Windsor Vacations from $533

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The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Auburn Lewiston Riverwatch

Hilton Garden Inn Auburn Lewiston Riverwatch

3 out of 5
Price was $674, price is now $533 per person
$533
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Augusta (AUG)
8.8/10 Excellent! (1,006 reviews)
We stayed here while attending a lacrosse game at Bates. The hotel staff were kind,

Reviewed on May 15, 2026

Topside Inn

Topside Inn

3 out of 5
Save 100% on your flight
Price was $1,734, price is now $1,385 per person
$1,385
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
10/10 Exceptional! (93 reviews)
Our stay at Topside Inn exceeded expectations. Christy provided exceptional service, preparing thoughtful birthday surprises for my mother and arranging a corner room with wonderful views. She also ensured my mother’s dairy allergy was carefully accommodated at breakfast. Her professionalism, warmth, and genuine care made our stay truly memorable. We look forward to returning.

Reviewed on May 19, 2026

Greenleaf Inn

Greenleaf Inn

2 out of 5
Price was $1,305, price is now $1,074 per person
$1,074
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
9.2/10 Wonderful! (15 reviews)
Our host is the best! Such a beautiful property.

Reviewed on Nov 16, 2025

Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

Hawthorn Extended Stay by Wyndham Ellsworth / Bar Harbor

3 out of 5
Price was $1,111, price is now $920 per person
$920
per person
Jul 7 - Jul 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
8.2/10 Very Good! (1,000 reviews)
Rooms were clean and neat.

Reviewed on May 23, 2026

Pressey House Lakeside Bed & Breakfast

Pressey House Lakeside Bed & Breakfast

3 out of 5
Price was $1,551, price is now $1,288 per person
$1,288
per person
Aug 1 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Augusta (AUG)
No reviews
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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
$139 nightly
The price is $151 total per night from Jun 7 to Jun 8
$151 total
Jun 7 - Jun 8
Total with taxes and fees
9.2/10 Wonderful! (1,004 reviews)
"Don't recommend trying to reach out to hotel through third party booking app as they are not responsive, and the cancelation policy is strict, with no room for grace, so buyer beware. No problem charging for a room not checked in to, no refunds, no exceptions. Says alot about customer service."

Reviewed on May 27, 2026

Maine Evergreen Hotel, an Ascend Collection Hotel
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
$105 nightly
The price is $114 total per night from May 31 to Jun 1
$114 total
May 31 - Jun 1
Total with taxes and fees
8.6/10 Excellent! (930 reviews)
"Clean hotel with comfortable rooms although a bit noisy. Lobby is in a weird location on 2nd floor a quite a way from elevator or stairs. Free breakfast in the morning was pretty good and servers were excellent."

Reviewed on May 25, 2026

Holiday Inn Express & Suites Waterville - North by IHG
Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

2 out of 5
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $119 total per night from May 31 to Jun 1
$119 total
May 31 - Jun 1
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
"Clean room. Nice breakfast."

Reviewed on May 26, 2026

Fireside Inn & Suites Waterville
See all 697 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 $533 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.