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 $800, price is now $608 per person
$608
per person
Dec 30 - Jan 4
found 14 hours ago
Roundtrip non-stop flight included
Jacksonville (JAX) 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.
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $1,229, price is now $895 per person
$895
per person
Dec 30 - Jan 4
found 14 hours ago
Roundtrip non-stop flight included
Jacksonville (JAX) 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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,297, price is now $1,000 per person
$1,000
per person
Dec 30 - Jan 4
found 14 hours ago
Roundtrip non-stop flight included
Jacksonville (JAX) 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.
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was $994, price is now $818 per person
$818
per person
Dec 30 - Jan 4
found 14 hours ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Springfield (VSF)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free buffet breakfast each morning. A garden is also provided.
Deerfield Valley Inn

Deerfield Valley Inn

2 out of 5
Price was $841, price is now $715 per person
$715
per person
Dec 30 - Jan 4
found 14 hours ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Springfield (VSF)
This bed & breakfast features free WiFi in public areas, barbecue grills, and free self parking. A free bus station shuttle is offered as well. A 24-hour business center, a garden, and a lobby fireplace are also on offer.

Top Windsor hotels deals

Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins

3 out of 5
122 Best Rd Windsor VT
$182 nightly
The price is $198 total per night
$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.
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
$128 nightly
The price is $139 total per night
$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.
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
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

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
$98 nightly
The price is $108 total per night
$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.
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
$115 nightly
The price is $126 total per night
$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.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$459 nightly
The price is $505 total per night
$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.
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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 $608. 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.