Windsor Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
Top Windsor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Mid-Town Motel
CA $1,333
per person
Oct 10 - Oct 13
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Augusta (AUG)
8.6/10 Excellent! (268 reviews)
Cute spot, great way to save money versus staying right on the water, and still so close you don't miss anything! Bed was comfortable which is always a plus and the staff were so nice checking us in!
Reviewed on Aug 30, 2026
Bluebird Ocean Point Inn
Ocean Point
CA $1,568
per person
Oct 2 - Oct 5
just found
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
8.8/10 Excellent! (619 reviews)
Great spot right with amazing views and tranquil area. Convenient to have full service bar and restaurant on site. 15 min drive to downtown Booth Bay Harbor
Reviewed on Aug 30, 2026
Greenleaf Inn
CA $1,894
per person
Oct 10 - Oct 13
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Augusta (AUG)
9.6/10 Exceptional! (32 reviews)
This property is a MUST if you're in the Boothbay area! We really enjoyed everything about our stay! The room, the amenities, the service, the view, the treatment - it's DEFINITELY worth a visit!!
Reviewed on Aug 30, 2026
Ready to book your vacation to Windsor?
Windsor Hotel Deals
Fireside Inn & Suites Waterville
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
CA $177
CA $193 total
Sep 27 - Sep 28
includes taxes & fees
8.8/10 Excellent! (1,011 reviews)
"Rooms were very clean. Staff was very helpful."
Reviewed on Aug 31, 2026
Maine Evergreen Hotel, an Ascend Collection Hotel
65 Whitten Rd Augusta ME
Fully refundable
CA $210
CA $229 total
Sep 13 - Sep 14
includes taxes & fees
9.4/10 Exceptional! (1,009 reviews)
"Very clean rooms."
Reviewed on Aug 31, 2026
Senator Inn & Spa
284 Western Ave Augusta ME
Fully refundableReserve now, pay when you stay
CA $195
CA $212 total
Sep 30 - Oct 1
includes taxes & fees
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.
Frequently asked questions
How much does a Windsor vacation package cost?
You can snap up a vacation package to this top destination from CA $1,333 on Expedia. However, how much your vacation to Windsor costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Windsor?
If you'd like to book a cheap Windsor vacation package, consider planning a trip in January, February and March. You'll usually find better prices on hotels and flights during these months — perfect for budget-conscious travellers.
How many days is enough for Windsor?
With a well-organized itinerary, you can easily visit the top Windsor sights in a few days. But if you'd like to discover hidden gems or go on day tours, consider booking your Windsor vacation for longer.
How to find the best Windsor package deals?
Use Expedia's filters to find some great Windsor package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Windsor package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Windsor vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component individually. And you'll still have the freedom to create a personalized Windsor vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Windsor?
If you're planning a spur-of-the-moment Windsor adventure, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score terrific deals on your flights and hotels by booking well in advance.
How to plan a trip to Windsor?
- Choose your dates: What you'd like to do in Windsor and your preferred season will help you decide when to travel.
- Plan your budget wisely: Besides the price of your stay, you should factor in other expenses. These include food, flights and transportation. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Windsor.
- Decide how many days away: Start by compiling a list of the activities and attractions you want to experience in Windsor. Then, estimate how long you'll need for each, along with any travel time.
- Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to choose a Windsor vacation package that brings all your bookings together.
Explore a world of travel with Expedia
- Manchester Hotels
- Windsor Hotels
- Liberty Hotels
- Cheap Hotels in Augusta
- Winslow Hotels
- Skyview Treehouse Lakefront Private Hot Tub
- Waterville Hotels
- Bangor Hotels
- Gardiner Hotels
- Pittston Hotels
- Washington Hotels
- Pet-Friendly Hotels in Waterville
- Hallowell Hotels
- Hotels near Thomas College
- Fireside Inn & Suites Waterville
- China Hotels
- Condo Rentals in South China
- Accor Hotels in Augusta
- Hotels with a Pool in Alna
- Cheap Hotels in Sidney
- Whitefield Hotels
- Apartments in Chelsea
- Best Western Plus Waterville Grand Hotel
- Rv Parks in Chelsea
- Houseboats in Chelsea
- Golf Hotels in Augusta
- Pet-Friendly Hotels in Augusta
- Fairway Overnight & Extended Stay
- The Three Cornered Pond Retreat
- Hampton Inn Waterville
- Apartments in Windsor
- Holiday Inn Express & Suites Waterville
- Hotels with Kitchenettes in Manchester
- Luxury Hotels in Augusta
- Augusta Hotels
- Lake Camp on Sheepscot Lake
- Apartments in Augusta
- Maine Evergreen Hotel
- Houseboats in Alna
- 4 Star Hotels in Belgrade
- Hotels with Waterslides in Augusta
- Tiny House with private hot tub on 100 acres
- Hotels with a Pool in Augusta
- Portland Hotels
- Flights from Moncton (YQM) to Augusta (AUG)
- Flights from Bangor Intl.
- Flights from Edmonton (YEG) to Augusta (AUG)
- Flights to Augusta
- Flights from London (LHR) to Waterville (WVL)
- Flights from Robert Lafleur
- Flights from Montreal (YUL) to Augusta (AUG)
- Flights from Plattsburgh (PBG) to Augusta (AUG)
- Flights from Detroit (DTW) to Waterville (WVL)
- Flights from Atlanta (ATL) to Augusta (AUG)
- Flights from Halifax (YHZ) to Augusta (AUG)
- Flights from Saskatoon (YXE) to Augusta (AUG)
- Flights from Manchester
- Flights from St. John's (YYT) to Augusta (AUG)
- Flights from Hagerstown (HGR) to Augusta (AUG)
- Flights from Augusta State
- Flights from Buffalo (BUF) to Augusta (AUG)
- Flights from Calgary (YYC) to Augusta (AUG)
- Flights from Winnipeg (YWG) to Augusta (AUG)
- Flights from Miami (MIA) to Augusta (AUG)
- Flights from Vancouver (YVR) to Augusta (AUG)
- Flights from Toronto (YYZ) to Augusta (AUG)
- Pemaquid Point Lighthouse Park
- Masonic Hall
- Fort Knox State Historic Site
- Portland Vacations
- Friendship Vacations
- Bailey Island Vacations
- Desert of Maine
- Poland Vacations
- Augusta Vacations
- Peru Vacations
- Bangor Vacations
- Casco Vacations
- Popham Beach State Park
- Monhegan Island Vacations
- Barrett's Cove Public Beach
- Durham Vacations
- East End Beach
- Camden Vacations
- Norway Vacations
- Fort Edgecomb State Historical Site
- Ll Bean Flagship Store
- Portland Head Light
- Rockland Harbor Park
- Freeport Vacations
- Coastal Maine Botanical Gardens
- Rockland Vacations
- Lewiston Vacations
- Samoset Resort Golf Course
- China Vacations
- Visit Augusta
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
