Deals on vacations and trips to Woodstock

Save when you book Woodstock package deals

Choose two or more items and save on your trip:

Woodstock flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 13 - Aug 18
Roundtrip flight included
Raleigh (RDU) to Chicago (ORD)
This hotel features a restaurant, a coffee shop, and free WiFi in public areas. A 24-hour business center, express check-out, and dry cleaning are also on offer.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 25 - Jul 28
Roundtrip flight included
Newark (EWR) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 23 - Jun 29
Roundtrip non-stop flight included
Newark (EWR) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 24 - Jul 28
Roundtrip flight included
Newark (EWR) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this historic hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.
Ambassador Chicago, part of JdV by Hyatt

Ambassador Chicago, part of JdV by Hyatt

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 25 - Jul 30
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A coffee shop, a snack bar/deli, and a lobby fireplace are also on offer.

Top Woodstock hotel deals

AmericInn by Wyndham Woodstock IL

AmericInn by Wyndham Woodstock IL

2.5 out of 5
990 Lake Avenue, Woodstock, IL
Free Cancellation
Reserve now, pay when you stay
The price is $90 per night
$90
per night
May 26 - May 27
A casino, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the indoor pool and free perks like continental breakfast and free self parking.
Pet friendly
Breakfast included
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way, Lake Geneva, WI
Free Cancellation
Reserve now, pay when you stay
The price is $169 per night
$169
per night
May 27 - May 28
This smoke-free aparthotel features a golf course, free water park access, and a full-service spa. Take advantage of ski lessons, ski rentals and ski storage on site, and enjoy downhill skiing. Bring the family and enjoy the mini golf, children's pool, and kid-friendly dining.
Hot Tub
Fireplace
Abbey Resort and Avani Spa

Abbey Resort and Avani Spa

3.5 out of 5
269 Fontana Boulevard, Fontana, WI
Free Cancellation
Reserve now, pay when you stay
The price is $144 per night
$144
per night
May 27 - May 28
This smoke-free resort features a full-service spa, a marina, and 2 restaurants. Bring the family and enjoy the waterslide, arcade/game room, and kid-friendly dining. Enjoy the 2 spa tubs and get free self parking.
Hot Tub
Breakfast available
The Ridge Hotel

The Ridge Hotel

4 out of 5
W4240 WI-50, Lake Geneva, WI
Free Cancellation
Reserve now, pay when you stay
The price is $101 per night
$101
per night
May 27 - May 28
This resort features a restaurant, an indoor pool, and a bar/lounge. You'll appreciate the gym, poolside bar, and concierge services.
Pet friendly
Breakfast available
Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr, Lake Geneva, WI
Free Cancellation
Reserve now, pay when you stay
The price is $149 per night
$149
per night
May 28 - May 29
This hotel features an outdoor pool, an indoor pool, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Parking included
Country Inn & Suites by Radisson, Hoffman Estates, IL

Country Inn & Suites by Radisson, Hoffman Estates, IL

3 out of 5
2280 Barrington Rd, Hoffman Estates, IL
Free Cancellation
The price is $77 per night
$77
per night
May 29 - May 30
This hotel features a seasonal outdoor pool and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and airport shuttle. Free perks include buffet breakfast, free self parking, and an area shuttle.
Pet friendly
Breakfast included
Don't see what you're looking for?
See all available properties in Woodstock
View all properties
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.

Popular places to visit

Image for Woodstock Opera House

Woodstock Opera House

4.5/5(6 reviews)

You can enjoy a show at Woodstock Opera House during your trip to Woodstock. While you're in the area, stroll along the lakeside.

Woodstock Opera House
Image for Woodstock Square

Woodstock Square

4/5(19 reviews)

You can find out about the history of Woodstock with a trip to Woodstock Square. While you're in the area, stroll along the lakeside.

Woodstock Square
Image for McHenry County Fairgrounds

McHenry County Fairgrounds

Enjoy an outing to McHenry County Fairgrounds during your stay in Woodstock. While you're in the area, stroll along the lakeside.

McHenry County Fairgrounds

Frequently asked questions

How much are vacation packages to Woodstock?
Packages, which provide both flights and hotels in Woodstock, are priced from as little as $473. Turn your travel fantasies into reality and secure your trip with Travelocity today.
How long should my Woodstock vacation be?
An average of 2 nights is how long most people spend exploring the sights and sounds of Woodstock. Not sure if that’ll be sufficient time to tick everything off your must-see list? Stay a couple more nights and experience everything this place has to offer.
Where can I get the best vacation package deals for Woodstock?
Grabbing a great package deal to Woodstock is a cinch with Travelocity. With access to 400 air carriers and 1,000,000 properties worldwide, the choice is yours when picking your flights and hotels.
Why should I purchase my Woodstock vacation package via Travelocity?
We offer 24/7 customer support, top-quality service and a Price Match Guarantee. Life’s a great big journey — and we have enticing destinations for you to journey to all around the world. Wander with us and your wallet will thank you for it.
Can I save on my Woodstock car rental if I combine it with a hotel or flight?
You sure can — bundle your flight, hotel and car into a Woodstock vacation package and you’ll save a ton. With so much to see and do in the Woodstock area, that rental car will make it easy to explore. Once you’ve slid into the driver’s seat, get out on the wide open road and head toward Wrigley Field, a top attraction about 50 mi from Woodstock.
What is the best time of year to go to Woodstock?
If funds are a bit tight, is an ideal month to explore Woodstock, whereas is the priciest time of year. June, July and August is regarded as the peak season. If you’d prefer to avoid the masses, January, February and October tend to be quieter.
Which airport is best for Woodstock?
O’Hare Intl. Airport (ORD) (35 mi away from downtown), General Mitchell Intl. Airport (MKE) (50 mi away from central Woodstock) and Midway Intl. Airport (MDW) (50 mi away from central Woodstock) are the top options for Woodstock.
What is there to do in Woodstock?
Woodstock is overflowing with sights to discover, like McHenry County Fairgrounds and McHenry County Courthouse. These two fantastic attractions are on most visitors’ travel schedules.
Where should I stay when visiting Woodstock?
Many visitors opt to hit the hay at the Best Western Woodstock Inn. It’s sure to be a good base for your Woodstock escape.