Woodstock Vacation Packages 2026 from $554

Woodstock flight + hotel vacation packages

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

Mountain Lodge at Okemo

Clock Tower Base Area

$554

per person

May 21 - May 24

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Springfield (VSF)

A restaurant and a gym are featured at this hotel. Take advantage of ski passes and ski storage on site, and enjoy downhill skiing and sledding. Families will appreciate the onsite laundry facilities and babysitting.

Jackson Gore Village

Jackson Gore Base Area

$588

per person

May 21 - May 24

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Springfield (VSF)

Ski-in/ski-out access, 2 restaurants, and 3 hot tubs are all featured at this smoke-free hotel. 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.

Mount Snow Grand Summit Resort

$568

per person

May 21 - May 24

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Springfield (VSF)

Ski-in/ski-out access, a full-service spa, and 2 hot tubs are all featured at this smoke-free resort. Enjoy a meal from the restaurant and freebies like WiFi in public areas and an area shuttle. You'll appreciate the outdoor pool, bar/lounge, and laundry facilities.

Top Woodstock hotels deals

Woodstock Inn & Resort

Fourteen The Green Woodstock VT

$349 nightly

$384 total

Mar 22 - Mar 23

Total with taxes and fees

This luxury resort features a golf course, a full-service spa, and 4 restaurants. Enjoy the 2 indoor tennis courts and perks like free valet parking and free WiFi. Relax with a drink at one of the 2 bars/lounges and enjoy the 2 hot tubs and indoor pool.

Pool

Hot Tub

On The River Inn

1653 West Woodstock Road Woodstock VT

$193 nightly

$212 total

Mar 1 - Mar 2

Total with taxes and fees

This hotel features an indoor pool, a hot tub, and a restaurant. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

The Shire Woodstock

46 Pleasant St. Woodstock VT

Free Cancellation

Reserve now, pay when you stay

$156 nightly

$171 total

Mar 11 - Mar 12

Total with taxes and fees

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

Pet friendly

Parking included

The Jackson

43 Senior Lane Woodstock VT

$169 nightly

$186 total

Mar 1 - Mar 2

Total with taxes and fees

A restaurant and a bar/lounge are featured at this bed & breakfast. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, and a lobby fireplace are also on offer.

Lincoln Inn & Gallery

2709 West Woodstock Rd Woodstock VT

$204 nightly

$225 total

Mar 12 - Mar 13

Total with taxes and fees

This inn doesn't skimp on freebies - guests receive free WiFi and free self parking. A fireplace in the lobby and a picnic area are also provided.

Parking included

Free WiFi

Sleep Woodstock Motel

4324 West Woodstock Road Woodstock VT

Free Cancellation

Reserve now, pay when you stay

$138 nightly

$152 total

Mar 2 - Mar 3

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area, express check-in, and express check-out are also on offer.

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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

4.5/5(13 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.

Saskadena Six Ski Area

4.5/5(14 reviews)

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

Wild Swans gather on ice in a northern wetland

Lakota Lake

Commune with nature and explore the great outdoors at Lakota Lake during your travels in Woodstock. While in this quaint area, you can savor the top-notch restaurants.

Frequently asked questions

How much are vacation packages to Woodstock?

Packages, including flights and hotels in Woodstock, start from as little as $554. 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.