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.
Westwinds Waterfront Resort
CA $1,087
per person
Nov 26 - Dec 3
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9/10 Wonderful! (737 reviews)
Excellent time at this property. Only thing I wish was a little bit later checkout time as our flight wasn’t until 9pm at night and we had to be out by 10am. I understand it was most likely due to cleaning for incoming guest so we made it work. Overall I would definitely stay at this property again if we ever returned to Clearwater.
Reviewed on Oct 15, 2026
Ocean Club Treasure Island Hotel
Sunshine Beach
CA $1,738
per person
Nov 25 - Nov 30
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,252 reviews)
Very clean place, great staff but had bathroom issues which they will fix! But overall good.
Reviewed on Oct 16, 2026
Anna Maria Beach Resort
CA $4,670
per person
Nov 24 - Nov 29
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.4/10 Exceptional! (423 reviews)
We loved the Anna Maria Beach Resort and plan on returning for another vacation!
Reviewed on Oct 15, 2026
Sunrise Garden Resort
CA $2,203
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
4/10 (2 reviews)
The hotel was conveniently located near the beach and restaurants. The interior and exterior were immaculately clean, and the pool was a lovely feature. It was a peaceful and relaxing getaway.
Reviewed on Oct 15, 2026
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
Bayonet Point
1 out of top 10 points of interest in this area
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.
Gulf Shores
Gulf Shores might not have many top sights, but Hudson Beach and Show Palace Dinner Theater are two attractions nearby that you can check out.
Hudson Beach Estates
1 out of top 10 points of interest in this area
Though Hudson Beach Estates might not have many top sights, you can venture to the surrounding area to see attractions like Hudson Beach and Show Palace Dinner Theater.
Sea Ranch
While Sea Ranch isn't home to many top sights, Hudson Beach and Show Palace Dinner Theater are some notable places to visit nearby.
Gulf Coast Acres
2 out of top 10 points of interest in this area
While visiting Gulf Coast Acres, you might make a stop by sights like Show Palace Dinner Theater and Colorama Music.
Windsor Mill Hotel Deals
La Vista Inn
11736 US HIGHWAY 19 Port Richey FL
Fully refundableReserve now, pay when you stay
CA $89
CA $100 total
Nov 16 - Nov 17
includes taxes & fees
Motel 6 Spring Hill, FL - Weeki Wachee
6172 Commercial Way Spring Hill FL
Fully refundableReserve now, pay when you stay
CA $75
CA $83 total
Oct 22 - Oct 23
includes taxes & fees
7.4/10 Good! (1,593 reviews)
"We had a really big room, but did not have a microwave or a fridge inside which we thought it was really weird. I think the thing that bothered us the most we had roaches as soon as you put on the lights, you saw three roaches in the bathroom one walking over the TV it’s a really nice big place. ..."
Reviewed on Oct 16, 2026
Quality Inn & Suites Tarpon Springs South
38724 US Highway 19 North Tarpon Springs FL
Fully refundable
CA $113
CA $128 total
Oct 25 - Oct 26
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 Mill vacation package cost?
We make it easy to travel somewhere new, with Windsor Mill packages starting from as little as CA $953. 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.
Things to do
Clear Kayak Tours in Weeki Wachee
CA $111
per adult
100% of travellers recommend
Audio Guide to New Port Richey's History and Quirky People
CA $10
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.