Woodstock Vacations 2025 from CA $1,285

Woodstock flight + hotel packages

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

Hampton Inn Brattleboro

per person

Aug 1 - Aug 8

found 22 hours ago

Roundtrip non-stop flight included

Calgary (YYC) 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.

The Shire Woodstock

per person

Aug 29 - Sep 1

found 1 day ago

Roundtrip flight included

Winnipeg (YWG) to Springfield (VSF)

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.

Winterplace at Okemo

Clock Tower Base Area

per person

Aug 1 - Aug 8

found 22 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Springfield (VSF)

Stay at this 4-star ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.

Jackson Gore Village

Jackson Gore Base Area

per person

Aug 1 - Aug 8

found 22 hours ago

Roundtrip non-stop flight included

Calgary (YYC) 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.

Solitude Village at Okemo

Clock Tower Base Area

per person

Aug 1 - Aug 8

found 22 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Springfield (VSF)

Stay at this 4-star ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.

Top Woodstock hotels deals

Woodstock Inn & Resort

Fourteen The Green, Woodstock, VT

Get rates

Stay at this 4.5-star 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 Shire Woodstock

46 Pleasant St., Woodstock, VT

Free cancellation

Reserve now, pay when you stay

Get rates

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.

On The River Inn

1653 West Woodstock Road, Woodstock, VT

Get rates

Stay at this 4-star 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 Jackson

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

Sleep Woodstock Motel

4324 West Woodstock Road, Woodstock, VT

Free cancellation

Reserve now, pay when you stay

Get rates

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

2709 West Woodstock Rd, Woodstock, VT

Get rates

Stay at this 3-star inn in Woodstock. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Union Arena Community Center and Ottaquechee River are located nearby.

Breakfast included

Parking included

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

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.

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.

Woodstock Town Hall Theatre

Get tickets for a show at Woodstock Town Hall Theatre, a theater with a story to tell in Woodstock. Wander the riverfront in this quaint 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 $1,285. 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.