Woodstock Vacation Packages

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Your Woodstock Vacation

Book a Woodstock vacation package and get ready for a thrilling adventure. Known for its artistic creativity and lively atmosphere, there's plenty to keep you on the move in this city. A trip to Woodstock is a superb opportunity to sightsee. Check out renowned attractions like Saskadena Six Ski Area, Billings Farm and Museum and Sugarbush Farm. Stop dreaming and start adventuring. Explore the multitude of options on Expedia today and finally put your Woodstock vacation plans in motion!

Top Woodstock Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
per person
Jan. 10 - Jan. 17
found 10 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Springfield (VSF)
9.8/10 Exceptional! (27 reviews)
The deer valley inn was a cozy small guesthouse . The staff were very kind and helpful. Highly recommend the place . The staff manager was originally from turkey. Really sorry I forgot the name at this moment but he was wonderful .

Reviewed on Oct. 15, 2024

Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
Clock Tower Base Area
Save 100% on your flight
per person
Jan. 10 - Jan. 17
found 10 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Springfield (VSF)
7.6/10 Good! (26 reviews)
I had an amazing time with my family, I will definitely be coming back

Reviewed on Jul. 29, 2024

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Save 100% on your flight
per person
Jan. 10 - Jan. 17
found 10 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Springfield (VSF)
8.6/10 Excellent! (682 reviews)
We loved this resort!

Reviewed on Nov. 10, 2024

Mountain Lodge at Okemo

Mountain Lodge at Okemo

3 out of 5
Clock Tower Base Area
Save 100% on your flight
per person
Jan. 10 - Jan. 17
found 10 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Springfield (VSF)
8/10 Very Good! (194 reviews)
Staff in the restaurant were exceptional as was reception. As a single traveller the restaurant went out of the way to accommodate me. The receptionist aided me in accessing the locked coffee area.

Reviewed on Oct. 13, 2024

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
per person
Jan. 10 - Jan. 17
found 10 hours ago
Roundtrip non-stop flight included
Québec (YQB) to Springfield (VSF)
8.8/10 Excellent! (150 reviews)
The staff were extremely friendly and helpful in the surrounding area. Tons of great food and shopping, and beautiful views - would absolutely recommend this place to stay in Vermont !

Reviewed on Nov. 17, 2024

Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.
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Woodstock Hotel Deals

Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is CA $432 per night from Dec. 16 to Dec. 17
CA $432
CA $537 total
includes taxes & fees
Dec 16 - Dec 17
9.2/10 Wonderful! (483 reviews)
"The overall experience was great."

Reviewed on Nov. 20, 2024

Woodstock Inn & Resort
The Shire Woodstock
The Shire Woodstock
3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
The price is CA $243 per night from Nov. 27 to Nov. 28
CA $243
CA $298 total
includes taxes & fees
Nov 27 - Nov 28
8.6/10 Excellent! (681 reviews)
"The room was surprisingly clean and modern and the view out the back door towards the river and the hills across the river was awesome. The location was great: it was a short walk to downtown. All good."

Reviewed on Nov. 15, 2024

The Shire Woodstock
Sleep Woodstock Motel
Sleep Woodstock Motel
2 out of 5
4324 West Woodstock Road, Woodstock, VT
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Nov. 25 to Nov. 26
CA $161
CA $177 total
includes taxes & fees
Nov 25 - Nov 26
9.6/10 Exceptional! (421 reviews)
"friendly staff"

Reviewed on Nov. 18, 2024

Sleep Woodstock Motel
See all 2,451 properties in Woodstock
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Woodstock vacation package cost?
Much less than you might think — from a low CA $1,464, in fact! By combining flights, hotels and car rentals into a custom-built vacation package, your trip to Woodstock is just clicks away.
How do I get a cheap travel package to Woodstock?
Browse and book everything in the one place with our Woodstock vacation packages. You’ll find deals on flights, hotels and more that’ll keep your credit card happy and adventurous side satisfied. And, with more than 550 partner airlines and 1,000,000 properties all over the world to choose from, you’ll have the flexibility to mix and match as you like.
Where should I stay in Woodstock?
Stay where the action is. Many travelers favor hotels around top sights, like Billings Farm and Museum, Saskadena Six Ski Area and Marsh-Billings-Rockefeller National Historical Park.
What are the top hotels in Woodstock?
Get your trip off to a flying start by booking a stay at The Blue Horse Inn. It’s one of most popular properties in Woodstock. Another option is Historic Ski Lodge On 112 - Acre Vineyard.
How far in advance should I book my Woodstock vacation?
Reserving your spot early with Expedia means one less thing to worry about. Many air carriers advertise tickets up to 12 months in advance. This is usually the cheapest time to book. If circumstances have left you booking late, great deals to Woodstock occasionally appear just a few weeks before departure.
What does an Expedia Woodstock travel package include?
From hotels and flights to car rentals, Expedia can help you craft a Woodstock package that’s ideal for you. Vacationing for a few weeks? Look into a hotel, flight and rental car bundle. If you’re taking a quick break, an airfare and hotel deal may suit you better. Experiences can also be added after you’ve booked. Our travel packages make it a breeze to plan and save.
What should I know before booking a Woodstock travel package?
When you book your hotels, flights and car rentals together, you’ll land incredible discounts. Whether you’re organizing a wilderness getaway in a cabin or want to stay in a cozy apartment in the city, Expedia will help make it happen.
Can I choose my airline with a Woodstock Expedia vacation package?
Yes, you can. Expedia has access to more than 550 partner airlines all over the world, so go with the carrier that best fits your budget and traveling style.
If I'm not able to travel, can I cancel my Woodstock vacation package?
Yes you can, and we’ll help you every step of the way. You may be able to change or cancel your Woodstock vacation package at no cost within 24 hours of booking. However, you may incur a fee from your airline, hotel or car rental company if your booking is older than that. If life throws you a curveball, take a look at our Customer Service Portal for more information.

Discover the most popular places to visit in Woodstock

Billings Farm and Museum

Billings Farm and Museum

5/5(1 review)

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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.