Windsor Vacation Packages

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Top Windsor Vacation Deals

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

Topside Inn

3 out of 5
Price was CA $1,650, price is now CA $1,284 per person
CA $1,284
per person
Aug 31 - Sep 3
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Augusta (AUG)
10/10 Exceptional! (113 reviews)
First, the location. What a beautiful view. Next, the room was so nicely renovated. The modern amenities with old world charm. The bathroom was so liluxorious. Next the breakfast was superb. And the extra touches like unlimited drinks and water, freshly baked cookies. Definitely coming back next year.

Reviewed on Jul 12, 2026

Stone Park

Stone Park

4 out of 5
Price was CA $2,119, price is now CA $1,532 per person
CA $1,532
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Augusta (AUG)
9.2/10 Wonderful! (234 reviews)
Everything was updated, clean & as seen on the website.

Reviewed on Jul 12, 2026

House near Acadia National Park

House near Acadia National Park

4 out of 5
Price was CA $4,619, price is now CA $3,457 per person
CA $3,457
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Augusta (AUG)
9.6/10 Exceptional! (25 reviews)
Nice clean place, but one of the rooms was not how it was pictured. Instead of a queen, it had bunk beds. Water pressure was great upstairs but low downstairs in the bathroom. Also, ice maker didn't work. Great location

Reviewed on Jun 25, 2026

Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

3 out of 5
Price was CA $2,600, price is now CA $1,958 per person
CA $1,958
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Augusta (AUG)
8.2/10 Very good! (1,000 reviews)
I wrote on the required paper for towels and never received it.

Reviewed on Jul 12, 2026

Newly Renovated Acadia Apartment Maple Street

Newly Renovated Acadia Apartment Maple Street

3 out of 5
Price was CA $2,931, price is now CA $2,255 per person
CA $2,255
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Augusta (AUG)
10/10 Exceptional! (3 reviews)
Entry door was confusing.

Reviewed on Jul 1, 2026

Ready to book your vacation to Windsor?

 

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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 CA $254 per night from Jul 27 to Jul 28
CA $254
CA $276 total
Jul 27 - Jul 28
includes taxes & fees
9.2/10 Wonderful! (1,013 reviews)
"Older hotel. Our room had a big patch on the ceiling and a very slow toilet. Small beds. Breakfast was only ok, nothing better than others we have used. Staff were friendly, but overall underwhelmed by the property"

Reviewed on Jul 11, 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 CA $182 per night from Aug 2 to Aug 3
CA $182
CA $198 total
Aug 2 - Aug 3
includes taxes & fees
8.8/10 Excellent! (1,020 reviews)
"Our expectations were not terribly high when we made the reservations--just a place to stay overnight, near where we were going to be the next day. It is located just off I-95, and is located at the beginning of a shopping center, so we figured it was just another place. When we arrived, it looked ..."

Reviewed on Jul 12, 2026

Fireside Inn & Suites Waterville
Best Western Plus Augusta Civic Center Inn

Best Western Plus Augusta Civic Center Inn

2.5 out of 5
110 Community Drive Augusta ME
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Aug 2 to Aug 3
CA $164
CA $179 total
Aug 2 - Aug 3
includes taxes & fees
7.8/10 Good! (1,009 reviews)
"Parking lot was a little shady around the side. Homeless men near my vehicle on the side of the building wished I realized it before parking near that side of the building"

Reviewed on Jul 10, 2026

Best Western Plus Augusta Civic Center Inn
See all 726 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations

Frequently asked questions

How much does a Windsor vacation package cost?
You can snap up a vacation package to this top destination from CA $1,284 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.

Explore a world of travel with Expedia

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