Vermont may have travel restrictions in place, including self-quarantine, due to COVID-19.

Find out moreOpens in new tab or window

Book Exclusive Woodstock Vacation Packages

Choose two or more items and save on your trip:

Top Woodstock hotels deals

Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is $228 per night
This luxury resort features a golf course, a full-service spa, and 4 restaurants. Traveling on business? Take advantage of the business center and free WiFi ...
506 On the River Inn
506 On the River Inn
4 out of 5
1653 West Woodstock Road, Woodstock, VT
The price is $169 per night
This hotel features an indoor pool, a spa tub, and a restaurant. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the ...
The Shire Woodstock
The Shire Woodstock
3 out of 5
46 Pleasant St., Woodstock, VT
Free Cancellation
Reserve now, pay when you stay
The price is $109 per night
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
Sleep Woodstock Motel
Sleep Woodstock Motel
2 out of 5
4324 West Woodstock Road, Woodstock, VT
The price is $158 per night
Free WiFi in public areas is available at this motel.
The Blue Horse Inn
The Blue Horse Inn
3.5 out of 5
3 Church Street, Woodstock, VT
The price is $211 per night
A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi ...
The Jackson House Inn
The Jackson House Inn
4 out of 5
43 Senior Lane, Woodstock, VT
The price is $224 per night
A bar/lounge and a terrace are featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like full breakfast and WiFi ...
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 in Woodstock

Image for Billings Farm and Museum

Billings Farm and Museum

4.5/5(13 reviews)

You can study the exhibits at Billings Farm and Museum, a museum with a storied past, during your trip to Woodstock. Wander the riverfront in this quaint area.

Billings Farm and Museum
Image for Marsh-Billings-Rockefeller National Historical Park

Marsh-Billings-Rockefeller National Historical Park

Explore the lovely green spaces of Marsh-Billings-Rockefeller National Historical Park and enjoy the ski slopes in Woodstock. Stroll along the riverfront or discover the mountain views in this quaint area.

Marsh-Billings-Rockefeller National Historical Park
Image for Killington Resort

Killington Resort

4.5/5(420 reviews)

Terrain parks, hiking trails, golf, après-ski entertainment and a range of slopes for all levels of skiers welcome visitors to this resort in the Green Mountains.

Killington Resort

Frequently asked questions

How much are vacation packages to Woodstock?
Your travel dreams can come to life in Woodstock from as little as . Our affordable package deals include flights and hotels, so you’ll find booking is nice and easy. The only thing you’ll have to concentrate on is what amazing attraction you’ll head to first.
How long should my Woodstock vacation be?
Your Woodstock trip can be as long or as short as you want, but most travelers stay about 2 nights. Eager to head off the beaten path and discover some hidden treasures? Lock in a couple of extra nights and see another side of this place.
Where can I get the best vacation package deals for Woodstock?
It’s simple — look no further than Travelocity. With as many as 400 air carriers and 665,000 properties around the world, it’s a breeze to find a Woodstock package deal that suits your needs.
Why should I purchase my Woodstock vacation package via Travelocity?
From exciting destinations to thrilling experiences, we have everything you need to appease your wanderlust. Our 24/7 support will also make sure you’re being well taken care of during your vacation. And don’t panic if you spot a better price on your reservation, we’ll match it. That’s our Price Match Guarantee.
Will I save money on my Woodstock car rental if I combine it with my hotel or flight?
With a Woodstock vacation package, you can bundle your car, hotel and flight bookings and save loads. If you want to discover the best of this fabulous destination, why not start with Fenway Park? This must-see attraction is 112 mi from Woodstock. With your own wheels, you’ll be there in a jiffy.
What is the best time of year to go to Woodstock?
are the most popular months for travelers to visit, while tend to be less busy. If you’re traveling on a shoestring, think about visiting around . is regarded as the costliest time of year to stay here.
Which airport is best for Woodstock?
Lebanon, NH (LEB-Lebanon Municipal), 11 mi east of the city center, is where many visitors start their adventures in Woodstock. But it’s possible that Rutland, VT (RUT-Rutland Southern Vermont Regional) (22 mi away from central Woodstock) could be the more convenient option for you.
What is there to do in Woodstock?
Suicide Six Ski Area should be on your to-do list. Once you’ve crossed off this top attraction, amble through the streets of Woodstock and learn what really makes this exciting destination tick.
Where should I stay when visiting Woodstock?
For the ultimate luxury getaway in Woodstock, reserve a room at the 506 On the River Inn (4.0 stars) or The Jackson House Inn (4.0 stars). These in-demand hotels boast beautiful furnishings and fantastic amenities.

^Savings based on all package bookings with Flight + Hotel made on Travelocity.com from as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.