Woodstock Holidays from AU$808
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Your Woodstock Holiday
There's plenty to like about Woodstock, from its rich history to its spectacular views and beyond. When you're ready to spend a bit of time in this fascinating city, our Woodstock holiday packages are calling your name. Like to explore your surroundings? McHenry County Courthouse, McHenry County College and Bull Valley Golf Club are among the top-rated places to visit during a trip to Woodstock. Whoever you're travelling with and whatever your bank balance, your dream Woodstock holiday is just a few clicks away with Expedia.
The Latest Woodstock Holiday Deals
Price found within the past 48 hours. Click for updated prices.
The Drake
Downtown Chicago
Price was AU$1,183, price is now AU$808 per person
AU$808
per person
16 Nov - 19 Nov
found 20 hours ago
Return flight included
Greensboro (GSO) to Chicago (ORD)
8.8/10 Excellent! (1,291 reviews)
Great location and wonderful staff. Stayed with my family of four and we were able to easily get to all the wonderful sites we wanted to visit. The historic charm and lastige spaces enhanced our stay and our breakfast was superb.
Reviewed on 14 Oct 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$1,974, price is now AU$1,358 per person
AU$1,358
per person
16 Nov - 19 Nov
found 20 hours ago
Return flight included
Raleigh (RDU) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in.
Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better.
Reviewed on 14 Oct 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was AU$2,045, price is now AU$1,417 per person
AU$1,417
per person
16 Nov - 19 Nov
found 20 hours ago
Return flight included
Greensboro (GSO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel.
Reviewed on 15 Oct 2025
Pendry Chicago
Downtown Chicago
Price was AU$1,417, price is now AU$1,025 per person
AU$1,025
per person
16 Nov - 19 Nov
found 20 hours ago
Return flight included
Greensboro (GSO) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.
Reviewed on 11 Oct 2025
Woodstock Holiday
Woodstock Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 25,200 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Main Beach, Woodstock Opera House and McHenry Shores Beach Park |
Our pick of the best Woodstock Hotel Deals
AmericInn by Wyndham Woodstock IL
990 Lake Avenue, Woodstock, IL
Fully refundableReserve now, pay when you stay
The price is AU$138 per night from 19 Oct to 20 Oct
AU$138
19 Oct - 20 Oct
includes taxes & fees
7.8/10 Good! (952 reviews)
"Very nice room for what we paid. Staff was courteous. Breakfast bar was stocked well. Clean pool. Room was well maintained. Only real complaint was the very low water pressure in the shower."
Reviewed on 5 Oct 2025
Quality Inn & Suites Woodstock near Lake Geneva
1785 S Eastwood Dr, Woodstock, IL
Fully refundableReserve now, pay when you stay
The price is AU$115 per night from 19 Oct to 20 Oct
AU$115
19 Oct - 20 Oct
includes taxes & fees
5.8/10 (271 reviews)
"It was a relaxing stay. Just what I needed. Thank you."
Reviewed on 16 Sept 2025
Super 8 by Wyndham Woodstock
1220 Davis Rd, Woodstock, IL
Fully refundableReserve now, pay when you stay
The price is AU$109 per night from 26 Oct to 27 Oct
AU$109
26 Oct - 27 Oct
includes taxes & fees
6.2/10 (520 reviews)
"B"
Reviewed on 10 Oct 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
