Windsor County Holidays
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Top hotels in Windsor County
Align Inn Vermont
5817 Woodstock Rd Quechee VT
S$164
10 Sept - 11 Sept
includes taxes & fees
9.4/10 Exceptional! (1,324 reviews)
"Room was nice but bathroom tub & faucet could use a little work. Staff was nice especially the first girl when we checked in."
Reviewed on 6 Sept, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
S$723
8 Sept - 9 Sept
includes taxes & fees
9.4/10 Exceptional! (602 reviews)
"Beautiful as is the town"
Reviewed on 3 Sept, 2026
The Jackson
43 Senior Lane Woodstock VT
S$241
9 Sept - 10 Sept
includes taxes & fees
9.6/10 Exceptional! (314 reviews)
"The inn and the grounds are beautifully maintained. The room was comfortable, and the restaurant on the premises was convenient but also had a great breakfast, well worth purchasing. The location was also great relative to downtown."
Reviewed on 6 Sept, 2026
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 1,000,000 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.
Stay near popular Windsor County attractions
Okemo Mountain Resort
9.2/10 (510 reviews)
Hit the slopes in Ludlow with a visit to Okemo Mountain Resort. Discover the mountain views in this romantic area.
Photo by Mike Gauthier
Quechee Gorge Bridge
9.2/10 (580 reviews)
Quechee Gorge Bridge is just one of the places to see in White River Junction, so why not enjoy the other things to explore during your travels? Wander the riverfront in this quaint area.
Photo by George Sykes
King Arthur Baking Company
9.4/10 (178 reviews)
You can enjoy retail therapy at King Arthur Baking Company during your stay in Norwich. While you're in the area, stroll along the riverfront.
Photo by Ed Gaffny
Quechee Gorge Village
9.0/10 (288 reviews)
You can search for that perfect souvenir at Quechee Gorge Village during your stay in Quechee. Amble around the area's riverfront or seek out the ski slopes.
Billings Farm and Museum
9.2/10 (84 reviews)
You can study the exhibits at Billings Farm and Museum, a museum with a storied past, during your travels to Woodstock. Wander the riverfront in this quaint area.
Photo by William E Berry Jr.
Mount Ascutney
8.8/10 (27 reviews)
Commune with nature and explore the great outdoors at Mount Ascutney during your travels in Brownsville. You can seek out the ski slopes while in the area.
Simon Pearce Mill
9.0/10 (80 reviews)
Learn about the local history of Quechee when you take a trip to Simon Pearce Mill. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.
What to do in Windsor County
Colonial Flintlock Musket Experience
S$164
per adult
100% of travellers recommend
* 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.
