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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 71 Hotels in Woodstock
Best Western Plus Woodstock Inn & Suites

Best Western Plus Woodstock Inn & Suites

811 Athlone Avenue, Woodstock
3.0 out of 5.0

Located in the heart of Woodstock, this eco-friendly hotel is within 2 mi (3 km) of Southside Park, Church Of The Epiphany, and Woodstock Art Gallery. Woodstock ...

$81

$81
Château la Motte Guest House

Château la Motte Guest House

210 Vansittart Avenue, Woodstock
4.0 out of 5.0

Situated in the historical district, this bed & breakfast is within a 15-minute walk of Woodstock Art Gallery and Woodstock Museum National Historic Site. Woodstock ...

Days Inn Woodstock

Days Inn Woodstock

560 Norwich Avenue, Woodstock
2.0 out of 5.0

Situated in Woodstock, this hotel is 1.1 mi (1.7 km) from Southside Park and within 3 mi (5 km) of Church Of The Epiphany and Woodstock Raceway. Woodstock Art ...

$57

$57
Quality Hotel and Suites Woodstock

Quality Hotel and Suites Woodstock

580 Bruin Blvd, Woodstock
3.0 out of 5.0

Situated in Woodstock, this eco-friendly hotel is 1 mi (1.7 km) from Southside Park and within 3 mi (5 km) of Woodstock Art Gallery and Church Of The Epiphany. ...

$82

$82
Holiday Inn Express & Suites Woodstock South

Holiday Inn Express & Suites Woodstock South

510 Norwich Avenue, Woodstock
3.0 out of 5.0

Located in the heart of Woodstock, this hotel is within 2 mi (3 km) of Southside Park, Church Of The Epiphany, and Woodstock Raceway. Woodstock Art Gallery is ...

$93

$93
Econo Lodge Woodstock

Econo Lodge Woodstock

15 Graham St, Woodstock
2.5 out of 5.0

Situated in Woodstock, this hotel is within a 5-minute walk of Woodstock Art Gallery and Church Of The Epiphany. Southside Park and Woodstock Raceway are also ...

$59

$59
Westmount Motel

Westmount Motel

585076 Beachville Rd, Woodstock
2.5 out of 5.0

Situated in Woodstock, this motel is within 2 mi (3 km) of Woodstock Art Gallery, Church Of The Epiphany, and Southside Park. Woodstock Raceway is 2.4 mi (3.8 ...

Tulip Motel

Tulip Motel

1275 Dundas St, Woodstock
2.5 out of 5.0

Situated in Woodstock, this motel is within 3 mi (5 km) of Woodstock Raceway, Church Of The Epiphany, and Woodstock Art Gallery. Southside Park is 2.6 mi (4.2 ...

Rose Court Bed & Breakfast

Rose Court Bed & Breakfast

251 Ferguson Drive, Woodstock
3.5 out of 5.0

Situated in Woodstock, this bed & breakfast is within 2 mi (3 km) of Southside Park, Church Of The Epiphany, and Woodstock Art Gallery. Woodstock Raceway is ...

Mariner Motel

Mariner Motel

1252 Dundas Street East, Woodstock
3.0 out of 5.0

Situated in Woodstock, this motel is 1.2 mi (2 km) from Woodstock Raceway and within 3 mi (5 km) of Church Of The Epiphany and Woodstock Art Gallery. Southside ...

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.