Book Exclusive Windsor Vacation Packages

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Windsor flight + hotel packages

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Mountain Lodge at Okemo

Mountain Lodge at Okemo

3 out of 5
Clock Tower Base Area
per person
Oct 12 - Oct 17
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
Stay at this 3-star ski hotel in Ludlow. Enjoy free WiFi, free parking, and a free area shuttle. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.
Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Clock Tower Base Area
per person
Oct 12 - Oct 17
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
Stay at this 4-star ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.
Winterplace at Okemo

Winterplace at Okemo

4 out of 5
Clock Tower Base Area
per person
Oct 12 - Oct 17
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
Stay at this 4-star ski aparthotel in Ludlow. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Okemo Mountain Resort and Snow Stars Carpet are located nearby.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
per person
Oct 12 - Oct 17
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
Stay at this 3-star spa hotel in Ludlow. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Jackson Gore Parking are located nearby.
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
per person
Oct 12 - Oct 17
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
Stay at this 3-star spa resort in West Dover. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Mount Snow and Ego Alley Ski Lift are located nearby.

Top Windsor hotels deals

White River Inn and Suites

White River Inn and Suites

2.5 out of 5
91 Ballardvale Drive, White River Junction, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $164 per night
CA $164
CA $181 total
Sep 7 - Sep 8
includes taxes & fees
Book a stay at this business-friendly hotel in White River Junction. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Upper Valley Aquatic Center and Briggs Opera House are located nearby.
Pool
Breakfast included
Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

2.5 out of 5
25 Airport Road, West Lebanon, NH
Free cancellation
Reserve now, pay when you stay
The price is CA $187 per night
CA $187
CA $233 total
Aug 24 - Aug 25
includes taxes & fees
Book a stay at this business-friendly hotel in West Lebanon. Enjoy free WiFi, free parking, and room service. Our guests praise the breakfast and the pool in our reviews. Popular attractions New England Transportation Institute and Museum and Briggs Opera House are located nearby.
Pool
Hot tub
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is CA $565 per night
CA $565
CA $683 total
Sep 1 - Sep 2
includes taxes & fees
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Middle Covered Bridge and Woodstock Town Hall Theatre are located nearby.
Pool
Hot tub
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Free cancellation
Reserve now, pay when you stay
Get rates
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
Pet-friendly
Parking included
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd, Quechee, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $164 per night
CA $164
CA $181 total
Aug 24 - Aug 25
includes taxes & fees
Book a stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Quechee Gorge Bridge and Quechee Gorge Village are located nearby.
Pool
Breakfast included
Super 8 by Wyndham White River Junction

Super 8 by Wyndham White River Junction

2 out of 5
442 North Hartland Rd, I-91 Exit 11 Rt 5 S 1/4 Mile, White River Junction, VT
The price is CA $116 per night
CA $116
CA $128 total
Aug 31 - Sep 1
includes taxes & fees
Book a stay at this business-friendly motel in White River Junction. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Upper Valley Aquatic Center and Briggs Opera House are located nearby.
Breakfast included
Pet-friendly
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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.

Popular places to visit

Harpoon Brewery

You can take time to visit Harpoon Brewery during your travels to Windsor. Wander the forest or discover the area's mountain views.

Harpoon Brewery

Mt Ascutney Hospital and Health Center: Primary Care - Windsor

Though Mt Ascutney Hospital and Health Center: Primary Care - Windsor might be what brings you to town, perhaps you'll have a chance to explore more of Windsor while you are here.

Mt Ascutney Hospital and Health Center: Primary Care - Windsor

American Precision Museum

You can spend time exploring the galleries in American Precision Museum in Windsor. Wander the riverfront in this quaint area.

American Precision Museum

Windsor Vacations

It's always handy to know a little about your destination before you set off on your escape. Put a mark near Windsor on your map now and start planning for your big adventure!

Windsor is 110 miles (177 kilometers) to the northwest of Boston, a prominent city.

It's an area of Central Vermont- Killington that approximately 2,000 people reside in.

Hotels in Windsor

Traveling to Windsor? Don't wait until the last minute to book one of its 5 available accommodations. Once you've made up your mind, all that’s left is the fun part — actually being there!

The Snapdragon Inn and Kedron Valley Inn are some of Travelocity's top accommodation options in Windsor.

Places to visit in Windsor

Spending time in nature is proven to positively affect both your emotional and physical state of being. Spend time at Mt Ascutney State Park and feel the benefits of connecting with our natural environment. Want more options? Few things give us a peek into bygone days quite like old buildings. Why not take a tour around Old Constitution House and hear a few anecdotes about what went on behind closed doors? But there's more. There is no better teacher than history. Travel back through time for an interesting lesson at Saint-Gaudens National Historic Site.

Where do you fly into for Windsor?

There's nothing more exciting than finally hitting the tarmac in a totally new place. If you're going to Windsor, chances are you'll be disembarking at Lebanon Municipal Airport (LEB). It's about 11 miles (18 kilometers) to the northeast of the downtown area. Pick up your suitcase and get ready to kick-start your adventure!

Frequently asked questions

How much are vacation packages to Windsor?
Travelocity offers flight and hotel vacation packages starting as low as CA $1,128. With such great deals, you'll be exploring all of Windsor in the blink of an eye.
How long should my Windsor vacation be?
Generally, 2 nights is what many tourists book for their Windsor vacation. That's a rough guide, but there's loads more to discover if you give yourself a little more time.
Where can I get the best vacation package deals for Windsor?
Landing an unbeatable package deal to Windsor is a cinch with Travelocity. With as many as 400 air carriers and 1,000,000 properties all over the world, you're spoiled for choice when it comes to selecting your hotels and flights.
Why should I book my Windsor vacation package via Travelocity?
With first-rate service, customer support available 24/7 and some of the most idyllic escapes money can buy, you'll never roam alone. And if you find a lower price, we'll match it. That's our Price Match Guarantee.
Can I save money on my Windsor car rental if I bundle it with a hotel or flight?
With a Windsor vacation package, you can bundle your flight, car and hotel bookings and save a tidy sum. If you'd love to explore the best of this wonderful part of the world, why not make a beeline for Fenway Park? This must-see attraction is 161 kilometers from Windsor. With your own set of wheels, you'll be there in no time.
Which airport is best for Windsor?
Manchester-Boston Regional Airport (MHT) is 97 kilometers from the city center and is the starting point for many unforgettable experiences. Alternatively, Lebanon Municipal Airport (LEB) is 18 kilometers away from central Windsor and Rutland Southern Vermont Regional Airport (RUT) is 48 kilometers away from central Windsor.
What is there to do in Windsor?
While venturing off the beaten track is rewarding, you shouldn't miss the big-name attractions that make a place famous. Harpoon Brewery and The Sustainable Farmer are just two of them in Windsor.
Where should I stay when visiting Windsor?
If you're after somewhere to lay your head, check out the Windsor Mansion Inn. It's the top pick for many visitors.

Photos of local treasures

Browse Windsor vacation photos for more inspiration

Photo by William E Berry Jr.
Photo by William E Berry Jr.
Photo by mike dobias
Photo by mike dobias