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

Aerial view of the Connecticut River snaking through a vibrant tapestry of fall foliage near a golf course and lake, White River Junction, Vermont, United States.
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White River Junction

White River Junction

Top Windsor County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!

3 out of 5
Price was CA $4,927, price is now CA $4,623 per person
CA $4,623
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Rutland (RUT)
9.8/10 Exceptional! (17 reviews)
We loved our visit here. John and Yvonne were wonderful. The space was clean, quiet, and truly magical. The views were second to none and the castle and other buildings are truly worth experiencing. We loved learning about the history of this place and we will certainly be back.

Reviewed on Jan 18, 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 $152 per night from May 17 to May 18
CA $152
CA $168 total
May 17 - May 18
includes taxes & fees
9.4/10 Exceptional! (1,189 reviews)
The breakfast was basic. There were prepackaged egg biscuits, a waffle maker, oatmeal to make yourself, hard boiled eggs, cereal, and pastries. The room was clean. The beds were comfortable, but the pillows were not. For a two-star motel, it is very good.

Reviewed on May 11, 2026

Align Inn Vermont
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is CA $436 per night from May 25 to May 26
CA $436
CA $540 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (576 reviews)
Everything was excellent

Reviewed on May 5, 2026

Woodstock Inn & Resort
Hotel Coolidge

Hotel Coolidge

3 out of 5
39 South Main Street White River Junction VT
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from May 17 to May 18
CA $144
CA $159 total
May 17 - May 18
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
My husband and I have stayed overnight at the Hotel Coolidge on many occasions. It is conveniently located near Dartmouth-Hitchcock Medical Center. The owner and staff are always friendly, the rooms are clean, the beds are comfortable, coffee and tea are provided around the clock in the lobby, there ...

Reviewed on Apr 30, 2026

Hotel Coolidge
See all 1,368 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 $4,623. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.