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Woodstock Vacations

Pack those stellar shades. We have Woodstock vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Woodstock – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Woodstock vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Woodstock

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Woodstock vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Woodstock well.

Top Hotel Deals

See all 121 Hotels in Woodstock
Best Western Woodstock Inn

Best Western Woodstock Inn

990 Lake Avenue, Woodstock
3.0 out of 5.0

Conveniently located near the ski slopes, this Woodstock hotel is within 1 mi (2 km) of McHenry County Fairgrounds, Woodstock Square, and Woodstock City Hall. ...

$68

$68
Super 8 Woodstock

Super 8 Woodstock

1220 Davis Rd, Woodstock
2.0 out of 5.0

Situated in Woodstock, this motel is within 3 mi (5 km) of McHenry County Fairgrounds, Woodstock Square, and Woodstock City Hall. Woodstock Opera House and Old ...

$53

$53
Quality Inn

Quality Inn

1785 South Eastwood Drive, Woodstock
3.0 out of 5.0

Located in the heart of Woodstock, this hotel is within 2 mi (3 km) of McHenry County Fairgrounds, Woodstock Square, and Woodstock City Hall. Woodstock Opera ...

$51

$51
Grand Geneva Resort & Spa

Grand Geneva Resort & Spa

7036 Grand Geneva Wy, Lake Geneva
4.5 out of 5.0

Located near the slopes, this Lake Geneva resort is within a 5-minute walk of The Brute Golf Course and The Highlands Golf Course and close to winter sports ...

$139

$139
Lake Lawn Resort

Lake Lawn Resort

2400 E Geneva St, Delavan
4.0 out of 5.0

Lake Lawn Resort is 7 minutes by car from the charming antique shops of downtown Delavan. Guests can join a boat tour of Lake Delavan right outside the resort, ...

$84

$84
The Cove Of Lake Geneva

The Cove Of Lake Geneva

111 Center St, Lake Geneva
4.0 out of 5.0

This family-friendly Lake Geneva hotel is located in the business district, within a 5-minute walk of Riviera Ballroom and Lake Geneva Cruise Line. Riviera Beach ...

$88

$88
Geneva Inn

Geneva Inn

N2009 S Lake Shore Drive, Lake Geneva
3.5 out of 5.0

Situated on a lake, this hotel is 0.2 mi (0.3 km) from Big Foot Beach State Park and within 3 mi (5 km) of Paradise Golf Park and Riviera Ballroom. Lake Geneva ...

$105

$105
Abbey Resort and Avani Spa

Abbey Resort and Avani Spa

269 Fontana Boulevard, Fontana
4.0 out of 5.0

Offering direct access to the beach, this Fontana resort is 2.8 mi (4.5 km) from Yerkes Observatory and within 6 mi (10 km) of Geneva Lake and Black Point Estate. ...

$119

$119
Hyatt Place Chicago/Hoffman Estates

Hyatt Place Chicago/Hoffman Estates

2750 Greenspoint Pkwy, Hoffman Estates
3.5 out of 5.0

Hyatt Place Chicago/Hoffman Estates is an 8-minute drive from the massive Sears Centre Arena, and 10 minutes from Woodfield Mall, the largest shopping facility ...

$80

$80
Chicago Marriott Northwest

Chicago Marriott Northwest

4800 Hoffman Blvd, Hoffman Estates
3.5 out of 5.0

Located in the Prairie Stone Business Park, this eight-story hotel is a half-mile from Northern Illinois University Conference Center, seven miles from Woodfield ...

$89

$89