Book Exclusive Woodstock Vacation Packages

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Woodstock flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
per person
Jun. 6 - Jun. 8
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
Stay at this 3-star spa resort in West Dover. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Mount Snow and Ego Alley Ski Lift are located nearby.
Inn At Mount Snow

Inn At Mount Snow

2 out of 5
per person
Jun. 6 - Jun. 8
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
Book a stay at this ski hotel in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Snow Lake are located nearby.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
per person
Jun. 6 - Jun. 8
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
Stay at this 3-star spa hotel in Ludlow. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Jackson Gore Parking are located nearby.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
per person
Jun. 6 - Jun. 8
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
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 Woodstock Town Hall Theatre and Red Wagon Toy Company 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 $428 per night
CA $428
CA $534 total
includes taxes & fees
23 Mar - 24 Mar
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 Woodstock Town Hall Theatre and Red Wagon Toy Company are located nearby.
Pool
Hot tub
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 $146 per night
CA $146
CA $160 total
includes taxes & fees
26 Mar - 27 Mar
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
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 $197 per night
CA $197
CA $230 total
includes taxes & fees
30 Mar - 31 Mar
Stay at this 3-star 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
506 On the River Inn

506 On the River Inn

4 out of 5
1653 West Woodstock Road, Woodstock, VT
The price is CA $256 per night
CA $256
CA $282 total
includes taxes & fees
23 Mar - 24 Mar
Stay at this 4-star ski hotel in Woodstock. Enjoy free WiFi, free parking, and a free ski shuttle. 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 Jackson

The Jackson

4 out of 5
43 Senior Lane, Woodstock, VT
Get rates
Stay at this 4-star B&B in Woodstock. Enjoy free WiFi, free parking, and a garden. 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 Vesper

The Vesper

3 out of 5
21 Pleasant St, Woodstock, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $181 per night
CA $181
CA $200 total
includes taxes & fees
27 Mar - 28 Mar
Stay at this 3-star B&B in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Billings Park and Trail and Dana House Museum are located nearby.
Breakfast included
Parking included
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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.

Popular places to visit

Billings Farm and Museum

Billings Farm and Museum

5/5(1 review)

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
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

Saskadena Six Ski Area

Hit the slopes in Woodstock with a visit to Saskadena Six Ski Area. Wander the riverfront in this quaint area.

Saskadena Six Ski Area

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 $847. 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

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Woodstock featuring a house
Woodstock showing street scenes
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Woodstock showing a bridge
Woodstock featuring heritage architecture