Windsor Vacations from $387

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The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Mid-Town Motel

Mid-Town Motel

2 out of 5
Price was $460, price is now $387 per person
$387
per person
Jun 1 - Jun 5
found 4 hours ago
Roundtrip flight included
Chicago (ORD) to Augusta (AUG)
8.8/10 Excellent! (214 reviews)
I was in room #2 The room was big, bed was comfortable, water was hot and good pressure. Great distance for walking to town. The windows were open when I arrived, nice breeze but the cigarette smell from the neighbor not so enjoyable. A fridge would have been nice in the room As would have coffee (waiting on office for others to make theirs was not enjoyable) WALLS are paper thin. You can hear everything. Towels ( face towel in particular) had brown stains on them

Reviewed on Oct 20, 2025

Bluebird Ocean Point Inn

Bluebird Ocean Point Inn

3 out of 5
Ocean Point
Price was $1,166, price is now $953 per person
$953
per person
Jun 28 - Jul 3
found 9 hours ago
Roundtrip flight included
Dallas (DFW) to Augusta (AUG)
8.8/10 Excellent! (556 reviews)
Thank you for another great stay, 37 years and counting! Clean updated rooms, friendly staff, morning coffee and the most amazing key lime pie on the planet.

Reviewed on Oct 23, 2025

Hampton Inn Ellsworth/Bar Harbor

Hampton Inn Ellsworth/Bar Harbor

2.5 out of 5
Price was $889, price is now $733 per person
$733
per person
Jun 30 - Jul 3
found 1 day ago
Roundtrip flight included
New York (NYC) to Augusta (AUG)
9.2/10 Wonderful! (1,001 reviews)
This is absolutely a beautiful hotel with very friendly staff. I have nothing negative to add. We will definitely be returning in November, staying a few days in Bar Harbour MI, on our way to Florida. KarenLee checked us in & she was wonderful. Thanks for a beautiful place to stay.

Reviewed on Apr 10, 2026

OneSixtyFive

OneSixtyFive

3 out of 5
Price was $1,506, price is now $1,242 per person
$1,242
per person
Jun 29 - Jul 6
found 4 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Augusta (AUG)
9.4/10 Exceptional! (149 reviews)
Wonderful property, quiet comfortable rooms, friendly staff, great location in Brunswick, definitely worth staying for the delicious breakfast too,

Reviewed on Mar 12, 2026

Spruce Point Inn

Spruce Point Inn

3.5 out of 5
Save 100% on your flight
Price was $2,589, price is now $2,153 per person
$2,153
per person
Jun 29 - Jul 6
found 4 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Augusta (AUG)
8.8/10 Excellent! (397 reviews)
didn't have breakfast but view was amazing

Reviewed on Oct 23, 2025

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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
$127 nightly
The price is $138 total per night from May 17 to May 18
$138 total
May 17 - May 18
Total with taxes and fees
9.2/10 Wonderful! (1,003 reviews)
Exceeded our expectations. The rooms were nice and clean, organic coffees and breakfast were a nice touch. Staff were available when needed and friendly, always professional. Overall the stay was completely positive.

Reviewed on Apr 26, 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
$96 nightly
The price is $105 total per night from May 3 to May 4
$105 total
May 3 - May 4
Total with taxes and fees
8.6/10 Excellent! (904 reviews)
Very clean, well kept and stylish facility. Room was spacious and well thought through in design. Very comfortable. Staff was also excellent. Welcoming and accommodating. Also has an exercise room and indoor pool for customers.

Reviewed on Apr 22, 2026

Holiday Inn Express & Suites Waterville - North by IHG
Senator Inn & Spa

Senator Inn & Spa

3 out of 5
284 Western Ave Augusta ME
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $132 total per night from Apr 30 to May 1
$132 total
Apr 30 - May 1
Total with taxes and fees
7.8/10 Good! (1,002 reviews)
The Spa is wonderful!

Reviewed on Apr 26, 2026

Senator Inn & Spa
See all 664 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 $387 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.