Windsor Vacations from $385

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The Latest Windsor vacation packages

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

Hampton Inn Augusta

2.5 out of 5
Price was $430, price is now $385 per person
$385
per person
Feb 12 - Feb 15
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
9.4/10 Exceptional! (739 reviews)
Clean, comfortable, courteous staff, great breakfast. Our stay was great!

Reviewed on Jan 5, 2026

OneSixtyFive

OneSixtyFive

3 out of 5
Price was $680, price is now $581 per person
$581
per person
Feb 26 - Mar 1
found 5 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Augusta (AUG)
9.4/10 Exceptional! (142 reviews)
Clean, quiet, and comfortable. Very nice setting in the carriage house, enjoyable stay.

Reviewed on Nov 1, 2025

Pressey House Lakeside Bed & Breakfast

Pressey House Lakeside Bed & Breakfast

3 out of 5
Price was $1,408, price is now $1,210 per person
$1,210
per person
Mar 15 - Mar 19
found 23 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Augusta (AUG)
No reviews
My Valhalla Farm

My Valhalla Farm

3.5 out of 5
Price was $1,321, price is now $1,147 per person
$1,147
per person
Mar 15 - Mar 19
found 23 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Augusta (AUG)
No reviews
The Brunswick Hotel

The Brunswick Hotel

3 out of 5
Price was $623, price is now $547 per person
$547
per person
Mar 14 - Mar 17
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
9.4/10 Exceptional! (868 reviews)
Very friendly staff, clean room with comfortable bed, nice reception area with fireplace and place to do a little work.

Reviewed on Jan 3, 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
$113 nightly
The price is $124 total per night from Jan 24 to Jan 25
$124 total
Jan 24 - Jan 25
Total with taxes and fees
9.2/10 Wonderful! (1,006 reviews)
The comfort and cleanliness of the room and the staff was very accommodating. We went down and listened to the musical guest for awhile. It was fabulous!

Reviewed on Jan 4, 2026

Maine Evergreen Hotel, an Ascend Collection Hotel
Senator Inn & Spa

Senator Inn & Spa

3 out of 5
284 Western Ave Augusta ME
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $101 total per night from Jan 25 to Jan 26
$101 total
Jan 25 - Jan 26
Total with taxes and fees
7.8/10 Good! (1,002 reviews)
Pet friendly room was a bit dated, but the fact that you ould access room both from outside and inside was very convenient. Staff was thoughtful and pleasant. Parking lot plowed early following a night of snow.

Reviewed on Dec 27, 2025

Senator Inn & Spa
Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

2 out of 5
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $116 total per night from Jan 15 to Jan 16
$116 total
Jan 15 - Jan 16
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
Easy and smooth nice access to interstate. The to go breakfast was perfect

Reviewed on Jan 1, 2026

Fireside Inn & Suites Waterville
See all 650 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 $385 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.