Deals on vacations and trips to Windsor

Save when you book Windsor, MA package deals

Choose two or more items and save on your trip:

Windsor flight + hotel vacation packages

Fairfield Inn & Suites by Marriott Albany Downtown
Hampton Inn & Suites Albany-Downtown
Hotel Luna
Red Roof Inn Clifton Park
Motel 6 Albany, NY
Prices and availability subject to change. Additional terms may apply.

Top Windsor hotels deals

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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.

Frequently asked questions

How much are vacation packages to Windsor?
Exciting adventures await in Windsor, with Travelocity vacation packages from as low as $464. Offering both hotels and flights, these awesome deals make it super simple to discover every corner of the world.
Where can I get the best vacation package deals for Windsor?
It’s hard to beat Travelocity when it comes to finding your Windsor package deal. There are as many as 400 air carriers and 1,000,000 properties worldwide to select from. Book your vacation now and get ready to cross another destination off your to-do list.
Why should I purchase my Windsor vacation package with Travelocity?
Because we believe in creating special vacation experiences. From hotels and flights to car rentals and activities, everything is at your fingertips. Our customer support team is available 24/7 to make sure you’re never alone. We also have an amazing Price Match Guarantee, so you can secure your vacation knowing you’ve landed the best deal possible. Find a lower price and we’ll match it!
Can I save on my Windsor car rental if I combine it with a hotel or flight?
Combining your flight, hotel and car into a Windsor vacation package is the best way to score better prices. Plus, having your own rental car gives you absolute freedom to make your way to all the landmarks you’re hoping to explore. Sitting 100 mi away from Windsor, Fenway Park is one place that should be on your can’t-miss list. Fasten your seat belt and make a day trip of it.
What is the best time of year to go to Windsor?
If you’re watching your pennies, is a terrific month to explore this part of the world, whereas is the costliest time of the year. February, March and May is the peak season. If you’d rather avoid big crowds, October, November and December are usually quieter.
Which airport is best for Windsor?
Bradley Intl. Airport (BDL) is popular. You’ll find it roughly 45 mi southeast of Windsor. Your other options are Albany Intl. Airport (ALB) (40 mi away from central Windsor) and Hartford, CT (HFD-Hartford - Brainard) (55 mi away from central Windsor).
Where should I stay when visiting Windsor?
The Massachusetts Vacation Rental w/ Deck & Grill is the top choice of many travelers. Book now before it’s too late.