Windsor Vacations from $474

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The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Smuggler's Cove Inn

Smuggler's Cove Inn

$474
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Augusta (AUG)
9/10 Wonderful! (527 reviews)
Breakfast was awesome! Views were wonderful. Very relaxing!!

Reviewed on Sep 19, 2026

The Brunswick Hotel

The Brunswick Hotel

$1,008
per person
Oct 22 - Oct 26
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Augusta (AUG)
9.4/10 Exceptional! (1,006 reviews)
Excellent location. Right across street from the train station. Easy walk to downtown restaurants and quaint shops. Gorgeous outdoor space with fire pit. Several places to sit and relax or play games in the lobby or on the covered porch. Staff was extremely friendly and available. Rooms were immaculate and had all amenities needed.

Reviewed on Sep 17, 2026

Topside Inn

Topside Inn

$747
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Augusta (AUG)
10/10 Exceptional! (154 reviews)
Perfect stay. Clean. Beautiful view

Reviewed on Sep 19, 2026

Stone Park

Stone Park

$616
per person
Nov 4 - Nov 7
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
9.4/10 Exceptional! (332 reviews)
Great place to stay! Very clean! Bed is comfortable. Coffee cakes for breakfast were yummy. Close to Bar Harbor. The only thing: when you book, let them know if you have any limitations that may affect your ability to use stairs to get to the second or third floor. They do not have an elevator. Other than that we were super pleased with our stay and most definitely come back!

Reviewed on Sep 20, 2026

Senator Inn & Spa

Senator Inn & Spa

$481
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Nashville (BNA) to Augusta (AUG)
8/10 Very Good! (1,004 reviews)
Clean room, excellent staff. Restaurant and fitness equipment were a nice surprise.

Reviewed on Sep 19, 2026

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Windsor Hotel Deals

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

65 Whitten Rd Augusta ME
Fully refundable
$148 nightly
$161 total
Oct 18 - Oct 19
Total with taxes and fees
9.4/10 Exceptional! (1,002 reviews)
"Great spot,easy access off the highway,nice pub & eatery,great supper & breakfast,lots of hot water too,would return anytime"

Reviewed on Sep 18, 2026

Maine Evergreen Hotel, an Ascend Collection Hotel
Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
$117 nightly
$128 total
Oct 4 - Oct 5
Total with taxes and fees
Fireside Inn & Suites Waterville
Senator Inn & Spa

Senator Inn & Spa

284 Western Ave Augusta ME
Fully refundableReserve now, pay when you stay
$128 nightly
$140 total
Oct 19 - Oct 20
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
"Clean room, excellent staff. Restaurant and fitness equipment were a nice surprise."

Reviewed on Sep 19, 2026

Senator Inn & Spa
See all 714 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 $474 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.