Book Exclusive Windsor Vacation Packages

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Windsor flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

3 out of 5
Price was CA $1,298, price is now CA $1,204 per person
CA $1,204
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Springfield (VSF)
Book a stay at this ski hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Snow and Heavy Metal Ski Lift are located nearby.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was CA $1,423, price is now CA $1,285 per person
CA $1,285
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was CA $1,359, price is now CA $1,265 per person
CA $1,265
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Springfield (VSF)
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and 2 hot tubs. Popular attractions Mount Snow and Tumbleweed Ski Lift are located nearby.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was CA $1,276, price is now CA $1,218 per person
CA $1,218
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
Price was CA $1,410, price is now CA $1,354 per person
CA $1,354
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.

Top Windsor hotels deals

Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
The price is CA $173 per night
CA $173
CA $190 total
Jul 13 - Jul 14
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.
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 $198 per night
CA $198
CA $215 total
Jul 19 - Jul 20
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 Quechee Gorge Bridge and King Arthur Baking Company are located nearby.
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
Free cancellation
Reserve now, pay when you stay
The price is CA $197 per night
CA $197
CA $217 total
Jul 14 - Jul 15
includes taxes & fees
Book a stay at this golf hotel in Killington. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is CA $652 per night
CA $652
CA $780 total
Jul 12 - Jul 13
includes taxes & fees
Book a stay at this 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 Quechee Gorge Bridge and Middle Covered Bridge are located nearby.
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
Free cancellation
Reserve now, pay when you stay
The price is CA $190 per night
CA $190
CA $220 total
Jul 13 - Jul 14
includes taxes & fees
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
Pool
Breakfast included
Holiday Inn Express Hotel & Suites White River Junction by IHG

Holiday Inn Express Hotel & Suites White River Junction by IHG

2.5 out of 5
121 Ballardvale Dr White River Junction VT
Free cancellation
The price is CA $243 per night
CA $243
CA $267 total
Aug 2 - Aug 3
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 breakfast and the helpful staff in our reviews. Popular attractions Quechee Gorge Bridge and King Arthur Baking Company are located nearby.
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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.

Stay near popular Windsor attractions

A snow-covered landscape with a wooden covered bridge over a river, surrounded by trees and a snowy path.

Brownsville Trail

9.4/10 (3 reviews)
You can take time to visit Brownsville Trail during your travels to Windsor. Discover the mountain views in this family-friendly area, or seek out the ski slopes.
See properties

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 $1,204. 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

A snow-covered river valley with a bridge and a town.
A covered bridge over a river with lush greenery and a clear sky.
A covered bridge with a sign that says "Walk your horses or pay two dollars fine."
A mountainous landscape with dense forests and a distant view of rolling hills.