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Woodstock flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was CA $1,596, price is now CA $1,570 per person
CA $1,570
per person
Dec 26 - Dec 28
found 5 hours ago
Roundtrip flight included
Halifax (YHZ) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was CA $1,750, price is now CA $1,695 per person
CA $1,695
per person
Dec 26 - Dec 28
found 5 hours ago
Roundtrip flight included
Halifax (YHZ) 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.
The Hermitage Inn Vermont

The Hermitage Inn Vermont

4 out of 5
Price was CA $2,145, price is now CA $2,087 per person
CA $2,087
per person
Dec 26 - Dec 28
found 5 hours ago
Roundtrip flight included
Halifax (YHZ) to Springfield (VSF)
Book a stay at this golf inn in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Back Draft are located nearby.
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
Price was CA $1,697, price is now CA $1,680 per person
CA $1,680
per person
Dec 26 - Dec 28
found 5 hours ago
Roundtrip flight included
Halifax (YHZ) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Black Mountain Inn

Black Mountain Inn

2 out of 5
Price was CA $1,660, price is now CA $1,649 per person
CA $1,649
per person
Dec 26 - Dec 28
found 5 hours ago
Roundtrip flight included
Halifax (YHZ) to Springfield (VSF)
Stay at this hotel 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 United States Navy Seabee Bridge 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 $467 per night
CA $467
CA $576 total
Nov 30 - Dec 1
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 Quechee Gorge Bridge and Middle Covered Bridge are located nearby.
Pool
Hot tub
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
The price is CA $185 per night
CA $185
CA $232 total
Dec 2 - Dec 3
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
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 CA $167 per night
CA $167
CA $199 total
Nov 22 - Nov 23
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 Quechee Gorge Bridge and Billings Park and Trail are located nearby.
Pet-friendly
Parking included
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
The price is CA $175 per night
CA $175
CA $192 total
Nov 15 - Nov 16
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
Sleep Woodstock Motel

Sleep Woodstock Motel

2 out of 5
4324 West Woodstock Road Woodstock VT
Free cancellation
Reserve now, pay when you stay
The price is CA $116 per night
CA $116
CA $182 total
Nov 19 - Nov 20
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
Free cancellation
Reserve now, pay when you stay
The price is CA $268 per night
CA $268
CA $295 total
Nov 17 - Nov 18
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.
See properties

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 $1,570. 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 wooden covered bridge with a sign reading 'Slippery When Wet' and a sign above the entrance that says 'Michael's Bridge.'
A wooden covered bridge with signs reading "Woodstock Middle Bridge 1969" and "Slippery When Wet."
A covered wooden bridge with a sign reading "Woodstock Middle Bridge 1893."
A wooden covered bridge with a sign reading "Woodford Middle Bridge."
A wooden covered bridge with a sign reading "Woodstock Middle Bridge 1969" and another warning "Slippery When Wet".

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