Windsor Vacations

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Find the Best Windsor Vacation Packages

Windsor Hotel Deals

Maine Evergreen Hotel, Ascend Hotel Collection

Maine Evergreen Hotel, Ascend Hotel Collection

2.5 out of 5
65 Whitten Rd, Augusta, ME
Fully refundableReserve now, pay when you stay
The price is ￥24,750 per night from Aug 17 to Aug 18
￥24,750
￥26,978 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
Paintings by local artists
"My sister, niece and I stayed here for one night in July. The hotel was comfortable and clean, and the front desk staff member who checked us in was very friendly. Also, we loved all the paintings by local artists that were displayed throughout the hotel."

Reviewed on Jul 21, 2025

Maine Evergreen Hotel, Ascend Hotel Collection
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 ￥20,608 per night from Jul 28 to Jul 29
￥20,608
￥22,463 total
Jul 28 - Jul 29
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"Helpful staff, great location"

Reviewed on Jul 22, 2025

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 ￥24,649 per night from Aug 24 to Aug 25
￥24,649
￥26,868 total
Aug 24 - Aug 25
includes taxes & fees
7.6/10 Good! (1,003 reviews)
"The restrooms need updating"

Reviewed on Jul 19, 2025

Senator Inn & Spa
See all 674 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'll find cheap prices 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?
You're likely to find reduced prices and greater availability in January, February and March. Browse our cheap Windsor vacation packages and you could land some great off-season deals.
How many days is enough for Windsor?
With a well-organized schedule, you can easily tick off the most popular Windsor attractions in a handful of days. But if you want 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.
How to plan a trip to Windsor?

  1. Pick the right time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to go to Windsor.
  2. Figure out your budget: Ensure you have enough money to cover everything from meals and transportation to flights and activities. Your hotel will probably be the biggest expense during your trip to Windsor.
  3. Decide your trip length: Think about how long you'd like to spend discovering Windsor. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to pick a Windsor vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.