Woodstock Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Woodstock

Woodstock Way Hotel
Woodstock Way Hotel
4 out of 5
10 Waterfall Way, Woodstock, NY
9.4/10 Exceptional! (121 reviews)
"Loved the property. A walk away from all the action. The staff was great and very helpful. We plan on returning again next Spring. Highly recommended."

Reviewed on 4 Nov,2024

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Woodstock Way Hotel
The Herwood Inn
The Herwood Inn
4.5 out of 5
148 Tinker St, Woodstock, NY
The price is S$324 per night from 3 Dec to 4 Dec
S$324
includes taxes & fees
3 Dec - 4 Dec
9.8/10 Exceptional! (44 reviews)
"Great place, great owners, would stay again/recommend to anyone."

Reviewed on 12 Nov,2024

The Herwood Inn
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 S$270 per night from 1 Dec to 2 Dec
S$270
includes taxes & fees
1 Dec - 2 Dec
8.8/10 Excellent! (175 reviews)
"Repeat guest & find quality continues to be worth our visit"

Reviewed on 11 Nov,2024

The Woodstock Inn on the Millstream
See all 2,288 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.

Frequently asked questions

How much does a Woodstock holiday package cost?
Our Woodstock holiday packages, which start from as low as , are the easiest way to save big bucks. Select your preferred hotels, flights and rental car to create a customized itinerary.
How do I get a cheap travel package to Woodstock?
Lock in flights that fit in with your schedule, add a hotel room to your booking and watch how much you save with a Woodstock holiday package. It’s as simple as that! From hotels and flights to rental cars and tours, Expedia is your gateway to cheap travel. And with more than 550 air carriers and 1,000,000 hotel options all over the world to select from, you won’t be short of choice.
Where should I stay in Woodstock?
Stay close to the action. Many people favor hotels in the vicinity of popular attractions, such as Overlook Mountain Trailhead, Karma Triyana Dharmachakra Monastery and Woodstock Music Shop.
What are the top hotels in Woodstock?
Twin Gables of Woodstock will be a perfect base for your Woodstock adventures. Situated in Zena, it’s one of the area’s top hotels.
How far in advance should I book my Woodstock holiday?
Be rewarded with the biggest variety and the cheapest prices by booking your Woodstock adventure nice and early. Airlines typically publish flights around 12 months prior to departure, so reserve your spot as soon as you can. That being said, Expedia is committed to providing you with the best deals around, so it’s always a good time to book your dream holiday!
What does an Expedia Woodstock travel package include?
It all comes down to what type of trip you’re contemplating. Woodstock travel deals can include car rentals, hotels and flights. You can mix and match to create the bundle that suits your style and budget. You can also add on activities and experiences after you’ve booked to score even bigger discounts.
What should I know before booking a Woodstock travel package?
You can save a tidy sum by bundling your airfares, hotels and rental cars. Once you’ve created your package, you can add on things like activities or tours. Your next awesome adventure is only a couple of clicks away.
Can I choose my airline with a Woodstock Expedia holiday package?
Definitely. Expedia has more than 550 partner airlines to pick from around the globe. With so many choices, finding the ideal carrier to whisk you off to Woodstock shouldn’t be hard.
If I'm not able to travel, can I cancel my Woodstock holiday package?
You sure can, and we’ll help you every step of the way. You may be able to cancel or amend your Woodstock holiday package at no cost within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company if your booking is older than that. If your circumstances unexpectedly change, have a look at our Customer Service Portal for further information.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.