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Woodstock Holiday Rentals

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Check prices for these dates

Tonight
25 Aug - 26 Aug
Tomorrow
26 Aug - 27 Aug
This weekend
29 Aug - 31 Aug
Next weekend
5 Sept - 7 Sept

Holiday Rentals in Woodstock

Timber Ridge Lodge and Waterpark
Water park

Timber Ridge Lodge and Waterpark

3.5 star property
8.6 out of 10, Excellent, (2967)
"Nice stay for a short weekend getaway. "
The price is HK$1,147
HK$1,575 total
includes taxes & fees
23 Sept - 24 Sept
Timber Ridge Lodge and Waterpark
Mill Creek Hotel
Indoor spa tub

Mill Creek Hotel

2.5 star property
9.2 out of 10, Wonderful, (1194)
"We had another nice stay. The staff are friendly, and they even made a birthday sign and balloons for me."
The price is HK$1,661
HK$1,885 total
includes taxes & fees
1 Sept - 2 Sept
Mill Creek Hotel
Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking
Beach

Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking

9.8 out of 10, Exceptional, (91)
"A few wonderful days spent with family in a welcoming home. I must have experienced this again."
The price is HK$1,883
HK$4,881 total
includes taxes & fees
2 Sept - 3 Sept
Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking
Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage
Fridge, microwave, oven, stovetop

Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage

9.8 out of 10, Exceptional, (104)
"Out bachelor party stay was fantastic, everything about the trip was a breeze! "
Sleeps 20! DOWNTOWN LAKE GENEVA Fully Licensed 4 Bedrm House & 2 Bedrm Cottage
THE DOWNTOWNER....Largest House on Main St. 14 Beds, Sleeps 20
Fridge, microwave, oven, stovetop

THE DOWNTOWNER....Largest House on Main St. 14 Beds, Sleeps 20

9.8 out of 10, Exceptional, (189)
"I booked this property for a bachelorette party and everyone had a great time! It is in the perfect location for being able to walk to everything, which was perfect for a large group! The kitchen/living room space was perfect for all the girls to hang out together and play games. Parking is very limited, but there is a free lot nearby that we were able to utilize as well. "
THE DOWNTOWNER....Largest House on Main St. 14 Beds, Sleeps 20
Lakefront Haven: Waterfront Oasis with Dock, Spacious Swim Pier & Pano Lake view
6 bedrooms, desk, iron/ironing board, travel cot

Lakefront Haven: Waterfront Oasis with Dock, Spacious Swim Pier & Pano Lake view

2.5 star property
10.0 out of 10, Exceptional, (8)
"The house was amazing; the owner went above and beyond helping with all of our questions. The views were amazing. We can't wait to go back. "
Lakefront Haven: Waterfront Oasis with Dock, Spacious Swim Pier & Pano Lake view
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
A heated pool

HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub

9.4 out of 10, Exceptional, (39)
"The house was very clean and spacious. A lot of activities to do "
The price is HK$3,032
HK$9,825 total
includes taxes & fees
26 Aug - 27 Aug
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva
Fridge, microwave, oven, stovetop

Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva

2.0 star property
9.4 out of 10, Exceptional, (11)
"Had a great trip and the property was perfect for the 4 of us. Really appreciated the accessible shower."
Charming 3-bedroom house with WiFi and AC in lovely Lake Geneva
Private Country House near Lake Geneva, Como and Williams Bay
Outdoor dining

Private Country House near Lake Geneva, Como and Williams Bay

10.0 out of 10, Exceptional, (89)
"Good place to stay nice location "
Private Country House near Lake Geneva, Como and Williams Bay
Cozy RV in our land with community private beach, fire pit, bring your boat.
Property grounds

Cozy RV in our land with community private beach, fire pit, bring your boat.

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a nice time visiting Antioch, IL. The property clean, quiet and well maintained. The camper was adorable and very comfortable. Thank you!"
Cozy RV in our land with community private beach, fire pit, bring your boat.
10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna
Indoor pool, a heated pool

10,000 Sq. Ft. Home on 15 hunting acres with an in-door pool and sauna

9.4 out of 10, Exceptional, (10)
"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
Chic 3 bedroom Get-a-way in downtown Lake Geneva
Fridge, microwave, oven, stovetop

Chic 3 bedroom Get-a-way in downtown Lake Geneva

9.6 out of 10, Exceptional, (4)
"Nice place...was perfect for our family."
The price is HK$1,934
HK$2,515 total
includes taxes & fees
2 Sept - 3 Sept
Chic 3 bedroom Get-a-way in downtown Lake Geneva
Experience Stay at the Glamping Loft Lake Geneva |Group Stays |Stylish Tent Suites |Kitchen & Bar
Interior

Experience Stay at the Glamping Loft Lake Geneva |Group Stays |Stylish Tent Suites |Kitchen & Bar

10.0 out of 10, Exceptional, (30)
"We came to Wisconsin for a bachelorette party! This place was described perfectly and was absolutely perfect for our girls! We are very very pleased and would recommend this highly!"
The price is HK$1,539
HK$6,435 total
includes taxes & fees
2 Sept - 3 Sept
Experience Stay at the Glamping Loft Lake Geneva |Group Stays |Stylish Tent Suites |Kitchen & Bar
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
Outdoor dining

Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.

10.0 out of 10, Exceptional, (9)
"We enjoyed our stay at the house. The open spaces and high ceilings made the space feel special. Would love to reserve the space again in the future."
The price is HK$8,160
HK$13,667 total
includes taxes & fees
27 Aug - 28 Aug
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
Large Group Retreat w/ secluded party room and private pool
Fridge, microwave, oven, stovetop

Large Group Retreat w/ secluded party room and private pool

8.0 out of 10, Very good, (20)
"This property is better than advertised, it was exactly what we were hoping for. Pool area is awesome, all of the teenage boys LOVED the clubhouse, plenty of space to host. Communication with JJ was awesome. Would book again in a heartbeat and will have more stays there."
Large Group Retreat w/ secluded party room and private pool
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Terrace/patio

Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!

9.8 out of 10, Exceptional, (88)
"We loved the beach the kids could have stayed there all day! Fishing was wonderful too! Such a fun house!"
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
NEWLY Updated! Cove of Lake Geneva, Private Luxury Resort Pool View
Fridge, microwave, stovetop, dishwasher

NEWLY Updated! Cove of Lake Geneva, Private Luxury Resort Pool View

9.0 out of 10, Wonderful, (102)
"Great location! "
The price is HK$2,337
HK$3,797 total
includes taxes & fees
29 Aug - 30 Aug
NEWLY Updated! Cove of Lake Geneva, Private Luxury Resort Pool View
#EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms
Dining

#EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms

10.0 out of 10, Exceptional, (40)
"Even better than described"
#EnglishPrairieBnB - 8 Bedroom - 4.5 Bathrooms
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Dining

Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

10.0 out of 10, Exceptional, (84)
"Was here for a funeral. Good place to stay and relaxing."
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Walk to downtown/beach Huge historic house perfect for large groups or families
Terrace/patio

Walk to downtown/beach Huge historic house perfect for large groups or families

10.0 out of 10, Exceptional, (26)
"The home is as lovely as described. Very spacious, clean, and great location. We enjoyed our stay very much."
The price is HK$3,404
HK$6,880 total
includes taxes & fees
7 Sept - 8 Sept
Walk to downtown/beach Huge historic house perfect for large groups or families
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

Find out more about Woodstock

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!

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Wrigley Beach House |Great Views of Lake |2nd Floor |Balcony |Steps to Beach & Shopping |Parking: This holiday home rental outside of Woodstock is located on a lake, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Woodstock?

Choose from 3 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.