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

A wooden covered bridge with a sign reading 'Slippery When Wet' and a sign above the entrance that says 'Michael's Bridge.'
FlightsFlightsHotelsHotels

Woodstock

Woodstock

Top Windsor County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was CA $1,473, price is now CA $1,345 per person
CA $1,345
per person
Dec 29 - Jan 3
found 11 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Rutland (RUT)
9.4/10 Exceptional! (608 reviews)

The Landgrove

The Landgrove

3.5 out of 5
Price was CA $2,287, price is now CA $2,025 per person
CA $2,025
per person
Dec 29 - Jan 3
found 11 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Rutland (RUT)
9.4/10 Exceptional! (13 reviews)
The Inn is in a beautiful setting. The staff were very friendly and helpful. My room was spacious and a comfortable arm chair and good lamp provided a cozy place for R&R. The spacious common area & well kept grounds would be a very pleasant place to spend time with family and friends. I was advised in advance that the restaurant was not serving dinner, but the staff provided a list of eateries in the local area. I had a very good meal at the New American Grill. The breakfast menu at the hotel was refreshing and the food was VERY good. I thoroughly enjoyed my stay and would highly recommend the inn especially to those who enjoy the atmosphere of well kept historical structures.

Reviewed on Oct 29, 2026

The Vesper

The Vesper

3 out of 5
Price was CA $1,886, price is now CA $1,691 per person
CA $1,691
per person
Dec 29 - Jan 3
found 11 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Springfield (VSF)
9.2/10 Wonderful! (82 reviews)
Very cute spot, good location and staff is super nice:)

Reviewed on Nov 2, 2026

Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
Price was CA $1,568, price is now CA $1,424 per person
CA $1,424
per person
Dec 29 - Jan 3
found 11 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Rutland (RUT)
10/10 Exceptional! (38 reviews)

Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was CA $1,642, price is now CA $1,513 per person
CA $1,513
per person
Dec 29 - Jan 3
found 11 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Springfield (VSF)
8.6/10 Excellent! (1,011 reviews)

Windsor County Hotel Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is CA $465 per night from Nov 30 to Dec 1
CA $465
CA $573 total
Nov 30 - Dec 1
includes taxes & fees
9.4/10 Exceptional! (629 reviews)
"Fantastic stay at Woodstock Inn this week! The room and property were spotless, and the staff was incredibly kind and welcoming. The spa was beautiful, the food at Red Rooster was excellent, and the athletic center, pool, and hot tub were all great. The entire property has a quiet, peaceful atmosphere ..."

Reviewed on Nov 6, 2026

Woodstock Inn & Resort
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
111 Jackson Gore Road Ludlow VT
Fully refundableReserve now, pay when you stay
The price is CA $261 per night from Nov 18 to Nov 19
CA $261
CA $317 total
Nov 18 - Nov 19
includes taxes & fees
Jackson Gore Village, A Vail Resorts Property
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
The price is CA $231 per night from Nov 29 to Nov 30
CA $231
CA $282 total
Nov 29 - Nov 30
includes taxes & fees
On The River Inn
See all 1,388 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $1,345. 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

A snow-covered ski resort with ski lifts, buildings, and a mountain backdrop.

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.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.