Woodstock Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Woodstock vacation rentals

Water park
Timber Ridge Lodge and Waterpark

Aparthotel in Lake Geneva

Timber Ridge Lodge and Waterpark
3.5 star property
8.6 out of 10, Excellent, (3065)
"Very nice room and fun waterpark. "
United States
Kristi
The price is ￥21,840
￥30,472 total
includes taxes & fees
Dec 14 - Dec 15
Timber Ridge Lodge and Waterpark
Indoor pool, sun loungers
Mill Creek Hotel

Aparthotel in Lake Geneva

Mill Creek Hotel
2.5 star property
9.2 out of 10, Wonderful, (1217)
"Enjoyed our stay, perfect location !"
United States
Lisa
The price is ￥24,381
￥27,673 total
includes taxes & fees
Dec 22 - Dec 23
Mill Creek Hotel
Interior
10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna

Vacation Home in Burlington

10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna
9.6 out of 10, Exceptional, (12)
"Very nice layout with lots of rooms and interesting places to be for a large group or family"
United States
Brian M.
10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna
Fridge, microwave, oven, stovetop
Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva

Vacation Home in Lake Geneva

Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva
2.0 star property
9.4 out of 10, Exceptional, (14)
"Had a great trip and the property was perfect for the 4 of us. Really appreciated the accessible shower."
United States
Bret S.
Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva
Indoor pool, a heated pool
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.

Vacation Home in Spring Grove

Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
10.0 out of 10, Exceptional, (15)
"Large house, indoor pool, plenty of space for families"
United States
Taylor S.
The price is ￥192,253
￥302,649 total
includes taxes & fees
Dec 11 - Dec 12
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
Smart TV, fireplace
Lakeside Loft! Updated 2 BR condo/Close to Lodge & GN/Outdoor Pool/Free Parking

Condo in Lake Geneva

Lakeside Loft! Updated 2 BR condo/Close to Lodge & GN/Outdoor Pool/Free Parking
10.0 out of 10, Exceptional, (6)
The price is ￥38,558
￥54,111 total
includes taxes & fees
Dec 11 - Dec 12
Lakeside Loft! Updated 2 BR condo/Close to Lodge & GN/Outdoor Pool/Free Parking
Exterior
THE ULTIMATE 6 BEDROOM LAKEHOUSE

Vacation Home in Lake Geneva

THE ULTIMATE 6 BEDROOM LAKEHOUSE
9.6 out of 10, Exceptional, (40)
"Wonderful house, perfect for a weekend stay. Great views and more than enough space?"
United States
John M.
The price is ￥112,169
￥182,566 total
includes taxes & fees
Dec 11 - Dec 12
THE ULTIMATE 6 BEDROOM LAKEHOUSE
Fridge, microwave, oven, stovetop
Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage

Vacation Home in Lake Geneva

Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage
9.8 out of 10, Exceptional, (109)
"Property was perfect for our group. We arrived to a clean home, everything was as advertised and hosts were very accommodating. Location was perfect, walking distance from downtown lake Geneva."
United States
David C.
Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage
A heated pool
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

Vacation Home in McHenry

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
9.2 out of 10, Wonderful, (41)
"The property management team, maintenance and cleaning staff are excellent. Communication was thorough and response time was quick. We enjoyed the pool very much."
United States
Allison K.
The price is ￥39,205
￥170,879 total
includes taxes & fees
Dec 11 - Dec 12
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
Property grounds
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!

Vacation Home in Burlington

Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
9.8 out of 10, Exceptional, (94)
"Hosts went above and beyond to accommodate my senior mother with a private bed on main level. They were also accommodating on other requests that I had. It was such a fun, nostalgic place. It was all exactly how I remembered the Old Mill to be and the private beach made for some additional family time. I see a wonderful future for this getaway place!! "
United States
Tina V.
The price is ￥70,569
￥141,787 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Smart TV, fireplace
Large Group Retreat w/ secluded party room and private pool

Vacation Home in Fox Lake

Large Group Retreat w/ secluded party room and private pool
7.8 out of 10, Good, (22)
"Place is in a state of disarray and should not be rented until repairs are made. Air conditioning is not functioning in the party room, heat on hot tub does not work, most chairs around the pool are broken, we had to buy toilet paper and paper towels, pots and pans in cabinets had not been washed and lights all over the house were out to include overhead lights in the kitchen. "
United States
Jack R.
Large Group Retreat w/ secluded party room and private pool
Smart TV, fireplace, DVD player, books
Private Beach & Pier Lake Front w/ Fireplace on Lake Como - Walk to Mars Resort!

Vacation Home in Lake Geneva

Private Beach & Pier Lake Front w/ Fireplace on Lake Como - Walk to Mars Resort!
10.0 out of 10, Exceptional, (318)
"Our family is always comfortable and well taken care of with quick responses to our questions by Ali. "
United States
Laura M.
Private Beach & Pier Lake Front w/ Fireplace on Lake Como - Walk to Mars Resort!
Outdoor dining
Private Country House near Lake Geneva, Como and Williams Bay

Vacation Home in Lake Geneva

Private Country House near Lake Geneva, Como and Williams Bay
10.0 out of 10, Exceptional, (94)
"Excellent bedrooms & baths. Cogregating areas large and well done."
United States
Gerald F.
Private Country House near Lake Geneva, Como and Williams Bay
Dining
#EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms

Vacation Home in Twin Lakes

#EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms
10.0 out of 10, Exceptional, (42)
"Wonderful place and wonderful host!!!"
United States
Catherine C.
#EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms
Fridge, microwave, oven, stovetop
Quaint, quiet condo minutes from Lake Geneva

Condo in Lake Geneva

Quaint, quiet condo minutes from Lake Geneva
9.6 out of 10, Exceptional, (34)
"Our family had a great time staying here. Our daughter loved playing with the toys. We were happy to have all the extras that we needed there for our daughter. Location was great and pool was awesome. Host was easy to contact and very helpful. "
United States
Lisa D.
The price is ￥19,630
￥49,855 total
includes taxes & fees
Dec 11 - Dec 12
Quaint, quiet condo minutes from Lake Geneva
TV, video games, DVD player, foosball
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲

Vacation Home in Richmond

🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
9.4 out of 10, Exceptional, (110)
"Perfect for hosting a big family party and great space for a getaway! The host helped us with a boat rental and the house was well-stocked with towels and kitchen/bathroom essentials as well as water toys to use on the lake! We had a blast! "
United States
Ashley F.
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
Smart TV, fireplace, video games, foosball
Luxury Lake Geneva cottage w/ sauna + hot tub + geodesic dome on 2-acres

Cottage in Delavan

Luxury Lake Geneva cottage w/ sauna + hot tub + geodesic dome on 2-acres
9.6 out of 10, Exceptional, (45)
"Stayed with a group of 14 for the weekend - property has a little bit of everything you could need while being close to downtown Lake Geneva and Delavan!"
United States
Justin S.
Luxury Lake Geneva cottage w/ sauna + hot tub + geodesic dome on 2-acres
Terrace/patio
Harbor & Hearth a Modern Lakefront Condo w/ Pool, Spa & Dining On The Lake

Condo in Lake Geneva

Harbor & Hearth a Modern Lakefront Condo w/ Pool, Spa & Dining On The Lake
9.0 out of 10, Wonderful, (70)
"Loved the location and accessibility to so many things. Everything we needed was there. Thank you"
United States
Jane Burden B.
The price is ￥17,642
￥42,578 total
includes taxes & fees
Dec 11 - Dec 12
Harbor & Hearth a Modern Lakefront Condo w/ Pool, Spa & Dining On The Lake
Property grounds
🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲

Vacation Home in Twin Lakes

🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲
9.2 out of 10, Wonderful, (57)
"We had a great time! Jeff was easy to communicate with and accommodating to our group. While the property is beautiful, folks should know you cannot swim at the dock. We did rent a pontoon which provided lots of swimming opportunity and fun! Thanks again for a great stay!"
United States
Kelsey H.
🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲
Outdoor dining
Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking

Vacation Home in Lake Geneva

Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking
9.8 out of 10, Exceptional, (96)
"This property’s location can’t be beat! The balcony patio is incredible, the beds were comfortable, the ac kept us cool during a very hot and humid weekend, and the kitchen was stocked with plenty of plates, mugs, etc. We would stay here again. "
United States
Emily P.
The price is ￥15,577
￥67,080 total
includes taxes & fees
Dec 17 - Dec 18
Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking
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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Top Woodstock Hotel Reviews

DoubleTree by Hilton Libertyville - Mundelein

DoubleTree by Hilton Libertyville - Mundelein

10/10 Excellent
"I checked in I slept the bed was comfy."
Mark 1-night trip
Posted 2 days ago
DoubleTree by Hilton Libertyville - Mundelein

Find out more about Woodstock

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 vacation rentals in Woodstock?

Yes, we offer vacation rentals in Woodstock close to McHenry County Fairgrounds, or you can choose a more remote option if you're looking for extra privacy while you relax. 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 vacation home rentals that Woodstock has to offer?

Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!: Visitors like this Woodstock vacation home rental. It is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Woodstock?

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

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 Woodstock City Hall are other places worth a visit.

What are vacation rentals like in Woodstock?

Vacation rentals are privately owned accommodations you can reserve for several days or more in Woodstock. Vacation rentals feature extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.