Windsor Vacation Packages

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Top Windsor Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Bingham Motor Inn

Bingham Motor Inn

2 out of 5
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Augusta (AUG)
7.8/10 Good! (17 reviews)
Clean and easy check in

Reviewed on Aug. 6, 2025

Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

3 out of 5
per person
Sep 27 - Oct 4
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Augusta (AUG)
8.2/10 Very Good! (1,006 reviews)
This is a great place to stay - affordable and clean and so close to Acadia and Bar Harbor! The staff is amazing and very helpful. And it's so affordable! Would stay here again!!!

Reviewed on Aug. 4, 2025

Flagship Inn and Suites

Flagship Inn and Suites

2.5 out of 5
per person
Sep 27 - Oct 4
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Augusta (AUG)
8.2/10 Very Good! (1,023 reviews)
A very pleasant facility, clean and convenient to Boothbay harbor. The room and the bathroom were perfectly adequate and the staff were friendly and professional.

Reviewed on Aug. 5, 2025

Spruce Point Inn

Spruce Point Inn

3.5 out of 5
per person
Sep 27 - Oct 4
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Augusta (AUG)
8.8/10 Excellent! (363 reviews)
We enjoyed our stay at Spruce Point. The amenities were great, the food was delicious, staff were kind and courteous.Housekeeping was awesome, we received service daily which some hotels do not do anymore.

Reviewed on Aug. 1, 2025

The Lodge at Pleasant Point

The Lodge at Pleasant Point

2 out of 5
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Augusta (AUG)
No reviews

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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 CA $236 per night from Aug 24 to Aug 25
CA $236
CA $257 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"great staff, and facilities were awesome! rooms are quite small but we were only there for one night, so totally doable!"

Reviewed on Aug. 3, 2025

Maine Evergreen Hotel, Ascend Hotel Collection
Holiday Inn Express & Suites Waterville - North by IHG

Holiday Inn Express & Suites Waterville - North by IHG

2.5 out of 5
332 Main St, Waterville, ME
Fully refundable
The price is CA $202 per night from Sep 4 to Sep 5
CA $202
CA $221 total
Sep 4 - Sep 5
includes taxes & fees
8.6/10 Excellent! (778 reviews)
"The beds were extremely comfortable. The facility is clean , and the staff is very friendly."

Reviewed on Aug. 3, 2025

Holiday Inn Express & Suites Waterville - North by IHG
The Elmwood

The Elmwood

2.5 out of 5
455 Kennedy Memorial Dr, Waterville, ME
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from Aug 7 to Aug 8
CA $205
CA $224 total
Aug 7 - Aug 8
includes taxes & fees
8.4/10 Very Good! (437 reviews)
"Great front desk staff. Very clean and updated rooms."

Reviewed on Aug. 1, 2025

The Elmwood
See all 666 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.
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Frequently asked questions

How much does a Windsor vacation package cost?
You can snap up a vacation package to this top destination from CA $608 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 — perfect for budget-conscious travellers.
How many days is enough for Windsor?
With a well-organized itinerary, you can easily visit the top Windsor sights in a few days. But if you'd like to discover hidden gems or go on day tours, consider booking your Windsor vacation for longer.
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 favourite 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.

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