Book Exclusive Woodstock Vacation Packages

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Woodstock flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was CA $1,059, price is now CA $907 per person
CA $907
per person
May 21 - May 24
found 1 day 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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $1,158, price is now CA $1,021 per person
CA $1,021
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
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.
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was CA $963, price is now CA $908 per person
CA $908
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and 2 hot tubs. Popular attractions Mount Snow and Tumbleweed Ski Lift are located nearby.
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 out of 5
Price was CA $1,361, price is now CA $1,342 per person
CA $1,342
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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 Brattleboro Bowl and New England Center for Circus Arts are located nearby.
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
Price was CA $1,009, price is now CA $1,004 per person
CA $1,004
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. 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.

Top Woodstock hotels deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is CA $429 per night
CA $429
CA $533 total
Apr 5 - Apr 6
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
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
The price is CA $194 per night
CA $194
CA $264 total
Apr 20 - Apr 21
includes taxes & fees
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and a fitness center. 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 $161 per night
CA $161
CA $191 total
Apr 1 - Apr 2
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
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 $108 per night
CA $108
CA $167 total
Mar 31 - Apr 1
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
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
The price is CA $311 per night
CA $311
CA $342 total
Apr 1 - Apr 2
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
Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
2709 West Woodstock Rd Woodstock VT
The price is CA $200 per night
CA $200
CA $220 total
Apr 7 - Apr 8
includes taxes & fees
Stay at this inn 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.

Popular places to visit

Billings Farm and Museum, Woodstock Vermont USA

Billings Farm and Museum

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
Saskadena Six Ski Area

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
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

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 $907. 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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