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.
210 Main St
CA $795
per person
Oct 24 - Oct 26
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Augusta (AUG)
9.4/10 Exceptional! (14 reviews)
It was unclear to me, that this was a Big house and a rental of rooms. Total of 7 rooms/suites. Vintage decor with easy keypad entry and a HUGE tv. House not Handicap accessible, from what I could see. We had to carry our luggage up a flight of stairs. That also was not made clear. No amenities other than a small area for laundry. Quarters only. Very close for walking downtown. Coffee place nearby, a plus. I would stay here again. Good AC and WiFi.
Reviewed on Aug 21, 2026
Bluebird Ocean Point Inn
Ocean Point
CA $1,053
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
8.8/10 Excellent! (609 reviews)
Arrived after 4 pm check in. Had to wait for room approximately a half hour while other couples came in and got room keys right away. ???. Bathroom sink was very small, Shower had half door. Floor got soaked. Hate to say it but won't go back
Reviewed on Aug 24, 2026
OneSixtyFive
CA $1,148
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Augusta (AUG)
9.4/10 Exceptional! (163 reviews)
Room could have been cleaner (stain on blanket, ceiling bath vent very layered in dust, stain on chair)
Our buildings hot water heater broke so there was no hot shower but they let me use another vacant rooms cleaned bathroom and offered us a discount on the rate
Reviewed on Aug 6, 2026
Ready to book your vacation to Windsor?
Windsor Hotel Deals
Maine Evergreen Hotel, an Ascend Collection Hotel
65 Whitten Rd Augusta ME
Fully refundable
CA $209
CA $228 total
Sep 13 - Sep 14
includes taxes & fees
9.2/10 Wonderful! (1,010 reviews)
"Clean hotel with very accommodating staff. Breakfast and coffee are very good"
Reviewed on Aug 26, 2026
Fireside Inn & Suites Waterville
376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
CA $175
CA $190 total
Sep 13 - Sep 14
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Rooms were clean, beds comfortable. Children enjoyed the pool. Disappointed that the hotel does not clean during multiple days stay."
Reviewed on Aug 25, 2026
Senator Inn & Spa
284 Western Ave Augusta ME
Fully refundableReserve now, pay when you stay
CA $195
CA $213 total
Aug 30 - Aug 31
includes taxes & fees
8/10 Very good! (1,026 reviews)
"A new vendor for hand soap should be on order"
Reviewed on Aug 22, 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.
Frequently asked questions
How much does a Windsor vacation package cost?
You can snap up a vacation package to this top destination from CA $795 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.
