Windsor County Holidays from AU$1,121

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Your Windsor County Holiday

With a Windsor County holiday package, you can forget about planning hassles and instead focus on experiencing everything this exciting destination has on offer. Begin your trip to Windsor County with some time exploring Ludlow visiting popular sights like Weston Playhouse and Lake Rescue. Norwich is another top city that lures crowds from near and far. Quechee Gorge Bridge and Quechee Gorge Village are two of the leading places to see in this destination. From the instant you book your Windsor County holiday to the second you come back home, Expedia will take care of you each step of the way.

Top destinations in Windsor County

Ludlow which includes street scenes
FlightsFlightsHotelsHotels

Ludlow

Ludlow

The Latest Windsor County Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain

2.5 out of 5
Price was AU$1,205, price is now AU$1,121 per person
AU$1,121
per person
11 Oct - 13 Oct
found 1 day ago
Return direct flight included
Los Angeles (LAX) to Rutland (RUT)
8.4/10 Very Good! (655 reviews)
room was clean, a/c worked well. had dinner there at The Red Slate Restaurant - waited over an hour for 2 hot sandwiches. would not recommend eating there.

Reviewed on 30 Aug. 2025

Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Price was AU$2,083, price is now AU$1,730 per person
AU$1,730
per person
11 Oct - 13 Oct
found 1 day ago
Return direct flight included
Los Angeles (LAX) to Springfield (VSF)
9.6/10 Exceptional! (62 reviews)
Oz was a wonderful host. He was attentive and a delight to chat with. The room was very nice and we slept well. The shower is tiny, but this was not an inconvenience. We did have a bit of a problem with dining in the area. So many restaurants are closed on days during the week. We were told this is because right now there isn't enough business for them to be open because this area is really built around the skiing season. We enjoyed ourselves. Thanks, Oz!

Reviewed on 30 Aug. 2025

Mountaineer Inn

Mountaineer Inn

2 out of 5
Price was AU$1,243, price is now AU$1,129 per person
AU$1,129
per person
11 Oct - 13 Oct
found 1 day ago
Return direct flight included
Los Angeles (LAX) to Springfield (VSF)
8.8/10 Excellent! (501 reviews)
Easy in and out. All transactions with this property are handled online; there was no person-to-person interaction while on the site. The rooms and bathrooms were clean, and the beds were comfortable. We'd consider this again in the future.

Reviewed on 23 Aug. 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was AU$1,580, price is now AU$1,439 per person
AU$1,439
per person
11 Oct - 13 Oct
found 1 day ago
Return direct flight included
Los Angeles (LAX) to Rutland (RUT)
8.6/10 Excellent! (1,006 reviews)
The Inn is located in the Green Mountains at Killington so at night you can open the windows and breathe the mountain air.

Reviewed on 26 Aug. 2025

The Engel House

The Engel House

3 out of 5
Price was AU$1,240, price is now AU$1,164 per person
AU$1,164
per person
11 Oct - 13 Oct
found 1 day ago
Return direct flight included
Los Angeles (LAX) to Rutland (RUT)
9.4/10 Exceptional! (13 reviews)
A very quaint property. The room was comfortable and clean.

Reviewed on 27 May 2025

Windsor County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rutland Southern Vermont Regional Airport (RUT)
Top Sights
Lake Rescue, Buttermilk Falls and Echo Lake

Our pick of the best Windsor County Hotel Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is AU$755 per night from 1 Sept to 2 Sept
AU$755
1 Sept - 2 Sept
includes taxes & fees
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
Get rates
The Shire Woodstock
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd, Quechee, VT
Fully refundableReserve now, pay when you stay
The price is AU$200 per night from 1 Sept to 2 Sept
AU$200
1 Sept - 2 Sept
includes taxes & fees
Align Inn Vermont
See all 1,316 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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 AU$1,121. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.