Deals on vacations and trips to Woodstock

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Woodstock flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
per person
Jan 6 - Jan 8
found 16 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
per person
Jan 6 - Jan 8
found 16 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Springfield (VSF)
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

The Shire Woodstock

3 out of 5
per person
Jan 18 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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.
The Vesper

The Vesper

3 out of 5
per person
Jan 18 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Springfield (VSF)
This bed & breakfast doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A virtual front desk are provided for your convenience.

Top Woodstock hotels deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is $373 per night
$373
includes taxes & fees
$339 per night
Dec 16 - Dec 17
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.
Pool
Hot Tub
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Free Cancellation
Reserve now, pay when you stay
The price is $206 per night
$206
includes taxes & fees
$184 per night
Nov 24 - Nov 25
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

Sleep Woodstock Motel

2 out of 5
4324 West Woodstock Road, Woodstock, VT
Free Cancellation
Reserve now, pay when you stay
The price is $120 per night
$120
includes taxes & fees
$109 per night
Nov 24 - Nov 25
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
506 On the River Inn

506 On the River Inn

4 out of 5
1653 West Woodstock Road, Woodstock, VT
The price is $219 per night
$219
includes taxes & fees
$199 per night
Nov 24 - Nov 25
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.
Pool
Hot Tub
The Jackson House Inn

The Jackson House Inn

4 out of 5
43 Senior Lane, Woodstock, VT
The price is $218 per night
$218
includes taxes & fees
$198 per night
Nov 24 - Nov 25
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.
Breakfast included
Parking included
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

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

Get rates
A garden is available at this cottage.
Kitchen
Washer
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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

The house

Billings Farm and Museum

4.5/5(13 reviews)

Rich with history, Billings Farm and Museum is a cultural attraction worth visiting in Woodstock. Wander the riverfront in this quaint area.

Billings Farm and Museum
When visiting Woodstock, Vermont, one not-to-miss outdoor attraction is the Marsh - Billings - Rockefeller National Historical Park, the first National Park in Vermont. The site is full of ambient trails with different atmospheres, whether you want to summit a mountain, run through a field or picnic on a lovely lake. Here you see The Pogue, a 14-acre

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.

Marsh-Billings-Rockefeller National Historical Park

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.

Saskadena Six Ski Area

Frequently asked questions

How much are vacation packages to Woodstock?
Packages, including flights and hotels in Woodstock, start from as little as $522. 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.

Photos of local treasures

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Woodstock featuring a house
Woodstock which includes street scenes
Woodstock showing a river or creek and a garden
Woodstock showing a bridge
Woodstock featuring heritage architecture