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.
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
per person
Aug 26 - Aug 31
found 16 hours ago
Roundtrip non-stop flight included
Bloomington (BMI) to Springfield (VSF)
This smoke-free resort features ski-in/ski-out access, a full-service spa, and a restaurant. Enjoy the outdoor pool and perks like free valet parking and a free area shuttle. You'll appreciate the gym, bar/lounge, and laundry facilities.
Farm Road Estate

Farm Road Estate

3 out of 5
per person
Aug 26 - Aug 31
found 16 hours ago
Roundtrip non-stop flight included
Bloomington (BMI) to Springfield (VSF)
This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, and a lobby fireplace are also on offer.
Chalet 239

Chalet 239

2 out of 5
per person
Aug 26 - Aug 31
found 16 hours ago
Roundtrip non-stop flight included
Bloomington (BMI) to Springfield (VSF)
The motel doesn't skimp on freebies - guests receive free on-the-go breakfast and free self parking. A picnic area and a virtual front desk are also provided.
Mount Snow Lodging

Mount Snow Lodging

3 out of 5
per person
Aug 26 - Aug 31
found 16 hours ago
Roundtrip non-stop flight included
Bloomington (BMI) to Springfield (VSF)
Inn At Mount Snow

Inn At Mount Snow

2 out of 5
per person
Aug 26 - Aug 31
found 16 hours ago
Roundtrip non-stop flight included
Bloomington (BMI) to Springfield (VSF)
This hotel features free WiFi in public areas, a virtual front desk, and free self parking. Enjoy the free ski shuttle and onsite ski storage. Enjoy the free continental breakfast each morning.

Top Windsor hotels deals

Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd, Quechee, VT
Free Cancellation
Reserve now, pay when you stay
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This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
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
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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
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
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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
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Free Cancellation
Reserve now, pay when you stay
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This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
Pet friendly
Parking included
Hanover Inn Dartmouth

Hanover Inn Dartmouth

4 out of 5
Two East Wheelock Street, Hanover, NH
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A terrace, a lobby fireplace, and a computer station are also on offer.
Pet friendly
Free WiFi
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
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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
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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

4.5/5(5 reviews)

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 $640. 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