Windsor Vacations from $636

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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 $800, price is now $636 per person
$636
per person
Jul 11 - Jul 15
found 9 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) to Augusta (AUG)
8.8/10 Excellent! (213 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 $1,238, price is now $972 per person
$972
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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

Red Cedar Haven in Sidney

Red Cedar Haven in Sidney

2 out of 5
Save 100% on your flight
Price was $3,224, price is now $2,539 per person
$2,539
per person
Jun 4 - Jun 10
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Augusta (AUG)
No reviews
Pressey House Lakeside Bed & Breakfast

Pressey House Lakeside Bed & Breakfast

3 out of 5
Price was $1,481, price is now $1,172 per person
$1,172
per person
Jun 4 - Jun 10
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Augusta (AUG)
No reviews
Gables End Cottage in Belgrade

Gables End Cottage in Belgrade

2 out of 5
Save 100% on your flight
Price was $3,593, price is now $2,876 per person
$2,876
per person
Jul 11 - Jul 15
found 5 hours ago
Roundtrip non-stop flight included
Indianapolis (IND) 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
$124 nightly
The price is $135 total per night from May 10 to May 11
$135 total
May 10 - May 11
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
There was no hot tub.

Reviewed on Apr 12, 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
$112 nightly
The price is $122 total per night from Apr 19 to Apr 20
$122 total
Apr 19 - Apr 20
Total with taxes and fees
7.8/10 Good! (1,011 reviews)
The hotel restaurant was fine - I had breakfast, and the menu consisted of typical breakfast fare. My meals were cooked properly and the service was very good. Cereal or oatmeal would have been nice. I received a call a week before my stay that yhe pool and hot tub would be vlosed for maintenence ...

Reviewed on Apr 13, 2026

Senator Inn & Spa
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 Apr 26 to Apr 27
$105 total
Apr 26 - Apr 27
Total with taxes and fees
8.6/10 Excellent! (897 reviews)
Breakfast pretty basic, hotel was clean, friendly staff

Reviewed on Apr 17, 2026

Holiday Inn Express & Suites Waterville - North by IHG
See all 669 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 $636 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.