Windsor Vacation Packages 2026

Top Windsor hotels deals

Fat Sheep Farm & Cabins

122 Best Rd Windsor VT

$182 nightly

$198 total

Nov 1 - Nov 2

Total with taxes and fees

This cabin doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. A terrace, a garden, and a picnic area are also on offer.

Kitchen

Pet friendly

Fireside Inn & Suites West Lebanon

25 Airport Road West Lebanon NH

Free Cancellation

Reserve now, pay when you stay

$128 nightly

$139 total

Nov 9 - Nov 10

Total with taxes and fees

This hotel features an indoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Pool

Hot Tub

The Mountain Inn at Killington

47 Old Mill Rd Killington VT

Free Cancellation

Reserve now, pay when you stay

$156 nightly

$172 total

Oct 19 - Oct 20

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the free ski shuttle and onsite ski storage. Enjoy the gym and free perks like continental breakfast and free self parking.

Pool

Breakfast included

White River Inn and Suites

91 Ballardvale Drive White River Junction VT

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$108 total

Nov 1 - Nov 2

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's an indoor pool on site, and a 24-hour front desk and a terrace are also provided.

Pool

Breakfast included

Align Inn Vermont

5817 Woodstock Rd Quechee VT

$115 nightly

$126 total

Nov 1 - Nov 2

Total with taxes and fees

This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

Woodstock Inn & Resort

Fourteen The Green Woodstock VT

$459 nightly

$505 total

Nov 10 - Nov 11

Total with taxes and fees

This luxury resort features a golf course, a full-service spa, and 4 restaurants. Enjoy the 2 indoor tennis courts and perks like free valet parking and free WiFi. Relax with a drink at one of the 2 bars/lounges and enjoy the 2 hot tubs and indoor pool.

Pool

Hot Tub

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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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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 100 mi 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 60 mi from the city center and is the starting point for many unforgettable experiences. Alternatively, Lebanon Municipal Airport (LEB) is 11 mi away from central Windsor and Rutland Southern Vermont Regional Airport (RUT) is 30 mi 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.