Deals on vacations and trips to Woodstock

Save when you book Woodstock, VT package deals

Choose two or more items and save on your trip:

Top Woodstock hotels deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is $289 per night
$289
per night
Apr 21 - Apr 22
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.
Hot Tub
Pet friendly
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 $153 per night
$153
per night
Apr 24 - Apr 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 $124 per night
$124
per night
Apr 22 - Apr 23
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 $239 per night
$239
per night
Apr 21 - Apr 22
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.
Hot Tub
Pool
The Jackson House Inn

The Jackson House Inn

4 out of 5
43 Senior Lane, Woodstock, VT
The price is $263 per night
$263
per night
Apr 19 - Apr 20
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.
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
Stay at this cottage in Woodstock. Enjoy onsite parking, a patio, and a TV. Popular attractions Taftsville Covered Bridge and Green Mountain Rock Climbing Center are located nearby. Discover genuine guest reviews for Cozy 1850s home on the riverfront with mountain & river views - dog-friendly along with the latest prices and availability – book now.
Fireplace
Pet friendly
Don't see what you're looking for?
See all available properties in Woodstock
View all properties
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 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 Marsh-Billings-Rockefeller National Historical Park

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
Image for Woodstock Town Hall Theatre

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?
Prepare to be pleasantly surprised — you can find yourself in Woodstock for a mere . Allow Travelocity to save you time and money with our awesome vacation packages. With flights, hotels and tours all ready to go at our one-stop shop, what’s stopping you?
How long should my Woodstock vacation be?
Your Woodstock break can be as short or as long as you’d like it to be, but the majority of people stay about 2 nights. Hoping to venture off the beaten path and discover some lesser-known attractions? Stay an extra night or two and see another side of this place.
Where can I get the best vacation package deals for Woodstock?
It’s hard to top Travelocity when it comes to putting together your Woodstock package deal. There are as many as 400 air carriers and 1,000,000 properties worldwide to choose from. Plan your escape now and get ready to cross another exciting place off your bucket list.
Why should I book my Woodstock vacation bundle with Travelocity?
From exciting destinations to fun experiences, we have everything you need to satisfy your love for travel. Our 24/7 customer support will also make sure you’re taken care of before, during and after your trip. And don’t fret if you spot a cheaper price on your reservation, we’ll match it. That’s our Price Match Guarantee.
Can I save on my Woodstock car rental if I book it with hotels and flights?
You most certainly can — combine your car, hotel and flight into a Woodstock vacation package and you’ll save a ton. With so much to discover in Woodstock, having your own wheels will more than come in handy. Once you’ve settled into the driver’s seat, put the stereo on and cruise toward Fenway Park, a top sight about 110 mi from Woodstock.
What is the best time of year to go to Woodstock?
You can swerve the tourist masses and save money in July, November and December, the quietest period for tourist visits. The peak season months of January, June and August are livelier (and pricier), but there’ll be more events on around Woodstock. Reserve a hotel in and you’ll get the best value for your dollar. As a rule, room rates are higher in .
Which airport is best for Woodstock?
One of your best options is Lebanon Municipal Airport (LEB), 11 mi east of the hustle and bustle of downtown Woodstock. Another choice is Rutland Southern Vermont Regional Airport (RUT), 20 mi away from central Woodstock).
What is there to do in Woodstock?
Woodstock is brimming with things to see and do, like Billings Farm and Museum and Marsh-Billings-Rockefeller National Historical Park. These well-known attractions are on most people’s travel itineraries.
Where should I stay when visiting Woodstock?
Many visitors choose to spend their nights at the The Shire Woodstock. It’s an excellent base for your Woodstock vacation.