Windsor Vacations from $385
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The Latest Windsor vacation packages
Price found within the past 48 hours. Click for updated prices.
Grand Summit Hotel
$385
per person
Dec 13 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Augusta (AUG)
8.4/10 Very Good! (416 reviews)
Wonderful experience. Clean room as well as hallways and the entire building. Staff were excellent. Professional, knowledgeable and friendly. Just a great place! Very few restaurants but there was a market to the left of the entrance that had some wonderful cooked food so we were able to eat in which was a nice little experience for us.
Reviewed on Oct 18, 2026
Jordan Hotel
$396
per person
Dec 13 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Jacksonville (JAX) to Augusta (AUG)
9/10 Wonderful! (576 reviews)
Beautiful, clean hotel with gorgeous mountain views. We stayed here for a wedding in town and it was so comfortable. We used the heated outdoor pool on a chilly night in October and it was so warm and clean. We also used the hot tub and sauna. Everything is clean and well maintained. Will definitely stay here again if we are in the area.
Reviewed on Oct 18, 2026
Windsor Hotel Deals
Maine Evergreen Hotel, an Ascend Collection Hotel
65 Whitten Rd Augusta ME
Fully refundable
$128 nightly
$140 total
Nov 15 - Nov 16
Total with taxes and fees
9.4/10 Exceptional! (1,009 reviews)
"Great flat bread and great breakfast"
Reviewed on Oct 18, 2026
Fireside Inn & Suites Waterville
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
$111 nightly
$121 total
Nov 1 - Nov 2
Total with taxes and fees
Senator Inn & Spa
284 Western Ave Augusta ME
Fully refundableReserve now, pay when you stay
$100 nightly
$109 total
Nov 10 - Nov 11
Total with taxes and fees
8/10 Very Good! (1,003 reviews)
"The staff was very pleasant and friendly. You can tell the property is older and needs some updating."
Reviewed on Oct 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
What's included in a Windsor vacation package?
A Windsor vacation package lets you combine round-trip flights, a hotel stay, and a rental car. This makes it easy to explore the area's natural beauty, with flights typically arriving at Portland International Jetport (PWM).Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
How can I save money on a Windsor vacation package?
When you bundle, you can save up to 30%*. To save money on a Windsor package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What are the top things to do in Windsor?
A Windsor vacation offers a chance to explore nature and enjoy outdoor activities:Browse and book things to do in Windsor on Expedia.
Do you need to rent a car in Windsor, or is public transport enough?
For a Windsor vacation package, renting a car is generally recommended to fully explore the area. As an outdoor and nature destination outside a city, Windsor's attractions are spread out, and a car provides the most flexibility to reach places like Damariscotta Lake or the Kennebec River. Having your own vehicle is ideal for day trips and accessing various outdoor activities. When booking Windsor vacation packages with flights, consider adding a rental car for convenient travel from airports like Portland International Jetport (PWM) or Bangor International Airport (BGR).
Can I change or cancel my Windsor vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Windsor vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Windsor vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Windsor?
To find last-minute vacation packages to Windsor, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Windsor vacation packages?
Free cancellation on a Windsor vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Windsor vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Windsor getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Windsor vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.
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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.
