Woodstock Vacation Packages 2025/2026 from $617

Woodstock flight + hotel vacation packages

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

COHO Inn & Motor Lodge

Save 100% on your flight

$617

per person

Dec 27 - Jan 3

found 22 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Springfield (VSF)

A bar/lounge and a terrace are featured at this motel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A garden, a snack bar/deli, and a lobby fireplace are also on offer.

Stone Hearth Inn and Eatery

Save 100% on your flight

$849

per person

Dec 27 - Jan 3

found 22 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Springfield (VSF)

This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free buffet breakfast each morning. A garden is also provided.

The Shire Woodstock

$1,249

per person

Dec 24 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Springfield (VSF)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.

Jackson Gore Village

Jackson Gore Base Area

$1,929

per person

Dec 24 - Dec 28

found 1 day ago

Roundtrip non-stop flight included

Fort Lauderdale (FLL) to Springfield (VSF)

This smoke-free hotel features ski-in/ski-out access, a full-service spa, and 2 restaurants. There's a free ski shuttle, and ski lessons, ski passes and ski storage are available on site. Bring the family and enjoy the mini golf, playground, and arcade/game room.

Windham Hill Inn

$902

per person

Dec 27 - Jan 3

found 22 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Springfield (VSF)

A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. WiFi in public areas is free. A garden is also provided.

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.

Saskadena Six Ski Area

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

Frequently asked questions

How much are vacation packages to Woodstock?

Packages, including flights and hotels in Woodstock, start from as little as $617. 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 110 mi 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 11 mi east from inner Woodstock. You can also check out the deals to Rutland Southern Vermont Regional Airport (RUT), which is 20 mi 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.