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Woodstock flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Colonial Motel

Colonial Motel

3 out of 5
Price was CA $1,107, price is now CA $1,064 per person
CA $1,064
per person
Nov 30 - Dec 4
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
Book a stay at this business-friendly motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brattleboro Bowl and New England Center for Circus Arts are located nearby.
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was CA $1,668, price is now CA $1,416 per person
CA $1,416
per person
Nov 30 - Dec 4
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Sweet Pond State Park and Shattuck Brook Wildlife Management Area are located nearby.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was CA $1,393, price is now CA $1,238 per person
CA $1,238
per person
Nov 30 - Dec 4
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was CA $1,376, price is now CA $1,252 per person
CA $1,252
per person
Nov 30 - Dec 3
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
Stay at this B&B in Jericho. Enjoy free breakfast, free WiFi, and in-room massages. Our guests praise the breakfast in our reviews. Popular attractions Veterans' Park and Mills Riverside Park are located nearby.
1846 Inn and Tavern

1846 Inn and Tavern

3 out of 5
Price was CA $1,387, price is now CA $1,322 per person
CA $1,322
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
Stay at this inn in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.

Top Woodstock hotels deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is CA $946 per night
CA $946
CA $1,103 total
Oct 27 - Oct 28
includes taxes & fees
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Middle Covered Bridge and Woodstock Town Hall Theatre are located nearby.
Pool
Hot tub
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
The price is CA $334 per night
CA $334
CA $367 total
Oct 26 - Oct 27
includes taxes & fees
Stay at this B&B in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast in our reviews. Popular attractions Union Arena Community Center and Five Elm Arches are located nearby.
Parking included
Free WiFi
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
The price is CA $352 per night
CA $352
CA $418 total
Oct 27 - Oct 28
includes taxes & fees
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
Pet-friendly
Parking included
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
The price is CA $335 per night
CA $335
CA $400 total
Oct 27 - Oct 28
includes taxes & fees
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Union Arena Community Center and Five Elm Arches are located nearby.
Pool
Hot tub
Sleep Woodstock Motel

Sleep Woodstock Motel

2 out of 5
4324 West Woodstock Road Woodstock VT
The price is CA $137 per night
CA $137
CA $206 total
Oct 27 - Oct 28
includes taxes & fees
Stay at this motel in Woodstock. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ottaquechee River and Union Arena Community Center are located nearby.
Pet-friendly
Parking included
Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
2709 Woodstock Rd Woodstock VT
The price is CA $929 per night
CA $929
CA $1,022 total
Oct 1 - Oct 2
includes taxes & fees
Stay at this guesthouse in Woodstock. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions Union Arena Community Center and Ottaquechee River are located nearby.
Parking included
Free WiFi
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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.

Stay near popular Woodstock attractions

A herd of cows grazing in a fenced pasture with trees and a building in the background.

Billings Farm and Museum

9.2/10 (84 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.
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Woodstock Vacations

You don't have to know everything about the place to discover the true essence of Woodstock, but you should know a few basic things before you go.

To help get you oriented, Woodstock lies 110 miles (177 kilometers) to the northwest of the well-known city of Boston.

Ready to meet some of the locals? 900 people call this part of Central Vermont- Killington home.

Places to visit in Woodstock

There's nothing like staring at a blanket of snow and knowing you've got the whole day ahead to carve up the slopes. Dig out your goggles and strap into your skis — Suicide Six Ski Area awaits! Seeking some more options? If you have an inquisitive mind, go to Billings Farm and Museum. You never know what you'll discover here! And that's not all there is. Nothing gives us an insight into yesteryear quite like old houses. Why not take a tour around Marsh-Billings-Rockefeller National Historical Park and find out what went on within its walls?

Where do you fly into for Woodstock?

Plug in your headphones and select an in-flight movie. Before long, you'll touch down at Lebanon Municipal Airport (LEB). It's 10 miles (16 kilometers) from the center of Woodstock.

Frequently asked questions

How much are vacation packages to Woodstock?
Packages, including flights and hotels in Woodstock, start from as little as CA $1,064. Make your daydreams come true and secure your dream vacation with Travelocity today.
How long should my Woodstock vacation be?
Most visitors stay in Woodstock for about 2 nights. That being said, traveling is all about finding new adventures and losing yourself in the moment — why not stay a few additional nights so you can do just that?
Where can I get the best vacation package deals for Woodstock?
You'll find awesome Woodstock package deals with Travelocity. Mix and match from as many as 400 partner airlines and 1,000,000 properties worldwide and turn those vacation daydreams into reality.
Why should I book my Woodstock vacation package with Travelocity?
We've got 24/7 customer support, top-quality service and a Price Match Guarantee. Life is one big journey — and we have exciting destinations for you to journey to all across the world. Roam with us and your bank balance will thank you for it.
Can I save on my Woodstock car rental if I combine it with hotels and flights?
With a Woodstock vacation package, you can combine your car, hotel and flight bookings and save some serious money. If you want to see the best of this fabulous area, why not make a beeline for Fenway Park? This must-see attraction is 177 kilometers from Woodstock. With your own wheels, you'll be there in no time.
Which airport is best for Woodstock?
Lebanon Municipal Airport (LEB) is where many visitors disembark. It's situated around 18 kilometers east from inner Woodstock. You can also check out the deals to Rutland Southern Vermont Regional Airport (RUT), which is 32 kilometers away from central Woodstock.
What is there to do in Woodstock?
While hopping off the tourist trail can be rewarding, you shouldn't miss the big sights that make a destination famous. Billings Farm and Museum and Woodstock Town Hall Theatre are a couple of them in Woodstock.
Where should I stay when visiting Woodstock?
The The Shire Woodstock is the top choice of many travelers. Book now to avoid missing out.

Photos of local treasures

Browse Woodstock vacation photos for more inspiration

A red convertible car parked in front of a brick house with black shutters and a white picket fence.
A street with various shops, including 'The Prince & The Pauper' and 'Philox'.
A river with rocks, surrounded by trees with orange leaves, a grassy area, and a building in the background.
A wooden covered bridge with signs reading "Woodstock Middle Bridge 1969" and "Slippery When Wet."
A historic brick building with a sign reading "Woodstock Pharmacy" and various storefronts below.

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