Windsor County Holidays

Book a Hotel + Flight or Car together to unlock savings

Top destinations in Windsor County

Ludlow featuring street scenes
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Ludlow

Ludlow

Top hotels in Windsor County

The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (840 reviews)
"Had road view but was ok for the amount of time spent there. Located in perfect spot for easy walking to grocery store and downtown shopping. Hotel offers complimentary Coffee Bar, waters, cookies and even bicycles to ride"

Reviewed on 6 Oct 2025

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The Shire Woodstock
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is 10.773.060 ₫ per night from 10 Nov to 11 Nov
10.773.060 ₫
13.009.326 ₫ total
10 Nov - 11 Nov
includes taxes & fees
9.2/10 Wonderful! (536 reviews)
"Very nice property. Would love to visit again."

Reviewed on 7 Oct 2025

Woodstock Inn & Resort
Jackson Gore Village

Jackson Gore Village

3 out of 5
111 Jackson Gore Road, Ludlow, VT
Fully refundableReserve now, pay when you stay
The price is 4.614.202 ₫ per night from 10 Nov to 11 Nov
4.614.202 ₫
5.606.110 ₫ total
10 Nov - 11 Nov
includes taxes & fees
8.6/10 Excellent! (783 reviews)
"Beautiful area. Quiet and a friendly staff"

Reviewed on 6 Oct 2025

Jackson Gore Village
See all 1,317 properties in Windsor County
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 Windsor County holiday package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Windsor County from just . And the more you bundle, the more cash you save. The holiday of your dreams has never been more affordable.
How do I get a cheap travel package to Windsor County?
You'll save a ton of money if you bundle your hotels, car rentals and flights into a Windsor County travel package. Sometimes cheap packages mean fewer choices. But not with Expedia. We offer over 550 airlines and 1null000null000 hotels all over the world, which means you'll always have plenty of variety to choose from. Want to save even more? Add some exciting activities to your package deal to unlock even more bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Windsor County?
Okemo Mountain Resort is one of the key things that lures people to Windsor County, so it makes perfect sense that many decide to book their hotel in Ludlow.
What are the top hotels in Windsor County?
When it comes to hotels in Ludlow, Super 8 by Wyndham White River Junction and Holiday Inn Express Hotel & Suites White River Junction, an IHG Hotel are two terrific options. If you're spending time in Plymouth, Hotel Coolidge and White River Inn and Suites will make you feel right at home.
How far in advance should I book my Windsor County holiday?
It depends on the airline, but you can usually browse through international fares on Expedia up to a year in advance. While it's advisable to book ahead of time, lucky customers will sometimes find a cheaper flight only weeks before their intended journey.
What does an Expedia Windsor County travel package include?
It comes down to what you're looking for. If you're travelling by yourself, you might decide to bundle hotels and flights. Bringing the entire family to Windsor County? A travel package that includes hotels, rental cars and flights might suit you better. Expedia gives you the freedom and flexibility to tailor your travel package.
What should I know before booking a Windsor County travel package?
You'll save big with an Expedia travel package. Combine your flights, rental cars and hotels and be rewarded with great discounts. Hotels aren't your only choice, however. Book with us and take your pick of beachside condos, chalets in the middle of mountains and even glamping tents!
Can I choose my airline with a Windsor County Expedia holiday package?
Most definitely. Expedia has more than 550 partner airlines to select from across the world. With so many choices, finding the ideal carrier to fly you to Windsor County will be a snap.
If I'm not able to travel, can I cancel my Windsor County holiday package?
We get it — unexpected stuff happens. If you've locked in a Windsor County holiday package and need to amend or cancel it, we can help. It's always worth browsing our Customer Service Portal first for information. But generally, if you've booked your package within 24 hours, you may be able to amend or cancel your itinerary free of charge. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.