Deals on vacations and trips to Woodstock

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Woodstock flight + hotel vacation packages

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Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $852, price is now $764 per person
$764
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop 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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,782, price is now $1,451 per person
$1,451
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $978, price is now $888 per person
$888
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was $1,149, price is now $1,051 per person
$1,051
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Ski-in/ski-out access and an indoor pool are featured at this smoke-free aparthotel. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the hot tub and conveniences like express check-out and laundry facilities.
Solitude Village at Okemo by Vail Resorts

Solitude Village at Okemo by Vail Resorts

4 out of 5
Clock Tower Base Area
Price was $1,050, price is now $967 per person
$967
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
This smoke-free aparthotel's ski-in/ski-out access and 2 hot tubs are some of the highlights. Enjoy the gym and perks like free self parking and free WiFi. A sauna is also provided.

Top Woodstock hotels deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$479 nightly
The price is $527 total per night
$527 total
Aug 16 - Aug 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
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$239 nightly
The price is $263 total per night
$263 total
Jul 26 - Jul 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
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Free Cancellation
Reserve now, pay when you stay
$276 nightly
The price is $303 total per night
$303 total
Jul 21 - Jul 22
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.
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
$179 nightly
The price is $197 total per night
$197 total
Jul 21 - Jul 22
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
Sleep Woodstock Motel

Sleep Woodstock Motel

2 out of 5
4324 West Woodstock Road Woodstock VT
Free Cancellation
Reserve now, pay when you stay
$86 nightly
The price is $95 total per night
$95 total
Jul 22 - Jul 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

Lincoln Inn & Gallery

3 out of 5
2709 Woodstock Rd Woodstock VT
Free Cancellation
Reserve now, pay when you stay
$187 nightly
The price is $206 total per night
$206 total
Jul 20 - Jul 21
Total with taxes and fees
This guesthouse 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.
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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.

Stay near popular Woodstock attractions

A herd of cows grazing in a fenced pasture with trees and a building in the background.

Billings Farm and Museum

9.2/10 (84 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.
See properties

Frequently asked questions

How much are vacation packages to Woodstock?
Packages, including flights and hotels in Woodstock, start from as little as $764. 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

Browse Woodstock vacation photos for more inspiration

A red convertible car parked in front of a brick house with black shutters and a white picket fence.
A street with various shops, including 'The Prince & The Pauper' and 'Philox'.
A river with rocks, surrounded by trees with orange leaves, a grassy area, and a building in the background.
A wooden covered bridge with signs reading "Woodstock Middle Bridge 1969" and "Slippery When Wet."
A historic brick building with a sign reading "Woodstock Pharmacy" and various storefronts below.

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