Windsor Vacations from $582
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The Latest Windsor vacation packages
Price found within the past 48 hours. Click for updated prices.
Comfort Inn Ellsworth - Bar Harbor
$582
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Augusta (AUG)
9.2/10 Wonderful! (1,008 reviews)
Breakfast selections were very good the food was prepared very nicely. The location of the hotel is excellent
Reviewed on Aug 14, 2026
Jordan Hotel
$767
per person
Sep 22 - Sep 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Augusta (AUG)
8.8/10 Excellent! (549 reviews)
We came in late and left early so we didn’t see much or explore the property. It was ok. It felt a bit dated but the room was clean and staff was very friendly.
Reviewed on Aug 10, 2026
Linekin Bay Resort
$1,111
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
9.2/10 Wonderful! (231 reviews)
The views from the property and our room were amazing. Our trip was so relaxing that we did not want to leave. The staff was extremely friendly and helpful. There were plenty of activities for both adults and children. The complimentary boat ride and trolley were unexpected and a great addition to our trip. We are already planning our next trip for 2027.
Reviewed on Aug 14, 2026
Windsor Hotel Deals
Maine Evergreen Hotel, an Ascend Collection Hotel
65 Whitten Rd Augusta ME
Fully refundable
$143 nightly
$156 total
Aug 30 - Aug 31
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
"Wonderful one night stay"
Reviewed on Aug 14, 2026
Senator Inn & Spa
284 Western Ave Augusta ME
Fully refundableReserve now, pay when you stay
$130 nightly
$142 total
Aug 31 - Sep 1
Total with taxes and fees
Fireside Inn & Suites Waterville
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
$112 nightly
$122 total
Aug 23 - Aug 24
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
"Room was clean. We got a renovated room which was nice."
Reviewed on Aug 13, 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 $582 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.
Explore a world of travel with Expedia
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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.
