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.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $575, price is now $446 per person
$446
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Springfield (VSF)
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking and luggage storage are also offered on site.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $601, price is now $491 per person
$491
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,628, price is now $1,346 per person
$1,346
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $1,191, price is now $1,022 per person
$1,022
per person
Nov 5 - Nov 10
found 17 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Springfield (VSF)
A rooftop terrace is featured at this hotel, along with free self parking. WiFi in public areas is free. A garden, a lobby fireplace, and a picnic area are also on offer.
Chalet 239

Chalet 239

2 out of 5
Price was $553, price is now $476 per person
$476
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip flight included
Chicago (ORD) 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.

Top Windsor hotels deals

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
$160 nightly
The price is $174 total per night
$174 total
Aug 24 - Aug 25
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
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $119 total per night
$119 total
Aug 24 - Aug 25
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

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$449 nightly
The price is $494 total per night
$494 total
Sep 7 - Sep 8
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
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
$156 nightly
The price is $172 total per night
$172 total
Sep 6 - Sep 7
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
Holiday Inn Express Hotel & Suites White River Junction by IHG

Holiday Inn Express Hotel & Suites White River Junction by IHG

2.5 out of 5
121 Ballardvale Dr White River Junction VT
Free Cancellation
$174 nightly
The price is $191 total per night
$191 total
Aug 30 - Aug 31
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Parking included
Super 8 by Wyndham White River Junction

Super 8 by Wyndham White River Junction

2 out of 5
442 North Hartland Rd White River Junction VT
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $94 total per night
$94 total
Sep 6 - Sep 7
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. A terrace, a picnic area, and laundry facilities are also on offer.
Breakfast included
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

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 $446. 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

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.