Windsor Vacation Packages
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Your Windsor Vacation
Enjoy amazing adventures when you reserve a Windsor vacation package. Whether you're a history buff, foodie or just a traveler who loves discovering new places, there's something for everyone in this awesome city. If seeing the sights is a priority during your trip to Windsor, make sure you swing by popular attractions like Wahconah Falls State Park and Bas Ridge Golf Course. No matter your travel plans or the size of your budget, organizing a tailored Windsor vacation is a walk in the park with Expedia.
Top Windsor Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Weathervane Motel
CA $1,024
per person
Sep 17 - Sep 23
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
6.8/10 (790 reviews)
The room was clean, but very run down — soft uneven floors, very out of date decor, musty smell.
Staff is courteous and helpful.
Air conditioning was cold and effective. Water pressure strong, hot water plentiful.
Parking was ample.
The environment felt safe, as does most of Vermont, but the door lock was old and not strong, I didn’t leave any valuables in the room while I was out. And the security deadbolts did not work at all.
I probably wont stay there again as there are better options similarly priced in the area. But if you have to, it’s at least clean.
Reviewed on Aug 10, 2026
The White House Inn
CA $1,473
per person
Sep 24 - Sep 27
just found
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
9/10 Wonderful! (340 reviews)
This is a beautiful property with a clean and friendly staff. Impeccably maintained! The dinner we had in the dining room was excellent. The only complaint I have is that my room could have used another bar of soap, and that's no biggie!
Reviewed on Aug 9, 2026
The Palmer House Resort, an Ascend Collection Hotel
CA $1,369
per person
Sep 24 - Sep 27
just found
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
8.2/10 Very good! (983 reviews)
Property is very run down. Our room was filthy. Bedding stained, toilet seat stained and floor was extremely dirty. My kids were very much looking forward to the fishing pond advertised as an amenity. Unfortunately the dock was sinking, a rowboat was full of water and beer cans, and the pond was covered entirely in weeds. We didn’t even stay the night.
Reviewed on Aug 9, 2026
Ready to book your vacation to Windsor?
Windsor Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
CA $131
CA $162 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (2,516 reviews)
"Great area...reasonable, very clean and cosy... Highly recommended"
Reviewed on Aug 9, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
CA $198
CA $221 total
Aug 12 - Aug 13
includes taxes & fees
9.2/10 Wonderful! (1,020 reviews)
"Room was clean. Staff friendly and helpful. Breakfast was adequate, nothing fancy, but serviceable with bagels, yogurts, "eggs". The breakfast staff was very attentive though. Outside pool was very nice. Could have used some more poolside umbrellas for the sun. Indoor pool was like a sauna due to ..."
Reviewed on Aug 10, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
CA $132
CA $178 total
Aug 31 - Sep 1
includes taxes & fees
9/10 Wonderful! (1,059 reviews)
"Great, spacious accommodation near many things and perfect for Tanglewood concert. Loved the room, the coffee in the lobby, and all the amenities. Would stay again and again"
Reviewed on Aug 9, 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?
Offering great value package deals from CA $1,024 on Expedia, you'll be pleasantly surprised at how much a vacation to Windsor costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Windsor?
You can typically find lower prices and greater availability in January, February and March. Explore our cheap Windsor vacation packages and you could land some great off-season discounts.
How many days is enough for Windsor?
With a well-organized itinerary, you can easily tick off the top Windsor attractions in a handful of days. But if you want to discover hidden gems or go on day trips, think about booking your Windsor vacation for longer.
How to find the best Windsor package deals?
Begin your search for a Windsor package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Windsor package deal straight away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Windsor adventure off to a flying start.
Is it cheaper to book a Windsor vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and stays individually. Better still, you can personalize your Windsor trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Windsor?
If you've got your Windsor travel dates locked in, book as early as you can to grab some unbeatable deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Windsor?
- Choose when to go: Check your diary and get packing. Your favourite time of year and the activities on offer will also help you decide when to visit Windsor.
- Work out your budget: Make sure you have enough money to cover everything from transportation and dining out to flights and activities. Your accommodations will probably be the largest expense during your trip to Windsor.
- Decide how long to go away for: Now that you're more familiar with Windsor, you can figure out the ideal length of your break. Create a rough plan and allocate enough time to cover everything you want to see.
- Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find a Windsor vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
