Windsor Mill Vacation Packages

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Top Holiday Package Deals in Windsor Mill

Price found within the past 48 hours. Click for updated prices.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Price was CA $1,265, price is now CA $729 per person
CA $729
per person
Oct 18 - Oct 23
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (1,017 reviews)
Loved it Voco hotel was great clean and quiet great place to just sit back and relax place was not busy at all kids are all back in school thank god . Beach’s all near by 10 to 20 minute drive to any beach u wana go too.

Reviewed on Sep. 2, 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Price was CA $2,096, price is now CA $1,113 per person
CA $1,113
per person
Nov 8 - Nov 15
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.2/10 Wonderful! (1,056 reviews)
Hands down one of the best hotels I’ve ever stayed at. Not only is it in a gorgeous location but the suite was incredible, the wine that was waiting for us in our room was phenomenal and the amenities were wonderful. They offer bikes for free as part of your stay, and me and my daughter biked all around the island it was such a good day ☀️. Would absolutely recommend this place to anybody. Perfect for couples but also very family friendly too. Will be staying here again!!

Reviewed on Sep. 7, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Price was CA $2,441, price is now CA $1,352 per person
CA $1,352
per person
Nov 8 - Nov 15
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (618 reviews)
We were very pleased with our 3 night stay at the hotel. The staff graciously offered us an umbrella and chairs to take to the beach from the donation stash. We really appreciated that and returned the items when we left for future guests.

Reviewed on Sep. 8, 2025

La Tortuga

La Tortuga

4 out of 5
Pass-a-Grille
Price was CA $2,447, price is now CA $1,440 per person
CA $1,440
per person
Nov 8 - Nov 15
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (29 reviews)
Very beautiful. Quiet. Easy check in/ out. Would stay again. Only complaint is walls are thin, can hear your neighbors.

Reviewed on Apr. 11, 2025

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $2,381, price is now CA $1,457 per person
CA $1,457
per person
Nov 30 - Dec 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (446 reviews)
Nice. On the beach. Provided chairs, toys, and umbrellas for the beach daily. Perfect for families. Only con is there are no guest showers and late check outs are not avaliable. If you want to visit the beach on your last day there is no where for you to shower and change before heading to the airport. Our entire family of six was cramed into the second floor restroom with our luggage changing clothes. The floor was full of sand when we entered the restroom so it seems like everyone does the same thing. Would I stay there again ? Yes.

Reviewed on Sep. 6, 2025

Where to stay in Windsor Mill

Find the best Windsor Mill areas and neighborhoods for the activities you enjoy most. Learn more about Windsor Mill
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Bayonet Point

1 out of top 10 points of interest in this area
3.5/5(5 area reviews)

Shopping, waterfront views, and restaurants highlight some of the notable features of Bayonet Point. Make a stop by Beacon Woods Golf Course while you're exploring.

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Frequently asked questions

How much does a Windsor Mill vacation package cost?
We make it easy to travel somewhere new, with Windsor Mill packages starting from as little as CA $729. You'll have the flexibility to bundle your favorite hotels, airlines and car rental. For the ultimate escape, why not add some experiences and tours to your itinerary?
How do I get a cheap travel package to Windsor Mill?
Bundle, bundle, bundle. Hotels, flights and rental cars — combine whatever you need into a Windsor Mill vacation package and save. Score even more bargains when you include extras such as sightseeing tours to your booking. But that's not the only good part. You have the flexibility to customize your trip your own way. We offer over 550 air carriers and 1,000,000 hotel options throughout the world, so that everyone has a chance to travel and live out those vacation fantasies.
Where should I stay in Windsor Mill?
Close to the action. Many travelers favor hotels in the vicinity of top attractions, like Hudson Beach, Regional Medical Center Bayonet Point and Show Palace Dinner Theater.
How far in advance should I book my Windsor Mill vacation?
Travelers are generally able to compare international fares on Expedia within 12 months of departure. Booking late? With a bit of luck, it's still possible to purchase an affordable ticket just weeks before your flight.
What does an Expedia Windsor Mill travel package include?
From hotels and flights to car rentals, Expedia can help you craft a Windsor Mill package that's right for you. Heading off for a few weeks? Give some thought to a rental car, flight and hotel bundle. If you're taking a quick break, an airfare and hotel deal could be what you're after. Experiences can also be added once you've made your booking. Our packages make it a cinch to plan and save.
What should I know before booking a Windsor Mill travel package?
Whether it's relaxation or adventure you're seeking, a Windsor Mill vacation package lets you plan your escape your way. Plus, you'll get access to great discounts when you combine your hotel with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Windsor Mill Expedia vacation package?
You sure can. Expedia has access to more than 550 partner airlines worldwide, so pick the carrier that suits your travel needs.
If I'm not able to travel, can I cancel my Windsor Mill vacation package?
Because we know life can throw you a few curveballs, the answer is yes. For further details, head to our Customer Service Portal. But generally speaking, if you've booked your Windsor Mill vacation package in the last 24 hours, you may be able to cancel or change it without penalty. Your airline, hotel or car rental company may impose a fee if you made your booking a while ago.

Discover the most popular places to visit in Windsor Mill

Hudson Beach

Why not spend a carefree afternoon at Hudson Beach during your travels in Hudson? Amble around the area's parks or visit its shops.

Hudson Beach

Beacon Woods Golf Course

Enjoy a round of golf in Hudson at Beacon Woods Golf Course. Amble around this family-friendly area's waterfront and enjoy its top-notch restaurants.

Beacon Woods Golf Course

Colorama Music

You can make plans for a show at Colorama Music during your stay in Hudson. Amble around this family-friendly area's waterfront and enjoy its top-notch restaurants.

Colorama Music
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.