Windsor Vacations from $606
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The Latest Windsor vacation packages
Price found within the past 48 hours. Click for updated prices.
Stone Park
$830
per person
Nov 3 - Nov 7
found 5 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Augusta (AUG)
9.4/10 Exceptional! (332 reviews)
Our room was huge, but we would have preferred a king bed. The bed was listed as a queen but felt more like just a full size bed. Very nice, clean room! Close to Trenton and the Acadia Gateway Center which was great!
Reviewed on Sep 18, 2026
Windsor Hotel Deals
Maine Evergreen Hotel, an Ascend Collection Hotel
65 Whitten Rd Augusta ME
Fully refundable
$145 nightly
$158 total
Oct 18 - Oct 19
Total with taxes and fees
9.4/10 Exceptional! (1,002 reviews)
"Great spot,easy access off the highway,nice pub & eatery,great supper & breakfast,lots of hot water too,would return anytime"
Reviewed on Sep 18, 2026
Fireside Inn & Suites Waterville
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
$117 nightly
$128 total
Oct 4 - Oct 5
Total with taxes and fees
Senator Inn & Spa
284 Western Ave Augusta ME
Fully refundableReserve now, pay when you stay
$128 nightly
$140 total
Oct 19 - Oct 20
Total with taxes and fees
8/10 Very Good! (1,007 reviews)
"Stayed in a suite and loved it. Huge rooms. Three TV's. Extra vanity. TV/workroom. Liked this place."
Reviewed on Sep 18, 2026
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.
Find the Best Windsor Vacation Packages
Windsor Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Knox County Regional Airport (RKD) |
Population | 2,300 |
Top Sights | Maine State Museum, Johnson Hall and Capitol Park |
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Frequently asked questions
How much does a Windsor vacation package cost?
You'll find cheap prices from $606 on Expedia for your Windsor break. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Windsor costs.
What are the cheapest months to go to Windsor?
If you're hoping to snag a cheap Windsor vacation package, consider planning a trip in October, November and December. You'll generally find better prices on accommodations and flights during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Windsor?
With a well-planned itinerary, you can easily tick off the most popular Windsor attractions in a handful of days. But if you'd like to discover hidden spots or take day trips, think about booking your Windsor vacation for longer.
How to find the best Windsor package deals?
Use Expedia's filters to find some unbeatable Windsor package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Windsor package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Windsor vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still have the freedom to create a customized Windsor vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Windsor?
Enjoy amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Windsor break.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
Your Windsor trip should be an escape from your daily routine, not a source of money-related stress. So to allow you a little more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
