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.
EVEN Hotel Sarasota-Lakewood Ranch by IHG

EVEN Hotel Sarasota-Lakewood Ranch by IHG

3.5 out of 5
Price was CA $1,145, price is now CA $802 per person
CA $802
per person
May 24 - May 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.4/10 Very Good! (1,012 reviews)
The only issue we had was the breakfast. The hotel has only one staff attending to everyone, so when one is in a hurry, it can be frustrating to wait. But overall, staff is excellent the the hotel is clean.

Reviewed on Apr 19, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $2,575, price is now CA $1,734 per person
CA $1,734
per person
Jun 26 - Jul 1
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Tampa (TPA)
9.6/10 Exceptional! (889 reviews)
Very beautiful rooms, smart layout.

Reviewed on Apr 20, 2026

Delray House With Hot tub & Game Room

Delray House With Hot tub & Game Room

3.5 out of 5
Palm River-Clair Mel
Price was CA $1,812, price is now CA $1,287 per person
CA $1,287
per person
Jun 26 - Jul 1
found 14 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Tampa (TPA)
2/10 (3 reviews)
Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Price was CA $1,280, price is now CA $914 per person
CA $914
per person
May 24 - May 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.2/10 Very Good! (1,000 reviews)
No continental breakfast, front office wouldn’t break a $100 dollar bill saying they can’t accept them. Was no hot water but they had a plumber en route. They gave us coupons for a free breakfast but we were leaving. We stayed at two different Hiltons in two states and both were no more than average. I’ll opt for something different in the future

Reviewed on Apr 18, 2026

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $1,707, price is now CA $1,222 per person
CA $1,222
per person
May 29 - May 31
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Tampa (TPA)
9.4/10 Exceptional! (526 reviews)
This place is very nice and clean, my entire family loves it..we enjoyed our stay...

Reviewed on Apr 13, 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
Pirate ship at St Andrews State Park

Gulf Shores

Gulf Shores might not have many top sights, but Hudson Beach and Werner Boyce Salt Springs State Park are two attractions nearby that you can check out.

Find hotels in Gulf Shores

Windsor Mill Hotel Deals

Quality Inn & Suites Tarpon Springs South

Quality Inn & Suites Tarpon Springs South

2.5 out of 5
38724 US Highway 19 North Tarpon Springs FL
Fully refundable
The price is CA $154 per night from Apr 27 to Apr 28
CA $154
CA $174 total
Apr 27 - Apr 28
includes taxes & fees
8/10 Very Good! (1,079 reviews)
Room/facilities could have been cleaner. Overall a good stay for the money. Pool was nice.

Reviewed on Apr 21, 2026

Quality Inn & Suites Tarpon Springs South
Rodeway Inn Port Richey North

Rodeway Inn Port Richey North

2 out of 5
11810 Us Highway 19 Port Richey FL
Fully refundableReserve now, pay when you stay
The price is CA $87 per night from May 5 to May 6
CA $87
CA $101 total
May 5 - May 6
includes taxes & fees
7.8/10 Good! (1,013 reviews)
Easy to get to. Check in was easy. Exactly what I nexpected it to be of a budget hotel on US 19. Booked an accessable room as i have mobility issues and stepping onto a bath tub is a problem. I was put into a regular room on the second floor. If there was an elevator i did not find it. As i was only ...

Reviewed on Apr 20, 2026

Rodeway Inn Port Richey North
Comfort Inn & Suites New Port Richey Downtown District

Comfort Inn & Suites New Port Richey Downtown District

2.5 out of 5
6206 US HWY 19 New Port Richey FL
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from May 21 to May 22
CA $148
CA $166 total
May 21 - May 22
includes taxes & fees
9.2/10 Wonderful! (1,291 reviews)
Fantastic staff.

Reviewed on Apr 21, 2026

Comfort Inn & Suites New Port Richey Downtown District
See all 1,806 properties in Windsor Mill
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.
All Inclusive Vacations
All Inclusive Vacations
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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 $802. 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

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

Things to do

Clear Kayak Tours in Weeki Wachee

Clear Kayak Tours in Weeki Wachee

CA $123
per adult
100% of travellers recommend
Clear Kayak Tours in Weeki Wachee
See all activities in Hudson
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.