Windsor Vacations

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Find the Best Windsor Vacation Packages

Windsor Hotel Deals

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

2.5 out of 5
65 Whitten Rd Augusta ME
Fully refundable
The price is AEDĀ 597 per night from Aug 16 to Aug 17
AEDĀ 597
AEDĀ 650 total
16 Aug - 17 Aug
includes taxes & fees
9.2/10 Wonderful! (1,018 reviews)
"The rooms were clean and comfortable. Breakfast was decent. Vanilla yogurt and the granola was especially tasty along with warm muffins. My only complaint is that I was given the impression this was a hotel but the standard rooms are basically a motel. I donā€™t think itā€™s worth a nicer hotel price ..."

Reviewed on 16 July 2026

Maine Evergreen Hotel, an Ascend Collection Hotel
Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

2 out of 5
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
The price is AEDĀ 469 per night from Aug 16 to Aug 17
AEDĀ 469
AEDĀ 511 total
16 Aug - 17 Aug
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Staff were very friendly. Room was clean enough, though dated and somewhat cramped. We were placed on the second floor, but there was no elevator. And the free breakfast was a grab 'n go style, rather than a sit down or hot breakfast. So it was a bit overpriced imo, but I can't say it was bad. It ..."

Reviewed on 16 July 2026

Fireside Inn & Suites Waterville
Senator Inn & Spa

Senator Inn & Spa

3 out of 5
284 Western Ave Augusta ME
Fully refundableReserve now, pay when you stay
The price is AEDĀ 518 per night from Aug 2 to Aug 3
AEDĀ 518
AEDĀ 565 total
2 Aug - 3 Aug
includes taxes & fees
Senator Inn & Spa
See all 725 properties in Windsor
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.

Frequently asked questions

How much does a Windsor vacation package cost?
You can snap up a vacation package to this top destination on Expedia. However, how much your vacation to Windsor costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Windsor?
If you'd like to book a cheap Windsor vacation package, consider planning a trip in January, February and March. You'll usually find better prices on hotels and flights during these months ā€” perfect for budget-conscious travelers.
How to find the best Windsor package deals?
Use Expedia's filters to find some great Windsor package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Windsor package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Windsor vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still have the freedom to create a personalized Windsor vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Windsor?
If you're planning a spur-of-the-moment Windsor adventure, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Windsor?

  1. Choose your dates: What you'd like to do in Windsor and your preferred season will help you decide when to travel.
  2. Plan your budget wisely: Besides the price of your stay, you should factor in other expenses. These include food, flights and transportation. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Windsor.
  3. Decide how many days away: Start by compiling a list of the activities and attractions you want to experience in Windsor. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to choose a Windsor vacation package that brings all your bookings together.