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Top Windsor hotels deals

Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins

3 out of 5
122 Best Rd Windsor VT
The price is CA $322 per night
CA $322
CA $427 total
Sep 24 - Sep 25
includes taxes & fees
Stay at this cabin in Windsor. Enjoy free WiFi, free parking, and a garden. Popular attractions Hartland Public Library and Path of Life Garden are located nearby.
Kitchen
Pet-friendly
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
The price is CA $268 per night
CA $268
CA $295 total
Sep 20 - Sep 21
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
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 $188 per night
CA $188
CA $217 total
Oct 18 - Oct 19
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
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 $222 per night
CA $222
CA $241 total
Oct 18 - Oct 19
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 Barrette Center for the Arts and New England Transportation Institute and Museum 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 $978 per night
CA $978
CA $1,137 total
Sep 20 - Sep 21
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 Middle Covered Bridge and Woodstock Town Hall Theatre are located nearby.
Pool
Hot tub
Hilton Garden Inn Hanover Lebanon

Hilton Garden Inn Hanover Lebanon

3 out of 5
35 Labombard Rd Lebanon NH
Free cancellation
Reserve now, pay when you stay
The price is CA $257 per night
CA $257
CA $279 total
Sep 20 - Sep 21
includes taxes & fees
Book a stay at this business-friendly hotel in Lebanon. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions AVA Gallery and Art Center and Lebanon Opera House are located nearby.
Pool
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.

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.
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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 . 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.