lake Geneva ~ Abbey Springs Resort!
9.8 out of 10, Exceptional, (111)
"What a great place for a family get away. We had 10 in the group and there were plenty of spaces to enjoy. We spent a lot of time on the screened in porch for morning coffee and evening cocktails. Fully equipped kitchen. Close to both beach and pool. The owner was very responsive and easy to work with. Would stay again. "
Lake House Retreat Steps From Lake Geneva ~ Abbey Springs Resort!
Historical Downtown Geneva Bungalow |Upper Unit |Parking for 3 |Walkable |Near Shops & Restaurants
10.0 out of 10, Exceptional, (52)
"Girls weekend for my co-worker, her daughters and infant grandson. They loved the location…it was close to everything. The home was clean and neat, and the host was amazing."
The price is AU$859
includes taxes & fees
29 Nov - 30 Nov
Historical Downtown Geneva Bungalow |Upper Unit |Parking for 3 |Walkable |Near Shops & Restaurants
Indoor Kidquariam, Large Group Equipped, EnglishPrairieBnB
10.0 out of 10, Exceptional, (35)
"Our family had a blast! Everyone from ages 4 months to 64 years old had a great time. This house was perfect for hosting a large multi-family gathering. Rainy weather did not ruin our trip since there was so much to do inside. The kids enjoyed the bounce house, the digital game table, board games, and of course the pool! The host went above and beyond with special touches including having burp cloths, a soothing noise machine, and a nursery room set up! They even had an extra place to put the...
The price is AU$1,870
includes taxes & fees
3 Dec - 4 Dec
Indoor Kidquariam, Large Group Equipped, EnglishPrairieBnB
Poolside Lookout at the Cove Hotel |Downtown Lake Geneva |Hot Tub |Walkable |Resort Game Room & Gym
8.8 out of 10, Excellent, (13)
"This condo was the perfect size for our family and great location to food and shopping. "
The price is AU$531
includes taxes & fees
26 Nov - 27 Nov
Poolside Lookout at the Cove Hotel |Downtown Lake Geneva |Hot Tub |Walkable |Resort Game Room & Gym
Lincoln Log Cabin · Elkhorn 3 Bedroom 2 Bathroom Log Cabin Sleeps 8
9.8 out of 10, Exceptional, (8)
"This place looked just as beautiful as the photos suggested, exuding tranquility and charm. However, we decided to check out early due to a few concerns. The living room lamp would unexpectedly turn off, and the lights, especially those illuminating the spiral staircase, would flicker occasionally. Our primary issue, though, was that our 2-year-old was fascinated by the spiral stairs. Unfortunately, they weren’t designed with little ones in mind, presenting a safety hazard that made us uneasy. "
The price is AU$604
includes taxes & fees
25 Nov - 26 Nov
Lincoln Log Cabin · Elkhorn 3 Bedroom 2 Bathroom Log Cabin Sleeps 8
Quaint Bungalow, near Great Lakes Naval Base
10.0 out of 10, Exceptional, (56)
"Got to stay in this wonderful home while visiting my son and his family. I loved it!"
The price is AU$486
includes taxes & fees
3 Dec - 4 Dec
Quaint Bungalow, near Great Lakes Naval Base
THE DOWNTOWNER....Largest House on Main St. 14 Beds, Sleeps 20
9.8 out of 10, Exceptional, (180)
"Perfect for big groups. Everything is within walking distance. Coffee, shopping, drinks, food, and so much more! Owner is very responsive. Thanks for sharing your home with us!"
THE DOWNTOWNER....Largest House on Main St. 14 Beds, Sleeps 20
Top location, a block from everything, no cleaning fee, Martini Suite
9.8 out of 10, Exceptional, (66)
"Great location! We were able to walk everywhere in town. The Martini suite was clean and had everything we needed. Would definitely go back! "
Top location, a block from everything, no cleaning fee, Martini Suite
Riverfront rental with fun activities
10.0 out of 10, Exceptional, (22)
"Great place, awesome host. Would definitely recommend. "
The price is AU$344
includes taxes & fees
17 Dec - 18 Dec
Riverfront rental with fun activities
Downtown Hideaway - Entire Building |Fun, Convienent & Comfortable |Sleeps 14 |1000+ 5 Star Reviews
9.8 out of 10, Exceptional, (15)
"This place is in a perfect location to everything. We didn’t have to drive anywhere. Very clean and immediate response from owners about questions we had. Would definitely stay there again!"
The price is AU$1,078
includes taxes & fees
26 Nov - 27 Nov
Downtown Hideaway - Entire Building |Fun, Convienent & Comfortable |Sleeps 14 |1000+ 5 Star Reviews
Ground- Level Lake Geneva Villa!
9.0 out of 10, Wonderful, (61)
"Great experience. "
The price is AU$594
includes taxes & fees
26 Nov - 27 Nov
Ground- Level Lake Geneva Villa!
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
9.4 out of 10, Exceptional, (95)
"We had a family crew of close to 20 people. We really enjoyed fishing off the pier, playing baseball in the big yard, kayaking out to the open lake, and just hanging out in the open kitchen/living room. Would recommend for big groups. Great host, quick responses."
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Woodstock you may be interested in

AmericInn by Wyndham Woodstock IL
2.5 star property
8.0 out of 10, Very good, (813)
"Easy to find, park, check-in and check out. Pleasant staff. Stay with no frills and the most basic of amenities. No security or surveillance in the parking area or corridors that we noticed, and there were different, individual men with open containers hanging around the outside entry at night. A local diner favorite is just across the parking lot if you’d like a hearty breakfast or meal. Fine. "
The price is AU$123
includes taxes & fees
3 Dec - 4 Dec
AmericInn by Wyndham Woodstock IL
Timber Ridge Lodge and Waterpark
3.5 star property
8.6 out of 10, Excellent, (2562)
"Love this place and I always stay with them. ❤️ highly recommended nice clean and quiet. "
The price is AU$297
includes taxes & fees
9 Dec - 10 Dec
Timber Ridge Lodge and Waterpark
Abbey Resort and Avani Spa
3.5 star property
8.4 out of 10, Very good, (1096)
"Everything was amazing!!!"
The price is AU$198
includes taxes & fees
22 Dec - 23 Dec
Abbey Resort and Avani Spa
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

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Frequently asked questions

Can I find holiday rentals in Woodstock?

Yes, there are holiday rentals in Woodstock close to McHenry County Fairgrounds, or you can select a more secluded option if you're looking for a relaxing stay. Woodstock is known for its shopping and jazz scene. Make sure you have time to check out the golf courses while you're in the area.

What are some of the best holiday rentals that Woodstock has to offer?

Big Family house close to everything!: This holiday home rental outside of Woodstock is located in the city centre, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Woodstock?

Choose from 4 Expedia holiday rentals in Woodstock for a memorable holiday.

What can I see and do in Woodstock?

Cultural attractions include Woodstock Opera House, whereas Emricson Park is a spot to enjoy nature. While here, Woodstock Square and McHenry County Fairgrounds are other places worth a visit.

What are holiday rentals like in Woodstock?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Woodstock. Holiday rentals offer extras such as patios, hot tubs and fire pits to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a small group gathering.