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 Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is S$517 per night from 16 Dec to 17 Dec
S$517
includes taxes & fees
16 Dec - 17 Dec
9.2/10 Wonderful! (483 reviews)
"The overall experience was great."

Reviewed on 20 Nov,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 S$279 per night from 26 Nov to 27 Nov
S$279
includes taxes & fees
26 Nov - 27 Nov
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 15 Nov,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 S$170 per night from 25 Nov to 26 Nov
S$170
includes taxes & fees
25 Nov - 26 Nov
9.6/10 Exceptional! (422 reviews)
"Clean, easy, convenient and funky!"

Reviewed on 23 Nov,2024

Sleep Woodstock Motel
See all 2,456 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?
Much less than you might think — from a low , in fact! By combining flights, hotels and car rentals into a custom-built holiday 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 holiday 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 travellers 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 holiday?
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. Holidaying 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 organising a wilderness getaway in a cabin or want to stay in a cosy apartment in the city, Expedia will help make it happen.
Can I choose my airline with a Woodstock Expedia holiday 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 travelling style.
If I'm not able to travel, can I cancel my Woodstock holiday package?
Yes you can, and we’ll help you every step of the way. You may be able to change or cancel your Woodstock holiday 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.

Popular places to visit

Saskadena Six Ski Area

Hit the slopes in Woodstock with a visit to Saskadena Six Ski Area. Wander the riverfront in this quaint area.

Saskadena Six Ski Area

Red Wagon Toy Company

Enjoy an outing to Red Wagon Toy Company during your stay in Woodstock. Wander the riverfront in this quaint area.

Red Wagon Toy Company

* 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.