Windsor Vacations from $742

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Grand Summit Hotel

Grand Summit Hotel

3 out of 5
Save 100% on your flight
Price was $980, price is now $742 per person
$742
per person
Oct 25 - Nov 1
found 23 hours ago
Roundtrip flight included
Minneapolis (MSP) to Augusta (AUG)
8.2/10 Very Good! (274 reviews)
We love staying here every year for the TMC. It’s clean, comfortable, and friendly. The pool is great! The restaurant in the hotel, however, is always a disappointment. Food is ok, but service is poor.

Reviewed on Aug 20, 2025

Greenleaf Inn

Greenleaf Inn

2 out of 5
Price was $1,193, price is now $854 per person
$854
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Augusta (AUG)
9.4/10 Exceptional! (9 reviews)
The location and view of this property was excellent. The staff gave good dining recommendations. The fire pit at night with s’mores was nice. We were given a nice bouquet of flowers at time of check in. The morning breakfast was a bit different. The kitchen was stocked with eggs, cream cheese, yogurt and condiments and pastries. You were responsible to make your own breakfast in the kitchen.

Reviewed on Jul 23, 2025

Topside Inn

Topside Inn

3 out of 5
Price was $1,236, price is now $981 per person
$981
per person
Oct 4 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
10/10 Exceptional! (38 reviews)
A perfect stay for our mother-daughter trip! We look forward to a future stay.

Reviewed on Aug 19, 2025

House near Acadia National Park

House near Acadia National Park

4 out of 5
Price was $1,517, price is now $1,213 per person
$1,213
per person
Oct 25 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Augusta (AUG)
9.8/10 Exceptional! (19 reviews)
This was the perfect stay for our family of 8. The 3 bathrooms, well-stocked kitchen and laundry machines made everything very convenient and enjoyable versus all of us being separated in hotel rooms. The owner was super responsive to all of our questions. Location is perfect as it’s close to downtown Bar Harbor, Acadia National Park and is right by a beautiful river just down the street! Highly recommend this property.

Reviewed on Aug 23, 2025

Red Cedar Haven in Sidney

Red Cedar Haven in Sidney

2 out of 5
Save 100% on your flight
Price was $2,203, price is now $1,781 per person
$1,781
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Augusta (AUG)
No reviews
Don't see what you're looking for?
See all available trips from Columbus to Windsor
View all trips

Windsor Hotel Deals

Maine Evergreen Hotel, Ascend Hotel Collection

Maine Evergreen Hotel, Ascend Hotel Collection

2.5 out of 5
65 Whitten Rd, Augusta, ME
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $169 total per night from Sep 1 to Sep 2
$169 total
Sep 1 - Sep 2
Total with taxes and fees
9/10 Wonderful! (1,002 reviews)
"Great stay."

Reviewed on Aug 22, 2025

Maine Evergreen Hotel, Ascend Hotel Collection
Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

2 out of 5
376 Main Street, Waterville, ME
Fully refundableReserve now, pay when you stay
$146 nightly
The price is $159 total per night from Aug 24 to Aug 25
$159 total
Aug 24 - Aug 25
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
"Room was extremely clean! I didn't like that grab and go breakfast!"

Reviewed on Aug 21, 2025

Fireside Inn & Suites Waterville
The Elmwood

The Elmwood

2.5 out of 5
455 Kennedy Memorial Dr, Waterville, ME
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $162 total per night from Aug 24 to Aug 25
$162 total
Aug 24 - Aug 25
Total with taxes and fees
8.4/10 Very Good! (457 reviews)
"Amanda at check in was fantastic! Room recently refurbished, clean, and comfortable."

Reviewed on Aug 16, 2025

The Elmwood
See all 653 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Windsor vacation package cost?
You'll find cheap prices from $742 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.