Woodstock Holidays from £2,053

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Your Woodstock Holiday

Book a Woodstock holiday 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 holiday plans in motion!

Top Woodstock Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Shire Woodstock

The Shire Woodstock

3 out of 5
per person
14 Sept - 16 Sept
found 24 hours ago
Return flight included
London (LON) to Springfield (VSF)
8.8/10 Excellent! (772 reviews)
Liked the River. I will not stay here again. We drove from Bar Harbor, ME to the Shire. I found out yesterday that registration is only for two hours on Wednesday. We drove all day and arrived at 5:07 pm. Luckily the reception was still open. I had booked two rooms and only one room had a key in the room and had been registered for late arrival. What would have happened if they wouldn’t have been open. Then we found out no elevator and we had to lug everything upstairs. We had 2 weeks worth of clothes in suitcases so it was tough maneuvering the stairs.

Reviewed on 17 Jul 2025

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
per person
14 Sept - 16 Sept
found 24 hours ago
Return flight included
London (LON) to Springfield (VSF)
9.2/10 Wonderful! (521 reviews)
Really enjoyed our stay.

Reviewed on 18 Jul 2025

Stay At Jimmy's

Stay At Jimmy's

3 out of 5
per person
14 Sept - 16 Sept
found 24 hours ago
Return flight included
London (LON) to Springfield (VSF)
10/10 Exceptional! (34 reviews)
Superb stay in all ways!

Reviewed on 16 Jul 2025

Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
West Woodstock
per person
14 Sept - 16 Sept
found 24 hours ago
Return flight included
London (LON) to Springfield (VSF)
9.6/10 Exceptional! (15 reviews)
Lovely historic inn under new ownership. About 3 miles from woodstock center. Pretty spot right on the river. Smaller rooms expected in a inn that dates to 1760. Wxcellent aur conditioning. Breakfast was local breads, oatmeal, muffins, fruit, coffe. Would recommend ownership.

Reviewed on 19 Jul 2025

The Vesper

The Vesper

3 out of 5
per person
14 Sept - 16 Sept
found 24 hours ago
Return flight included
London (LON) to Springfield (VSF)
9.2/10 Wonderful! (24 reviews)
Charming quaint place with artistic decor. Care was taken with the breakfast - delicious, homemade and wonderful presentation. It felt very homey. Prompt response to my texts; excellent communication. Welcoming and friendly. I would definitely stay here again and recommend the Vesper highly.

Reviewed on 17 Jul 2025

Woodstock Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lebanon Municipal Airport (LEB)
Population
870
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Saskadena Six Ski Area, Montshire Museum of Science and Woodstock Town Hall Theatre

Top hotels in Woodstock

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is £401 per night from 17 Aug to 18 Aug
£401
17 Aug - 18 Aug
includes taxes & fees
9.2/10 Wonderful! (527 reviews)
"Really enjoyed our stay."

Reviewed on 18 Jul 2025

Woodstock Inn & Resort
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road, Woodstock, VT
The price is £207 per night from 22 Jul to 23 Jul
£207
22 Jul - 23 Jul
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"Helpfulness of the staff was first class"

Reviewed on 13 Jul 2025

On The River Inn
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 £115 per night from 30 Jul to 31 Jul
£115
30 Jul - 31 Jul
includes taxes & fees
8.6/10 Excellent! (779 reviews)
"The property offers close walking distance to shops and restaurants, easy access to a grocery store, and a gorgeous view of the ŕiver."

Reviewed on 17 Jul 2025

The Shire Woodstock
See all 2,637 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 Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

What to do in Woodstock

Signature Vermont Wayfinders Private Guided Tour

Signature Vermont Wayfinders Private Guided Tour

£585
per traveller
Signature Vermont Wayfinders Private Guided Tour
See all activities in Woodstock

Frequently asked questions

How much does a Woodstock travel package cost?
Choose from any combination of car rentals, flights and hotels, and you can be holidaying in Woodstock from just £2,053. And the more you bundle, the more dollars you save. The getaway of your dreams has never been more affordable.
If I'm not able to travel, can I cancel my Woodstock travel package?
You can cancel your Woodstock booking if your plans have been upended. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. It may be possible to change or cancel free of charge if you booked in the last 24 hours. Visit our Customer Service Portal for more information.
How do I get a cheap travel package to Woodstock?
Bundling your hotel and flight with Expedia won't just save precious time — it'll save you a few dollars too. A Woodstock travel package makes it simple to put together your perfect trip. With more than 550 airlines around the world to pick from, finding convenient flights that suit your busy schedule won't be hard. On top of that, we've got over 1,000,000 hotel options globally to choose from. Now that's what we call choice. No matter who you are, Expedia will help show you the world.
Does Expedia offer Book Now, Pay Later Woodstock holidays?
Yes, we do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply choose the payment plan best suited to your needs during the checkout process and take away the stress of budgeting for your trip. Don't forget to bundle your accommodation, flights and activities with Expedia to get the biggest bang for your buck. Browse our flexible payment options below:

  • Pay monthly holidays: If paying bite-sized amounts each month is something that would work for you, Klarna offers just that! Paying in easy monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: If you'd prefer to pay for your escape in multiple transactions, holidays paid in instalments might be the right option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Clicking on the "book now" button is much easier with this option. Just put down a small deposit on your holiday and then start packing your suitcase.

Where should I stay in Woodstock?
With interesting attractions such as Woodstock Country Club and Suicide Six Ski Area in this area, look for a hotel located near them. Woodstock Town Hall Theatre is another sight in Woodstock that draws in the crowds.
What are the top hotels in Woodstock?
White River Inn and Suites and Hotel Coolidge are a couple of the most well-known hotels in Woodstock. Why not check out the facilities and rates at each and then make a decision?
How far in advance should I book my Woodstock holiday?
While not all air carriers advertise ticket prices early, it's usually possible to look up international airfares on Expedia up to 12 months in advance. This is the time when you'll score some incredible deals. If you've left everything to the last minute, you may still be in luck. Sometimes the lowest prices become available a few weeks before departure.
What does an Expedia Woodstock travel package include?
Expedia has everything you need to organise your Woodstock getaway, but how your package is structured is totally up to you. Select from any combination of hotels, rental cars and flights. In search of some tours or activities to fill in your time? Once you've made your booking, you can add them too. No matter your style or budget, there's a deal to meet your needs.
What should I know before booking a Woodstock travel package?
Our prices are always low. However, you'll pick up even more savings when you book your hotels, flights and car rentals together. With an Expedia package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Woodstock Expedia travel package?
Yes — that's one of the best things about an Expedia travel package. You're in charge! We have access to more than 550 airline partners throughout the world, so you have options galore when planning your Woodstock trip.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.