Windsor Vacations from $474
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
The Brunswick Hotel
$1,008
per person
Oct 22 - Oct 26
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Augusta (AUG)
9.4/10 Exceptional! (1,006 reviews)
Excellent location. Right across street from the train station. Easy walk to downtown restaurants and quaint shops. Gorgeous outdoor space with fire pit. Several places to sit and relax or play games in the lobby or on the covered porch. Staff was extremely friendly and available. Rooms were immaculate and had all amenities needed.
Reviewed on Sep 17, 2026
Stone Park
$616
per person
Nov 4 - Nov 7
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Augusta (AUG)
9.4/10 Exceptional! (332 reviews)
Great place to stay! Very clean! Bed is comfortable. Coffee cakes for breakfast were yummy. Close to Bar Harbor. The only thing: when you book, let them know if you have any limitations that may affect your ability to use stairs to get to the second or third floor. They do not have an elevator. Other than that we were super pleased with our stay and most definitely come back!
Reviewed on Sep 20, 2026
Windsor Hotel Deals
Maine Evergreen Hotel, an Ascend Collection Hotel
65 Whitten Rd Augusta ME
Fully refundable
$148 nightly
$161 total
Oct 18 - Oct 19
Total with taxes and fees
9.4/10 Exceptional! (1,002 reviews)
"Great spot,easy access off the highway,nice pub & eatery,great supper & breakfast,lots of hot water too,would return anytime"
Reviewed on Sep 18, 2026
Fireside Inn & Suites Waterville
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
$117 nightly
$128 total
Oct 4 - Oct 5
Total with taxes and fees
Senator Inn & Spa
284 Western Ave Augusta ME
Fully refundableReserve now, pay when you stay
$128 nightly
$140 total
Oct 19 - Oct 20
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
"Clean room, excellent staff. Restaurant and fitness equipment were a nice surprise."
Reviewed on Sep 19, 2026
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 |
More vacations you might like
Frequently asked questions
How much does a Windsor vacation package cost?
You'll find cheap prices from $474 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.
Explore a world of travel with Expedia
- Augusta Hotels
- Cottages in Chelsea
- Hotels with a Pool in Chelsea
- Cottages in Somerville
- 3 Star Hotels in Windsor
- Hallowell Hotels
- Bangor Hotels
- Pet-Friendly Hotels in Augusta
- Camden Hotels
- Chelsea Hotels
- Portland Hotels
- Waterville Hotels
- Cottages in South China
- Cottages in Windsor
- Rockland Hotels
- Cheap Hotels in Augusta
- Boothbay Harbor Hotels
- Houseboats in Augusta
- B&B in Windsor
- Motels in South China
- Belfast Hotels
- Coopers Mills Hotels
- 4 Star Hotels in Somerville
- Gardiner Hotels
- Windsor Hotels
- B&B in Somerville
- South China Hotels
- B&B in South China
- B&B in Chelsea
- Jefferson Hotels
- Motels in Windsor
- Vacation Homes in Coopers Mills
- Brunswick Hotels
- Apartments in Somerville
- Cabin Rentals in Chelsea
- Vacation Homes in Windsor
- Cabin Rentals in Augusta
- Cabin Rentals in Windsor
- Condo Rentals in South China
- Rv Parks in South China
- Houseboats in Chelsea
- Hotels with an Indoor Pool in Augusta
- Flights from Windsor
- Flights from Augusta State
- Flights from Bangor Intl.
- Flights from South China
- Flights from Boston (BOS) to Augusta (AUG)
- Flights to Windsor
- Flights from Portland Intl. Jetport
- Flights to Chelsea
- Flights from Los Angeles (LAX) to Augusta (AUG)
- Flights to Bangor
- Flights from Chelsea
- Flights from San Antonio (SAT) to Augusta (AUG)
- Flights from Atlanta (ATL) to Augusta (AUG)
- Flights to Portland
- Flights to South China
- Flights to Augusta
- First Congregational Church
- Camden Vacations
- Augusta Mill Park
- Manchester Vacations
- Visit South China
- Jefferson Vacations
- Visit Coopers Mills
- Blaine House
- Waterville Vacations
- Redington Museum
- Capitol Park
- Turnpike Mall
- Holocaust Human Rights Center of Maine
- Colby College
- China Vacations
- Natanis Golf Course
- Oakland Vacations
- Rome Vacations
- Pine Tree State Arboretum
- Liberty Tool Company
- Kennebec Arsenal
- Ll Bean Flagship Store
- Maine State House
- Governor Hill Mansion
- Old Fort Western
- Visit Augusta
- Cushnoc Archeological Site
- Union Vacations
- Old Federal Building
- Augusta Vacations
- Kennebec River
- Maine Veterans Memorial Cemetery
- Harlow Gallery
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
