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Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.
Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.
182 customers have saved 100% on their flight when booking a Flight + Hotel together this year!
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182 customers have saved 100% on their flight when booking a Flight + Hotel together this year!

2021 Windsor vacation packages

Cheap Hotels for your vacation in Windsor

Windsor Mansion Inn

Windsor Mansion Inn

153 Pembroke Road, Windsor, VT
    3.5 out of 5.0

    Situated in a regional park, this bed & breakfast is within 3 mi (5 km) of American Precision Museum, Cornish-Windsor Covered Bridge, and Harpoon Brewery. Saint-Gaudens ...


    Fat Sheep Farm & Cabins

    Fat Sheep Farm & Cabins

    122 Best Rd, Windsor, VT
      3.0 out of 5.0

      Situated in Windsor, this farm stay is within 9 mi (15 km) of Mt Ascutney State Park, Mt Ascutney Hospital and Health Center: Primary Care - Windsor, and Path ...


      Windsor Vacation Deal FAQ's

      Where to find Windsor package deals?

      On CheapTickets, you can find package deals in Windsor as low as $413!

      When is peak season in Windsor?

      are very popular times to visit Windsor.

      When is the best time to visit Windsor?

      If you're looking for cheap vacations to Windsor, is the best time to visit Windsor.

      When is the worst time time to visit Windsor?

      Prices for Windsor vacations can peak during .

      When is low season in Windsor?

      We have found to be the least-crowded time of the year to visit Windsor.

      Your Windsor Vacation Guide

      Where is Windsor?

      Hey there, fellow penny-pinchers. We know you want to make the most out of your Windsor escape for the least amount of green stuff. But first, let's brush up on this unique destination!

      It can be found 10 miles to the north-west of Claremont, and 398 miles north-east of Washington, the national capital.

      This area of Central Vermont- Killington is home to approximately 2,100 residents.

      Cheap Things to do in Windsor

      It's a satisfying sensation when you get back to your hotel room after a massive day of sightseeing and discover your wallet's still full of cash! If you'd love to experience this feeling during your break, read through our list of free things to do and see in or near Windsor:

      • Discover a little about the local history without having to stump up for pricy admittance fees at Old Constitution House, Cornish-Windsor Covered Bridge and Blow-Me-Down Bridge. These free attractions offer an intriguing glimpse into the region's distinct culture.
      • Find out if you can take a tour of South Congregational Church. Otherwise, it's still worth appreciating from outside — there's always something uplifting about visiting spiritual structures.
      • Mt Ascutney State Park is one of the area's most beautiful natural landmarks. Drop by to marvel at the views and get a little fresh air!
      • Have a break from the urban jungle and admire the beauty of nature at Billings Park and Trail. This attractive place is perfect for those yearning a bit of downtime.

      Cheap Windsor Vacation Package Deals

      Don't let the fear of having to settle for a small, sad room stop you from going on that adventure. When you arrange your travels with CheapTickets, you won't have to part with too many of your pennies or give up quality.

      To travel cheap is to travel without all sorts of options, right? Wrong! With 500 airlines and over 500,000 properties all over the world, you're loaded with choice. And the best part is you'll save as much as $290^ if you combine your bookings on hotels and flights.

      The less money you spend the better you feel, and with our Price Guarantee you'll be feeling like a million bucks. Here's what you need to know — we'll reimburse the difference if you find your vacation package for a lower rate within 48 hours of booking.

      Get CheapCash

      Just like you, we're passionate about cheap. That's one of the reasons we implemented our simple rewards program. All you've got to do is book flights and we'll treat you to fabulous savings on qualifying CheapTickets hotels.

      Wondering what to do to access savings, exclusive bonus offers and extra-thrifty perks? Simply log in to your account or sign up for a new one for free and then join CheapCash. It's that simple!

      Cheap Car Rentals in Windsor

      We understand — you've already spent your precious dosh on your getaway, so you have no interest in coughing up for taxis. Luckily for you, Windsor has some good car rental places which will make things easier on your vacation budget.

      Cheap Hotels in Windsor

      We'll make arranging your trip as straightforward as possible. Recommended hotels include the Holiday Inn Club Vacations Mount Ascutney Resort and the Snapdragon Inn.

      ^Savings based on all package bookings made with Flight + Hotel on from January 1, 2019 to December 31, 2019, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. 

      *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.