Deals on vacations and trips to Windsor

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Windsor flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,226, price is now $1,067 per person
$1,067
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Washington (IAD) to Springfield (VSF)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $2,869, price is now $2,479 per person
$2,479
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Washington (IAD) to Springfield (VSF)
Ski-in/ski-out access, 2 restaurants, and 3 hot tubs are all featured at this smoke-free hotel. There's a free ski shuttle, and ski lessons, ski passes and ski storage are available on site. Bring the family and enjoy the mini golf, playground, and arcade/game room.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,940, price is now $1,819 per person
$1,819
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Washington (IAD) to Springfield (VSF)
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.
Lincoln Inn & Gallery

Lincoln Inn & Gallery

2 out of 5
West Woodstock
Price was $1,102, price is now $1,102 per person
$1,102
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Washington (IAD) to Springfield (VSF)
This inn doesn't skimp on freebies - guests receive free WiFi and free self parking. A fireplace in the lobby and a picnic area are also provided.

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
$113 nightly
The price is $124 total per night
$124 total
Feb 8 - Feb 9
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
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
$173 nightly
The price is $191 total per night
$191 total
Feb 1 - Feb 2
Total with taxes and fees
This hotel features a 24-hour gym and a hot tub. There's a free ski shuttle, and ski passes and ski storage are available on site. WiFi in public areas is free.
Hot Tub
Pet friendly
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
$235 nightly
The price is $259 total per night
$259 total
Jan 15 - Jan 16
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
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$161 nightly
The price is $175 total per night
$175 total
Jan 14 - Jan 15
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. 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
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$359 nightly
The price is $395 total per night
$395 total
Jan 19 - Jan 20
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
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
Free Cancellation
Reserve now, pay when you stay
$120 nightly
The price is $132 total per night
$132 total
Jan 12 - Jan 13
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
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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

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

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

Frequently asked questions

How much are vacation packages to Windsor?
Travelocity offers flight and hotel vacation packages starting as low as $1,067. 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.

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