Windsor County Vacation Packages

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Your Windsor County Vacation

With a Windsor County vacation 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 vacation to the second you come back home, Expedia will take care of you each step of the way.

Top vacation destinations in Windsor County

FlightsFlightsHotelsHotels

Woodstock

Woodstock

Top Windsor County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was CA $1,144, price is now CA $1,095 per person
CA $1,095
per person
Jul 26 - Jul 28
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
8.6/10 Excellent! (274 reviews)
We had a great stay with our young children. We stayed in early summer. There were lots of outdoor trails for us to take advantage of during the day. The staff were all friendly and very helpful. The room was clean, quiet, and met all of our needs. We hope to be back!

Reviewed on Jun 19, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $1,187, price is now CA $1,119 per person
CA $1,119
per person
Jul 26 - Jul 28
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
8.8/10 Excellent! (935 reviews)
Beautiful setting. Under construction at the moment. Lovely fire pits along the river for evening gathering. Our room was newly renovated. Small but clean. But without storage: no bureau or closet or even a pole or place to hang clothes. Will be good to revisit once the restaurant is finished and hammering stops. Single Keurig in reception area for all the guests. Convenient grocery storage directly across the street. Lovely eateries and sites to visit within drive range. Interesting mix. I believe it is under new ownership and undergoing needed work before ski season.

Reviewed on Jun 22, 2026

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was CA $1,247, price is now CA $1,176 per person
CA $1,176
per person
Jul 26 - Jul 28
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Rutland (RUT)
8.8/10 Excellent! (1,001 reviews)
Amazing hot pool, great staff, another marvelous stay very close to the mountain and plenty of other activities. Laundry room is clutch (coin operated machines, change available at front desk). The wife had an injury and wasn't able to navigate stairs all that well, the front desk was understanding and were kind enough to move our room to the main floor, requiring no stairs, while the elevator was being worked on. New ownership is busy making some upgrades and maintenance and hopefully the vibes will remain the same as we've loved for years!

Reviewed on May 28, 2026

The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
Price was CA $1,193, price is now CA $1,138 per person
CA $1,138
per person
Jul 26 - Jul 28
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Rutland (RUT)
9/10 Wonderful! (1,003 reviews)
Fantastic place near everything you want to be near.

Reviewed on Jun 26, 2026

Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was CA $1,179, price is now CA $1,135 per person
CA $1,135
per person
Jul 26 - Jul 28
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
8.6/10 Excellent! (904 reviews)
Love the historical aspects of this place.

Reviewed on Jun 17, 2026

Windsor County Hotel Deals

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 CA $160 per night from Jun 28 to Jun 29
CA $160
CA $176 total
Jun 28 - Jun 29
includes taxes & fees
9.4/10 Exceptional! (1,227 reviews)
"The room was fine breakfast was fine"

Reviewed on Jun 23, 2026

Align Inn Vermont
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
9.4/10 Exceptional! (588 reviews)
"Had a short stay with my family to the Woodstock Inn and would love to return some day. Hospitality at its best in a beautiful town. The grounds and amenities were immaculate and authentic to the area. A memorable stay."

Reviewed on Jun 25, 2026

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Woodstock Inn & Resort
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
9.4/10 Exceptional! (1,006 reviews)
"It was beautiful, well designed with plenty of public gathering and relaxing places. The restaurant was excellent for both dinner and breakfast. We loved the coffee bars open all day. Great staff who were very professional and friendly!"

Reviewed on Jun 24, 2026

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On The River Inn
See all 1,338 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.
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Frequently asked questions

How much does a Windsor County vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Windsor County from just CA $1,095. And the more you bundle, the more cash you save. The vacation 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 vacation?
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 traveling 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 vacation 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 vacation package?
We get it — unexpected stuff happens. If you've locked in a Windsor County vacation 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

Ski resort in Vermont

Okemo Mountain Resort

9.2/5 (510 reviews)
Hit the slopes in Ludlow with a visit to Okemo Mountain Resort. Discover the mountain views in this quaint area.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.