Woodstock Vacation Packages 2025/2026 from $554

Woodstock flight + hotel vacation packages

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

The Shire Woodstock

$554

per person

Dec 23 - Dec 25

found 23 hours ago

Roundtrip non-stop flight included

Tampa (TPA) 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.

Winterplace at Okemo

Clock Tower Base Area

$1,025

per person

Dec 23 - Dec 25

found 23 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to Springfield (VSF)

Ski-in/ski-out access and an indoor pool are featured at this smoke-free aparthotel. Enjoy the hot tub and perks like free self parking and free WiFi. Express check-out, laundry facilities, and barbecue grills are also on offer.

Solitude Village at Okemo

Clock Tower Base Area

$989

per person

Dec 23 - Dec 25

found 23 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to Springfield (VSF)

Ski-in/ski-out access and an outdoor pool are featured at this smoke-free aparthotel. Enjoy the indoor pool and perks like free self parking and free WiFi. A gym, a hot tub, and a sauna are also on offer.

Okemo Mountain Lodging

Clock Tower Base Area

$929

per person

Dec 23 - Dec 25

found 23 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to Springfield (VSF)

This vacation home features laundry facilities. Take advantage of the free self parking.

Mountain Lodge at Okemo

Clock Tower Base Area

$910

per person

Dec 23 - Dec 25

found 23 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to Springfield (VSF)

Ski-in/ski-out access and a restaurant are featured at this smoke-free hotel. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy downhill skiing. Families will appreciate the onsite laundry facilities and babysitting.

Top Woodstock hotels deals

Woodstock Inn & Resort

Fourteen The Green, Woodstock, VT

$389 nightly

$428 total

Nov 16 - Nov 17

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

The Shire Woodstock

46 Pleasant St., Woodstock, VT

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$152 total

Nov 13 - Nov 14

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

$149 nightly

$164 total

Nov 5 - Nov 6

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.

Parking included

Free WiFi

On The River Inn

1653 West Woodstock Road, Woodstock, VT

$226 nightly

$249 total

Oct 26 - Oct 27

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.

Pool

Hot Tub

Sleep Woodstock Motel

4324 West Woodstock Road, Woodstock, VT

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$143 total

Oct 22 - Oct 23

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.

Pet friendly

Parking included

Lincoln Inn & Gallery

2709 West Woodstock Rd, Woodstock, VT

$324 nightly

$356 total

Oct 22 - Oct 23

Total with taxes and fees

This inn features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning. A fireplace in the lobby and a picnic area are also provided.

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

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.

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

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.

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.