Deals on vacations and trips to Woodstock

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Woodstock flight + hotel vacation packages

Mountaineer Inn

Mountaineer Inn

2 out of 5
Price was $442, price is now $442 per person
per person
Mar 4 - Mar 7
Roundtrip flight included
Newark (EWR) to Springfield (VSF)
A seasonal outdoor pool is featured at this motel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace and a garden are also provided.

Top Woodstock hotels deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT, 05091
The price is $289 per night
$289
per night
Feb 26 - Feb 27
This smoke-free resort features a golf course, a full-service spa, and 4 restaurants. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at one of the 2 bars/lounges and enjoy the 2 indoor tennis courts and indoor pool.
506 On the River Inn

506 On the River Inn

4 out of 5
1653 West Woodstock Road, Woodstock, VT, 05091
The price is $269 per night
$269
per night
Jan 29 - Jan 30
This hotel features an indoor pool, a spa tub, and a restaurant. Enjoy the free ski shuttle and onsite ski storage. There's fun for all ages with a children's pool and a playground, and families will appreciate the picnic area.
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT, 05091
Free Cancellation
Reserve now, pay when you stay
The price is $177 per night
$177
per night
Jan 31 - Feb 1
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
Sleep Woodstock Motel

Sleep Woodstock Motel

2 out of 5
4324 West Woodstock Road, Woodstock, VT, 05091
The price is $175 per night
$175
per night
Jan 29 - Jan 30
Free WiFi in public areas is available at this motel. Take advantage of the free self parking.
The Lincoln Inn & Restaurant At The Covered Bridge

The Lincoln Inn & Restaurant At The Covered Bridge

3.5 out of 5
2709 W. Woodstock Road, Woodstock, VT, 05091
Get rates
This inn features a restaurant, a lazy river, and a bar/lounge. Enjoy the a rooftop terrace and perks like free self parking and free WiFi. A terrace, a garden, and a lobby fireplace are also on offer.
The Jackson House Inn

The Jackson House Inn

4 out of 5
43 Senior Lane, Woodstock, VT, 05091
Get rates
A bar/lounge and a terrace are featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like full breakfast and WiFi in public areas. A garden, a lobby fireplace, and a library are also on offer.
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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

Image for Suicide Six Ski Area

Suicide Six Ski Area

4.5/5(14 reviews)

Hit the slopes in Woodstock with a visit to Suicide Six Ski Area. Wander the riverfront in this quaint area.

Suicide Six Ski Area
Image for Billings Farm and Museum

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
Image for Woodstock Country Club

Woodstock Country Club

4.5/5(7 reviews)

Enjoy a round of golf in Woodstock at Woodstock Country Club. Wander the riverfront in this quaint area.

Woodstock Country Club

Frequently asked questions

How much are vacation packages to Woodstock?
Adventure awaits in Woodstock, with Travelocity vacation packages from as little as $442. In addition to flights and hotels, these terrific deals make it a breeze to explore all corners of the world.
How long should my Woodstock vacation be?
Generally, 2 nights is what many tourists book for their Woodstock trip. That’s a good starting point, but there’s loads more to discover if you give yourself a little longer.
Where can I get the best vacation package deals for Woodstock?
Snapping up the best package deal to Woodstock is a cinch with Travelocity. With access to 400 air carriers and 1,000,000 properties across the globe, you’re spoiled for choice when selecting your flights and hotels.
Why should I book my Woodstock vacation package via Travelocity?
From enticing destinations to one-of-a-kind experiences, we have everything you need to satisfy your travel desires. Our friendly 24/7 customer support will also ensure you’re taken care of while you’re on your getaway. And don’t worry if you spot a cheaper price on your booking, we’ll match it. That’s our Price Match Guarantee.
Can I save money on my Woodstock car rental if I bundle it with a hotel or flight?
Sure can — combine your flight, car and hotel into a Woodstock vacation package and you can save plenty. With so much to discover in the Woodstock area, that set of wheels will make exploring a joy. Once you’ve settled into the driver’s seat, hit the wide open road and find your way to Fenway Park, a well-known sight approximately 110 mi from Woodstock.
What is the best time of year to go to Woodstock?
If you really want to wander wisely, is one of the best times to do it. That’s when you’ll find hotel rates tumble. By way of comparison, prices are at their highest around . are the most popular times to stay in Woodstock, so brace for snaking lines at major attractions. Prefer to travel outside peak season? You’ll find thinner crowds in .
Which airport is best for Woodstock?
Lebanon Municipal Airport (LEB) is where many travelers land. You’ll find it 10 mi east from inner Woodstock. You can also check out the fares to Rutland Southern Vermont Regional Airport (RUT), which is 20 mi away from central Woodstock.
What is there to do in Woodstock?
There is a certain kind of magic as you wander through the streets of Woodstock. Suicide Six Ski Area and Woodstock Country Club are just a couple of highlights that make this city such a sought-after destination, so add them to your to-do list.
Where should I stay when visiting Woodstock?
The The Shire Woodstock is popular with many travelers. Book as soon as possible before it’s too late.
Can I go on vacation to Woodstock at this time?
Discover all the info you need to know about travel restrictions and quarantine policies before you fly to Woodstock. Our Covid-19 Travel Advisor is full of advice to help make your vacation as hassle-free as possible.