Deals on vacations and trips to Woodstock

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Woodstock flight + hotel vacation packages

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Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Clock Tower Base Area
per person
Jun 14 - Jun 16
found 1 day ago
Roundtrip flight included
Cedar Rapids (CID) 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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
per person
Jun 14 - Jun 16
found 1 day ago
Roundtrip flight included
Cedar Rapids (CID) 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.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
per person
Jun 22 - Jun 26
found 5 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) 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.
Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
per person
Jun 14 - Jun 16
found 1 day ago
Roundtrip flight included
Cedar Rapids (CID) 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.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
per person
Jun 14 - Jun 16
found 1 day ago
Roundtrip flight included
Cedar Rapids (CID) 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.

Top Woodstock hotels deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is $384 per night
$384
includes taxes & fees
$349 per night
Apr 23 - Apr 24
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

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Free Cancellation
Reserve now, pay when you stay
The price is $132 per night
$132
includes taxes & fees
$120 per night
Apr 23 - Apr 24
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
506 On the River Inn

506 On the River Inn

4 out of 5
1653 West Woodstock Road, Woodstock, VT
The price is $195 per night
$195
includes taxes & fees
$177 per night
Apr 23 - Apr 24
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
The Jackson

The Jackson

4 out of 5
43 Senior Lane, Woodstock, VT
The price is $273 per night
$273
includes taxes & fees
$248 per night
Apr 23 - Apr 24
This bed & breakfast doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.
Parking included
Free WiFi
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 $129 per night
$129
includes taxes & fees
$117 per night
Apr 23 - Apr 24
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
The Vesper

The Vesper

3 out of 5
21 Pleasant St, Woodstock, VT
The price is $111 per night
$111
includes taxes & fees
$100 per night
Apr 28 - Apr 29
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.
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

The house

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.

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

Woodstock Town Hall Theatre

4.5/5(5 reviews)

Get tickets for a show at Woodstock Town Hall Theatre, a theater with a story to tell in Woodstock. Wander the riverfront in this quaint area.

Woodstock Town Hall Theatre

Frequently asked questions

How much are vacation packages to Woodstock?
Packages, including flights and hotels in Woodstock, start from as little as $879. 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
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Woodstock showing a river or creek and a garden
Woodstock showing a bridge
Woodstock featuring heritage architecture