New York State may have travel restrictions in place, including self-quarantine, due to COVID-19.

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Woodstock Vacation Packages

Choose two or more items and save on your trip:

Woodstock Vacation: Coronavirus Information

Most Woodstock hotels offer free cancellation. Consider booking refundable hotels rather than non-refundable ones. Just look for the ‘free cancellation’ message during your hotel search. Prices can vary, but right now we believe that flexibility matters.

For more information about the impact of COVID-19 on your Woodstock trip, please visit our Coronavirus Information page (opens in new window).

Top Woodstock Flight + Hotel Deals

The Manchester View - Near Manchester Designer Outlets
Wilburton Inn
Four Winds Country Motel
Hilton Garden Inn Albany Airport
Paradise Inn
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2021 Woodstock vacation deals

Hilton Garden Inn Albany Airport
Ramada Plaza by Wyndham Albany
Fairfield Inn by Marriott Albany University Area
TownePlace Suites by Marriott Albany Downtown/Medical Center
Cocca's Inn & Suites Wolf Rd, Albany Airport
Don't see what you're looking for?
See all available trips from Ashburn to Woodstock

Top Hotels in Woodstock

The Woodstock Inn on the Millstream
The Woodstock Inn on the Millstream
3 out of 5
48 Tannery Brook Rd, Woodstock, NY
The price is $155 per night from Nov 4 to Nov 5
4.4/5Wonderful! (65 reviews)

"Property was nice and proximity to Main Street was ideal. Could have used more supplies such as bar soap, hand sanitizer. Pocket door to bathroom was sketchy and was annoying to open and close."…"

Reviewed on Aug 30, 2020

The Woodstock Inn on the Millstream
Twin Gables of Woodstock
Twin Gables of Woodstock
2.5 out of 5
73 Tinker St, Woodstock, NY
Free CancellationReserve now, pay when you stay
The price is $149 per night from Oct 26 to Oct 27
4.8/5Exceptional! (5 reviews)

"The staff went above and beyond making us feel welcome and at home! Very clean, cozy, and a very short walk to all of the best Woodstock shopping, restaurants, and bars."…"

Reviewed on Oct 19, 2020

Twin Gables of Woodstock
Hotel Woodstock - Queen Anne's Lace Suite
Hotel Woodstock - Queen Anne's Lace Suite
Woodstock, NY
The price is $59 per night from Oct 29 to Oct 30
4.7/5Exceptional! (15 reviews)
Cool hotel in the center of town

"This hotel is old, small + very vibey..with all the important details, good hot water, comfy bed + downstairs is the best food, lattes in Woodstock! There's a small outdoor porch off the room that looks out at the mountains for morning coffee and the room is super quiet, we're already planning the ..."…"

Reviewed on Oct 25, 2019

Hotel Woodstock - Queen Anne's Lace Suite
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.

Top things to do in Woodstock

A Unique Lifecasting Experience in Woodstock
Image for A Unique Lifecasting Experience in Woodstock

A Unique Lifecasting Experience in Woodstock

Per adult
Llama/Alpaca Hike and Farm Tour
Image for Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

Per adult
Indoor Golf Simulator Experience in Windham
Image for Indoor Golf Simulator Experience in Windham

Indoor Golf Simulator Experience in Windham

Per adult

What are the advantages of a road trip to Woodstock?

There’s nothing quite like a Woodstock road trip. And Expedia makes it easy for you to turn all those road trip ideas into reality. You can find cheap deals on hotels in Woodstock or bundle your hotels with car rentals to save even more. With our Woodstock packages, you’ll find hitting the highway for that road trip adventure is more affordable than ever.  

How to plan a road trip to Woodstock?

Planning a road trip can feel daunting, especially when you’ll be making multiple bookings for your itinerary. But you can find car rentals in Woodstock and low rates on hotels all in one place— Expedia. How you plan your road trip depends on what’s important to you. People love to take road trips to experience the great outdoors, bond with friends or family and see more of the world. When planning, bundle your car rental and hotel into one discounted package to maximize savings on both. Or, leave room for spontaneity, booking what you need when you need it with our last-minute deals.  

What to do on a road trip to Woodstock?

When taking a road trip adventure, it’s best to plan how you want to spend your time on your road trip itinerary. We don’t want you to miss out on any of the best things to do in Woodstock. You can book all the road trip activities on your Woodstock wishlist, and even plan activities along your route as well.  

How to rent a car for a road trip?

For an epic road trip, you'll need the perfect car. Renting a car for a road trip is the best option that doesn’t put miles or strain on your vehicle, and especially when it's also so affordable. Because when you book on Expedia, it doesn't need to be expensive. You can pick up a cheap car rental and head out to one of these incredible vacation rentals in Woodstock. And when you bundle car rentals with hotel stays, you'll save even more on each part of your journey.

Frequently asked questions

How much does a Woodstock vacation package cost?
Starting from an incredible $341, you can tailor your Woodstock vacation package. Simply bundle flights, hotels and car rentals and we’ll reward you with discounts.
If I'm not able to travel, can I cancel my Woodstock vacation package?
If you’ve booked a Woodstock vacation package, you can amend or cancel it, but there may be a charge in some circumstances. You may be able to cancel and rebook at no cost if you’ve locked in your package in the last 24 hours. If it’s been more than that, you may be charged a fee by your hotel, airline or car rental company. If you suddenly need to change your plans, make our Customer Service Portal your first stop for more information.
How do I get a cheap travel package to Woodstock?
Our Woodstock vacation packages offer plenty of savings for the savvy wanderer. How does as much as $583 sound? That’s what you could save if you combine your hotel, flights and rental cars into a convenient package. But great bargains are only the start of your next memorable adventure. When you book with Expedia, and you’ll have over 550 air carriers and 1,000,000 hotels all over the world to select from. No matter your style or budget, there’s a vacation package to suit you.
Where should I stay in Woodstock?
With loads to explore in Woodstock, it’d be handy for you to secure a room in a hotel near its attractions. Karma Triyana Dharmachakra Monastery, Woodstock Golf Club and Woodstock Public Library are some interesting ones to put on your must-see list.
What are the top hotels in Woodstock?
Make a reservation at Hotel Dylan. It’s one of this area’s most popular properties. Another well-known option in Woodstock is The Woodstock Inn on the Millstream.
When is the best time of year to visit Woodstock?
You’ll need to consider your priorities to find the right answer. Typically, you’ll score the best deals in , while is when prices are at their highest. Woodstock draws the crowds in . If you’re in the mood for a more relaxed getaway, would be a better time to pack your bags.
How far in advance should I book my Woodstock vacation?
It can be hard to know when the best time is to book your vacation to Woodstock. But usually the earlier you book, the better the prices. In some cases, you can reserve your flights and hotels nearly 12 months before departure. If you’re thinking of a last-minute getaway, no need to fret! There are incredible deals advertised on Expedia every single day.
What does an Expedia Woodstock travel package include?
Hotels, flights and rental cars — we’ve got them covered. With Expedia, you can shape your Woodstock package just the way you want. All you have to do is decide what you need. Once you’ve made your booking, you can add on fun things like tours and activities. The more you bundle, the more you save!
What should I know before booking a Woodstock travel package?
You can look forward to saving with an Expedia travel package. Combine your flights, rental cars and hotels and enjoy fantastic discounts. You’re not restricted to hotels, however. Book with us and choose from oceanfront condos, creek-side mountain cabins and just about everything in between!
Does Expedia offer Book Now, Pay Later Woodstock vacation packages?
If you’re aching to see the world but aren’t able to cough up the dough, Expedia can assist with a custom payment plan. Thanks to our partnership with online lender Affirm, you can Book Now, Pay Later and start planning your journey today.
Can I choose my airline with a Woodstock Expedia vacation package?
Yes — that’s the beauty of an Expedia package. You’re in control. We have access to more than 550 partner airlines around the world, so you have lots of choice when creating your Woodstock trip.