Deals on vacations and trips to Woodstock

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Woodstock flight + hotel vacation packages

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Mountaineer Inn

Mountaineer Inn

2 out of 5
per person
Sep 18 - Sep 22
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Springfield (VSF)
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and express check-in are also on offer.
Chalet 239

Chalet 239

2 out of 5
per person
Sep 18 - Sep 22
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Springfield (VSF)
The motel doesn't skimp on freebies - guests receive free on-the-go breakfast and free self parking. A picnic area and a virtual front desk are also provided.
Windham Hill Inn

Windham Hill Inn

4 out of 5
Save 100% on your flight
per person
Sep 18 - Sep 22
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Springfield (VSF)
A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. WiFi in public areas is free. A garden is also provided.
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Save 100% on your flight
per person
Aug 30 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Springfield (VSF)
This smoke-free resort features ski-in/ski-out access, a full-service spa, and a restaurant. Enjoy the outdoor pool and perks like free valet parking and a free area shuttle. You'll appreciate the gym, bar/lounge, and laundry facilities.
Mount Snow Lodging

Mount Snow Lodging

3 out of 5
per person
Sep 18 - Sep 22
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Springfield (VSF)

Top Woodstock hotels deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
$499 nightly
The price is $549 total per night
$549 total
Aug 10 - Aug 11
Total includes 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
$223 nightly
The price is $245 total per night
$245 total
Jul 16 - Jul 17
Total includes 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
$164 nightly
The price is $180 total per night
$180 total
Jul 30 - Jul 31
Total includes 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
Sleep Woodstock Motel

Sleep Woodstock Motel

2 out of 5
4324 West Woodstock Road, Woodstock, VT
Free Cancellation
Reserve now, pay when you stay
$119 nightly
The price is $131 total per night
$131 total
Jul 21 - Jul 22
Total includes 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
The Jackson

The Jackson

4 out of 5
43 Senior Lane, Woodstock, VT
$198 nightly
The price is $218 total per night
$218 total
Jul 16 - Jul 17
Total includes 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
Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
2709 West Woodstock Rd, Woodstock, VT
$116 nightly
The price is $128 total per night
$128 total
Jul 20 - Jul 21
Total includes taxes and fees
This inn features free self parking and free WiFi in public areas. Enjoy the free self-serve 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

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

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 $362. 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