Photo by Erik Rowley

Woodstock Holiday Rentals

Save an average of 15% on thousands of properties with Expedia Rewards

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide

Holiday Rentals in Woodstock

Property grounds
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
10.0 out of 10, Exceptional, (36)
"Home is exactly as listed and pictures are accurate for a peaceful getaway. Great view and quiet. Very clean, comfy bed. Owner was kind enough to mail back an item I had left behind."
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Terrace/patio
Get lost from the hustle. Peaceful nature, country living at its finest.
10.0 out of 10, Exceptional, (16)
"Owners make sure you have everything necessary!"
Get lost from the hustle. Peaceful nature, country living at its finest.
Fridge, microwave, oven, stovetop
Downtown Geneva Street Bungalow - Upper
10.0 out of 10, Exceptional, (42)
"my mom and I stayed with my 1.5 year old daughter for a night in LG and it was perfect! Didnt have to use the car once, easy to park and check in. clean and very cute! thanks for having us!"
Downtown Geneva Street Bungalow - Upper
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Fridge, microwave, oven, stovetop
Cozy Woodland Cabin, pet-friendly and fenced in yard.
10.0 out of 10, Exceptional, (11)
"This is wonderful place to stay, just a few blocks from the lake, and with a wonderful fenced-in back yard with ample outdoor furniture."
Cozy Woodland Cabin, pet-friendly and fenced in yard.
Exterior
Big Family house close to everything!
10.0 out of 10, Exceptional, (159)
"What a lovely experience! Host was helpful and responsive. House is large and well appointed, perfect for our group of families. Kids had a few spots to play and have a safe “sleepover” experience. Lots of space to lounge, play and eat. It’s winter so we didn’t get to enjoy the outdoor space, but we talked about wanting to come back and enjoy the yard and short walk to the lake and all the amenities of downtown. The rooms are perfect for a large group, with 5 of the well-sized bedrooms being en...
Big Family house close to everything!
Exterior
Indoor Kidquariam, Large Group Equipped, EnglishPrairieBnB
10.0 out of 10, Exceptional, (32)
"This house has everything you need for a great getaway! It was clean, very well-appointed, and had lots of space to spread out. The beds were comfy, the coffee bar was well stocked, and there was even a station set up with waffle mix, makers, and fixins'. Mike (property owner) responded quickly to our questions and Carrie (property manager) was delightful! There is a reason this place has so many glowing reviews...HIGHLY RECOMMEND!"
Indoor Kidquariam, Large Group Equipped, EnglishPrairieBnB
TV, books
Quaint Bungalow, near Great Lakes Naval Base
10.0 out of 10, Exceptional, (45)
"This is one of the most charming vrbo that i have stayed at. the house is just as 1 described My son graduated Navy Bootcamp and it was so nice to have the comfort of this home vs sharing 3 hotel rooms."
The price is HK$1,055
HK$2,414 total
includes taxes & fees
8 May - 9 May
Quaint Bungalow, near Great Lakes Naval Base
Pool
Riverfront rental with fun activities
10.0 out of 10, Exceptional, (15)
"Lots of sleeping options. Fully furnished cute house"
The price is HK$1,367
HK$1,967 total
includes taxes & fees
6 May - 7 May
Riverfront rental with fun activities
Fridge, microwave, oven, stovetop
Large Lakefront Home on Lake Como - Private Pier!
10.0 out of 10, Exceptional, (188)
"Extremely nice if the water wasn't choppy it would have been a perfect day weekend still love it"
Large Lakefront Home on Lake Como - Private Pier!
Property grounds
Downtown Hideaway- Entire Building
10.0 out of 10, Exceptional, (7)
"We rented both floors of this unit in Lake Geneva. The property itself is spacious, tidy, showers have great water pressure. Beds were comfortable, and the decor was fun. The location is incredibly convenient to restaurants and shops. We even walked to the Lake Geneva Museum two blocks away. We would definitely rent this unit again!"
The price is HK$2,578
HK$6,993 total
includes taxes & fees
6 May - 7 May
Downtown Hideaway- Entire Building
Fridge, microwave, oven, stovetop
THE DOWNTOWNER....in the heart of Lake Geneva!
10.0 out of 10, Exceptional, (162)
"The Downtowner couldn't have been more perfect for our group. We loved the outdoor area and the ease of getting around downtown LG. Everyone was pleased with the house and would come back again. Having a bathroom in almost all bedrooms was a major perk and we appreciated there being 2 refrigerators as well."
THE DOWNTOWNER....in the heart of Lake Geneva!
Fridge, microwave, stovetop, dishwasher
Renovated Lake Geneva Home Near Dtwn + Beach!
10.0 out of 10, Exceptional, (12)
"There were six adults staying for winter realm for the weekend. We also had our dogs. Communication was excellent. House had everything we needed. Fenced in yard was a plus for the dogs."
Renovated Lake Geneva Home Near Dtwn + Beach!
Fridge, microwave, oven, stovetop
2 Bedroom Apartment Walking distance to downtown Lake Geneva
10.0 out of 10, Exceptional, (37)
"Sue was a great host. She was great about communicating the check in and check out instructions. She left us a thoughtful note, gift card, and bottle of wine. The home was very clean and it was the perfect place to stay when visiting Lake Geneva."
2 Bedroom Apartment Walking distance to downtown Lake Geneva
Property grounds
Stunning Lakefront Home on the Chain O'Lakes! ★ Amazing Views & Newly Rehabbed
10.0 out of 10, Exceptional, (62)
"Beautiful, spectacular mornings with the sunrise and the view of the lake. The house is very comfortable. The kitchen is very nice. We were able to prepare all our family meals."
Stunning Lakefront Home on the Chain O'Lakes! ★ Amazing Views & Newly Rehabbed
Bathroom
comfortably sleeps 10 guests
10.0 out of 10, Exceptional, (25)
"Excellent for a small group of people to get away and spend a long weekend knitting, crocheting, spinning and weaving. Spacious enough for everyone. Charming old building with well done updates."
The price is HK$1,172
HK$3,289 total
includes taxes & fees
6 May - 7 May
comfortably sleeps 10 guests
Property grounds
Geneva Beach House "Como" Suite. Walk to lake!
10.0 out of 10, Exceptional, (19)
"Property was cozy and had great access to all areas of Lake Geneva."
The price is HK$859
HK$2,332 total
includes taxes & fees
6 May - 7 May
Geneva Beach House "Como" Suite. Walk to lake!
Beach
Across the street from the beach. In the heart of Lake Geneva!
9.8 out of 10, Exceptional, (70)
"Cute little place with awesome views of the lake!!! All the amenities needed, very nicely decorated, and comfy beds! Personal parking spot a great plus! Some maintenance required though and a funny smell that was not pleasant to come back to. We had to buy a candle to drown out the smell and one family member with autoimmune health struggles had difficultly with this."
The price is HK$3,437
HK$6,574 total
includes taxes & fees
6 May - 7 May
Across the street from the beach. In the heart of Lake Geneva!
A heated pool
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
9.8 out of 10, Exceptional, (24)
"The house is so big and beautiful, and we enjoyed our weekend staying there, thank you."
The price is HK$5,546
HK$12,707 total
includes taxes & fees
8 May - 9 May
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
Fridge, microwave, oven, stovetop
A block from Lake Geneva and downtown, Martini Suite
9.8 out of 10, Exceptional, (50)
"The listing and photos are exactly what you get in this fun and different property. The location was perfect for walking to various restaurants and other sites. We were even just a few minutes' walk to the lake path entrance for a nice hike partway around the lake. Our suite was cozy with an actual full bar (minus the liquor) in the room. We were able to watch the NCAA playoffs on the big screen TV over the bar, just like a real sports bar. The room comes with access to a lovely balcony that...
A block from Lake Geneva and downtown, Martini Suite
Terrace/patio
6 bd Country Estate on 28 Acres near Lk Geneva w/ Ponds, Trails, Fenced Dog-park
9.8 out of 10, Exceptional, (16)
"The property is a gem. We wished the weather was better so we could enjoy time outside however the briskness of fall had arrived. We were constrained to the inside of the house which is very artistic with an interesting layout. The house was a bit tricky for the amount of guests we had for privacy. There were about 10 of us however two of the bathrooms did not have doors. Although these bathrooms have an extremely beautiful views, the missing doors were an issue. The only other problem were all...
6 bd Country Estate on 28 Acres near Lk Geneva w/ Ponds, Trails, Fenced Dog-park
Don't see what you're looking for?
See all available properties in Woodstock
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.

Other types of properties in Woodstock you may be interested in

Terrace/patio
The Ridge Hotel
4.0 star property
9.0 out of 10, Wonderful, (1003)
"."
The price is HK$857
HK$1,143 total
includes taxes & fees
6 May - 7 May
The Ridge Hotel
Water park
Timber Ridge Lodge and Waterpark
3.5 star property
8.6 out of 10, Excellent, (2275)
"We loved the indoor water park. We enjoyed the jacuzzi-style bath tub in the hotel room bathroom. The bedding provided for the sofa bed could have been better but you can call for room service for this. The kitchen in the room is very convenient. Breakfast at the hotel was convenient, but a bit overpriced. I would encourage the property to discount their food or provide free breakfast, to give guests greater value. These things would bring me back more frequently."
The price is HK$991
HK$1,372 total
includes taxes & fees
20 May - 21 May
Timber Ridge Lodge and Waterpark
Couples treatment room(s), sauna, hot tub, steam room, body treatments
Abbey Resort and Avani Spa
3.5 star property
8.4 out of 10, Very good, (1006)
"Great resort close to marina and Lake Geneva "
The price is HK$757
HK$960 total
includes taxes & fees
12 May - 13 May
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.

Search for holiday rentals in Woodstock on Expedia! You can easily find your home rentals, villas, holiday apartments in Woodstock using one of the methods below:

  • View our selection of featured holiday rentals in Woodstock
  • Use the map to find apartments and other holiday homes in the Woodstock neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Woodstock while they last

Look no further and take a look at our great range of rental properties in Woodstock!

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.

Recent reviews of Woodstock properties
Expedia verified reviews

Abbey Resort and Avani Spa

Abbey Resort and Avani Spa

5/5 Excellent
"Great resort close to marina and Lake Geneva "
A verified traveller stayed at Abbey Resort and Avani Spa
Posted 2 days ago
Abbey Resort and Avani Spa