Windsor Vacations from $284

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The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

3 out of 5
Price was $344, price is now $284 per person
$284
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Nashville (BNA) to Augusta (AUG)
8.2/10 Very Good! (1,006 reviews)
All was good. Room clean. Staff friendly and helpful.

Reviewed on Oct 7, 2025

Admirals Quarters Inn

Admirals Quarters Inn

2 out of 5
Price was $960, price is now $782 per person
$782
per person
Nov 14 - Nov 17
found 19 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Augusta (AUG)
9.4/10 Exceptional! (26 reviews)
Admiral Quarters, and the Greenleaf are both very conveniently located. Although they are Inns that were built many years ago they are tastefully, renovated, and cozy. The Inn keeper, Jersey, goes above and beyond to make his guests feel comfortable. His hospitality was a highlight of our stay. He shared his knowledge of the area, places to eat, and things to do. He took us on a boat ride of the harbor area and had a fire pit with marshmallows and s’mores when weather permitted. We will be back.

Reviewed on Sep 9, 2025

Red Cedar Haven in Sidney

Red Cedar Haven in Sidney

2 out of 5
Save 100% on your flight
Price was $3,101, price is now $2,568 per person
$2,568
per person
Nov 15 - Nov 22
found 12 hours ago
Roundtrip flight included
Nashville (BNA) to Augusta (AUG)
No reviews
Little Landing Cottage-gorgeous View BBQ Wi-fi

Little Landing Cottage-gorgeous View BBQ Wi-fi

3.5 out of 5
Save 100% on your flight
Price was $2,614, price is now $2,177 per person
$2,177
per person
Nov 15 - Nov 22
found 12 hours ago
Roundtrip flight included
Nashville (BNA) to Augusta (AUG)
10/10 Exceptional! (1 review)
I love this little cottage. I will definitely be staying again. Thank you.!!!!!

Reviewed on May 26, 2025

Sunset Chalet-amazing Views Private hot tub

Sunset Chalet-amazing Views Private hot tub

3 out of 5
Price was $2,005, price is now $1,703 per person
$1,703
per person
Nov 15 - Nov 22
found 12 hours ago
Roundtrip flight included
Nashville (BNA) to Augusta (AUG)
10/10 Exceptional! (2 reviews)
Easy to find, amenties were great for kitchen, bathroom, and game room. We look forward to going again but try one of the treehouses.

Reviewed on Nov 3, 2024

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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 refundableReserve now, pay when you stay
$139 nightly
The price is $151 total per night from Nov 2 to Nov 3
$151 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (1,008 reviews)
"Nice stay nice people !"

Reviewed on Oct 4, 2025

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
$112 nightly
The price is $122 total per night from Oct 31 to Nov 1
$122 total
Oct 31 - Nov 1
Total with taxes and fees
8.6/10 Excellent! (999 reviews)
"An older resort catering to skiers but a nice moption for hikers and leaf peepers"

Reviewed on Sep 29, 2025

Fireside Inn & Suites Waterville
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
$107 nightly
The price is $117 total per night from Nov 2 to Nov 3
$117 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (818 reviews)
"Overall nice"

Reviewed on Oct 1, 2025

Holiday Inn Express & Suites Waterville - North by IHG
See all 648 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.

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 $284 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.

Explore a world of travel with Expedia

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.