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 Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $597, price is now $492 per person
$492
per person
Apr 29 - May 1
found 22 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Springfield (VSF)
Free WiFi in public areas is available at this hotel. Take advantage of the free self parking.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $686, price is now $588 per person
$588
per person
May 21 - May 24
just found
Roundtrip flight included
Baltimore (BWI) 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 $977, price is now $849 per person
$849
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Chicago (CHI) 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.
Mountain Lodge at Okemo

Mountain Lodge at Okemo

3 out of 5
Clock Tower Base Area
Price was $624, price is now $554 per person
$554
per person
May 21 - May 24
just found
Roundtrip flight included
Baltimore (BWI) to Springfield (VSF)
A restaurant and a gym are featured at this hotel. Take advantage of ski passes and ski storage on site, and enjoy downhill skiing and sledding. Families will appreciate the onsite laundry facilities and babysitting.

Top Windsor hotels deals

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
$156 nightly
The price is $172 total per night
$172 total
Mar 26 - Mar 27
Total with taxes and fees
This hotel features a 24-hour gym and a hot tub. Traveling on business? Take advantage of the 2 conference rooms, along with free WiFi in public areas. Self parking, a terrace, and a lobby fireplace are also offered.
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
Mar 1 - Mar 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.
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
$139 nightly
The price is $151 total per night
$151 total
Mar 16 - Mar 17
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.
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$146 nightly
The price is $159 total per night
$159 total
Mar 1 - Mar 2
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.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$349 nightly
The price is $384 total per night
$384 total
Mar 22 - Mar 23
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.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr Killington VT
Free Cancellation
Reserve now, pay when you stay
$160 nightly
The price is $176 total per night
$176 total
Mar 1 - Mar 2
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Families will appreciate the arcade/game room and onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.
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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

Bowers Covered Bridge - Vermont

Brownsville Trail

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.

Brownsville Trail
La rivière Otter Creek pour aller à Vergennes, Vermont.

Paradise Park

Explore the great outdoors at Paradise Park, a lovely green space in Windsor. Wander the riverfront in this quaint area.

Paradise Park

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 $492. 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

Cornish-Windsor Covered Bridge
Cornish-Windsor Covered Bridge
Cornish Windsor Covered Bridge
Cornish Windsor Covered Bridge
Great views of Vermont and New Hampshire.