Woodstock Vacation Packages 2025 from $606

Woodstock flight + hotel vacation packages

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

Sinclair Inn Bed and Breakfast

per person

Mar 26 - Mar 31

found 20 hours ago

Roundtrip flight included

Orlando (MCO) to Springfield (VSF)

This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast and free WiFi. A garden and a picnic area are also provided.

Top Woodstock hotels deals

Woodstock Inn & Resort

Fourteen The Green, Woodstock, VT

$417

includes taxes & fees

$379 per night

Feb 9 - Feb 10

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 spa tubs and indoor pool.

The Shire Woodstock

46 Pleasant St., Woodstock, VT

$156

includes taxes & fees

$140 per night

Feb 5 - Feb 6

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

Sleep Woodstock Motel

4324 West Woodstock Road, Woodstock, VT

$140

includes taxes & fees

$128 per night

Jan 27 - Jan 28

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.

506 On the River Inn

1653 West Woodstock Road, Woodstock, VT

$214

includes taxes & fees

$195 per night

Jan 26 - Jan 27

This hotel features an indoor pool, a spa tub, and a restaurant. There's a free ski shuttle, and ski passes and ski storage are available on site. There's fun for all ages with a children's pool and a playground, and families will appreciate the picnic area.

The Jackson

43 Senior Lane, Woodstock, VT

$232

includes taxes & fees

$211 per night

Jan 26 - Jan 27

This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free continental breakfast each morning. A terrace, a garden, and a lobby fireplace are also on offer.

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

Get rates

A garden is available at this cottage.

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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 $606. 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.