Windsor Vacations from $481

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The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Grand Summit Hotel

Grand Summit Hotel

3 out of 5
Price was $600, price is now $481 per person
$481
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Augusta (AUG)
8.4/10 Very Good! (381 reviews)
Lovely hotel, comfortable and clean. Loved the outdoor amenities.

Reviewed on Jul 11, 2026

Spruce Point Inn

Spruce Point Inn

3.5 out of 5
Price was $1,373, price is now $1,038 per person
$1,038
per person
Oct 2 - Oct 6
found 20 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Augusta (AUG)
8.8/10 Excellent! (411 reviews)
A wonderful family retreat. Felt like stepping back in time in the best way. We look forward to returning!

Reviewed on Jul 11, 2026

Topside Inn

Topside Inn

3 out of 5
Save 100% on your flight
Price was $852, price is now $645 per person
$645
per person
Sep 11 - Sep 13
found 14 hours ago
Roundtrip flight included
Washington (WAS) 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

House near Acadia National Park

House near Acadia National Park

4 out of 5
Price was $1,793, price is now $1,430 per person
$1,430
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 $1,067, price is now $864 per person
$864
per person
Sep 11 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Augusta (AUG)
8.2/10 Very Good! (1,000 reviews)
The front desk staff were very friendly and helpful. They helped me navigate how to reserve my trip to Cadillac Mountain at Acadia National Park. The room was clean and spacious. I would stay here again if ever in town.

Reviewed on Jul 10, 2026

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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
$166 nightly
The price is $181 total per night from Aug 2 to Aug 3
$181 total
Aug 2 - Aug 3
Total with taxes and 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
$129 nightly
The price is $140 total per night from Aug 2 to Aug 3
$140 total
Aug 2 - Aug 3
Total with taxes and 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
$116 nightly
The price is $126 total per night from Aug 2 to Aug 3
$126 total
Aug 2 - Aug 3
Total with taxes and 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 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.

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

How much does a Windsor vacation package cost?
You'll find cheap prices from $481 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?
If you're hoping to snag a cheap Windsor vacation package, consider planning a trip in October, November and December. You'll generally find better prices on accommodations and flights during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Windsor?
With a well-planned itinerary, you can easily tick off the most popular Windsor attractions in a handful of days. But if you'd like 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.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
Your Windsor trip should be an escape from your daily routine, not a source of money-related stress. So to allow you a little more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.

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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.