Windsor Vacations from $760
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The Latest Windsor vacation packages
Price found within the past 48 hours. Click for updated prices.
Topside Inn
$1,513
per person
Oct 1 - Oct 6
found 19 hours ago
Roundtrip flight included
Chicago (CHI) to Augusta (AUG)
10/10 Exceptional! (137 reviews)
It was great all around. The room was great. The food was great and the view from our room beautiful. Easy walk to the shops and the pier. I would highly recommend a stay.
Reviewed on Aug 19, 2026
Mid-Town Motel
$1,319
per person
Oct 9 - Oct 15
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Augusta (AUG)
8.6/10 Excellent! (254 reviews)
We were looking for a quaint little motel and Mid Town Motel was perfect. We were able to grab the last room which only had twin beds, but we didn’t mind for our short stay. The beds and pillows were extremely comfortable. The employees were both helpful and friendly. We will definitely return.
Reviewed on Aug 17, 2026
Linekin Bay Resort
$964
per person
Oct 5 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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
$157 total
Aug 31 - Sep 1
Total with taxes and fees
9.2/10 Wonderful! (1,004 reviews)
"Everything about this hotel is excellent including breakfast"
Reviewed on Aug 18, 2026
Fireside Inn & Suites Waterville
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
$112 nightly
$122 total
Sep 9 - Sep 10
Total with taxes and fees
Senator Inn & Spa
284 Western Ave Augusta ME
Fully refundableReserve now, pay when you stay
$127 nightly
$139 total
Aug 30 - Aug 31
Total with taxes and fees
8/10 Very Good! (1,020 reviews)
"Has the inventor of the wellness wedge?I travel cross-country often.This hotel was a nice surprise. The head of the bed in every room was approximately 3 inches lower than the foot of the bed.However , I had my wellness which wedges with me. Great place to stay great staff.Nice breakfast"
Reviewed on Aug 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 $760 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.
