Windsor Vacations from $1,178

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The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Comfort Inn Ellsworth - Bar Harbor

Comfort Inn Ellsworth - Bar Harbor

2.5 out of 5
Price was $1,499, price is now $1,178 per person
$1,178
per person
Jul 18 - Jul 25
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Augusta (AUG)
9/10 Wonderful! (956 reviews)
Breakfast was free and staff was very friendly

Reviewed on Apr 23, 2026

Bluebird Ocean Point Inn

Bluebird Ocean Point Inn

3 out of 5
Ocean Point
Price was $1,906, price is now $1,411 per person
$1,411
per person
Jul 18 - Jul 25
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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

Topside Inn

Topside Inn

3 out of 5
Save 100% on your flight
Price was $1,870, price is now $1,392 per person
$1,392
per person
Jul 2 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
10/10 Exceptional! (88 reviews)
The views were incredible

Reviewed on Oct 26, 2025

Greenleaf Inn

Greenleaf Inn

2 out of 5
Save 100% on your flight
Price was $2,409, price is now $1,838 per person
$1,838
per person
Jul 18 - Jul 25
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Augusta (AUG)
9.2/10 Wonderful! (15 reviews)
Our host is the best! Such a beautiful property.

Reviewed on Nov 16, 2025

House near Acadia National Park

House near Acadia National Park

4 out of 5
Save 100% on your flight
Price was $3,372, price is now $2,654 per person
$2,654
per person
Jul 18 - Jul 25
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Augusta (AUG)
9.8/10 Exceptional! (24 reviews)
My family enjoyed our time at this property. I received a friendly email prior to arrival with clear directions and local recommendations. It is a beautiful house, nicely decorated with comfortable furniture - perfect for relaxing and visiting. We loved the location, it is in a quiet neighborhood with multiple shopping and dining options nearby. It took us about 35 minutes to drive to the Bar Harbor area.

Reviewed on Oct 15, 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
The price is $139 total per night from May 31 to Jun 1
$139 total
per night
May 31 - Jun 1
9.2/10 Wonderful! (1,000 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
The price is $105 total per night from May 17 to May 18
$105 total
per night
May 17 - May 18
8.6/10 Excellent! (906 reviews)
Breakfast food and staff fabulous! Rooms a little dated, but they really make up for it in cleanliness and friendlyness.

Reviewed on Apr 30, 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
The price is $143 total per night from May 3 to May 4
$143 total
per night
May 3 - May 4
7.8/10 Good! (1,002 reviews)
The Spa is wonderful!

Reviewed on Apr 26, 2026

Senator Inn & Spa
See all 662 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 $1,178 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.