Winifred Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Winifred

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was CA $1,165, price is now CA $743 per person
CA $743
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
9/10 Wonderful! (3,629 reviews)
Todo estuvo muy bien,

Reviewed on Jun 21, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was CA $3,168, price is now CA $1,931 per person
CA $1,931
per person
Jul 28 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
9.2/10 Wonderful! (1,009 reviews)
The cottage was wonderful. Stocked with everything you need just bring your food, drink and toilet paper! The cottage we stayed at was a perfect location just 5 minute walk to the amazing pool complex. The resort is great. Planning on going back soon.

Reviewed on Jun 20, 2026

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was CA $2,848, price is now CA $1,891 per person
CA $1,891
per person
Aug 11 - Aug 18
found 18 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (550 reviews)
Esta bien Accesible a todas las amenidades, incluyendo el área de la playa,Solo que es un poco caro el precio por noche, por lo demás todo muy bien.

Reviewed on May 25, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $1,378, price is now CA $923 per person
CA $923
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.4/10 Very Good! (6,626 reviews)
I would definitely recommend remodeling the rooms.

Reviewed on Jun 21, 2026

Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Davis
Price was CA $1,376, price is now CA $930 per person
CA $930
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.4/10 Very Good! (1,881 reviews)
Staff was very kind.

Reviewed on Jun 21, 2026

Where to stay in Winifred

Find the best Winifred areas and neighborhoods for the activities you enjoy most. Learn more about Winifred
Lake Sumter Landing

Lake Sumter Landing

1 out of top 10 points of interest in this area

Though Lake Sumter Landing might not have many top sights, you can venture to the surrounding area to see attractions like The Villages Market Square and Cane Garden Country Club.

Find hotels in Lake Sumter Landing

Winifred Hotel Deals

FREE Golf Cart! Fabulous Location! Classy Decor! Pet-friendly!

FREE Golf Cart! Fabulous Location! Classy Decor! Pet-friendly!

The Villages FL
10/10 Exceptional! (60 reviews)
"Home was clean, everything was perfect!"

Reviewed on Mar 12, 2026

Get rates
FREE Golf Cart! Fabulous Location! Classy Decor! Pet-friendly!
Brownwood Hotel & Spa

Brownwood Hotel & Spa

3 out of 5
3003 Brownwood Blvd Wildwood FL
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from Jun 29 to Jun 30
CA $153
CA $164 total
Jun 29 - Jun 30
includes taxes & fees
9.8/10 Exceptional! (1,221 reviews)
"Best hotel in 50 miles. Great staff, nice clean rooms and property."

Reviewed on Jun 21, 2026

Brownwood Hotel & Spa
The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
The price is CA $139 per night from Jun 29 to Jun 30
CA $139
CA $148 total
Jun 29 - Jun 30
includes taxes & fees
9.2/10 Wonderful! (1,429 reviews)
"Safe environment, stunning location , lovely people, helpful staff. Will definitely stay here again."

Reviewed on Jun 21, 2026

The Waterfront Inn
See all 2,238 properties in Winifred
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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Winifred vacation package cost?
Get set to book, because a getaway to Winifred starts from a tempting CA $743. When you combine your hotels, flights and car rentals into a vacation package, you'll pick up the best prices.
How do I get a cheap travel package to Winifred?
If you love landing a bargain, bundle your bookings into a Winifred vacation package. Whether you need flights, hotels, day tours or rental cars, you can browse and book everything in one place. You'll have lots of choice at your fingertips as well. Expedia has more than 550 air carriers and 1,000,000 properties across the globe to take your pick of. Fly with who you want, find a room where you like and save a bundle — now that's the ideal vacation!
Where should I stay in Winifred?
With fascinating attractions such as The Villages Market Square and Cane Garden Country Club in this neighborhood, try to find a hotel near either of them. Glenview Champions Country Club is another Winifred sight that draws in the crowds.
What are the top hotels in Winifred?
Whether you'll be staying for one or several nights in Winifred, you'll get a wonderful night's rest at Beautiful 2/2 Dog - Friendly Villa Conviently Located W. This option is a favorite with lots of travelers.
How far in advance should I book my Winifred vacation?
Browse Expedia to compare international flights as early as possible. You can usually purchase a ticket up to a year prior to departure. If you can't see your preferred carrier, or you're booking late, don't stress. Cheap tickets to Winifred sometimes occur within weeks of departure.
What does an Expedia Winifred travel package include?
That depends on what you're after. If you're traveling by yourself, you might decide to combine hotels and flights. Bringing the entire family to Winifred? A travel package that includes hotels, flights and rental cars might be a better fit. Expedia gives you the flexibility and freedom to tailor-make your travel package.
What should I know before booking a Winifred travel package?
Whether it's adventure or relaxation you're craving, a Winifred vacation package lets you organize your escape your way. Plus, you'll score great discounts when you combine your accommodations with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a Winifred Expedia vacation package?
With a vacation package, you're the one in charge. Whether you're looking to fly to Winifred in first class or coach, simply pick from the available airline options. Expedia has access to more than 550 partner airlines around the world.
If I'm not able to travel, can I cancel my Winifred vacation package?
You can. We get that life happens, so we're here to help if you have to make changes to your Winifred vacation package. It may be possible to cancel or change your itinerary for free if you've booked within 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for further information. Also, be sure to check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Winifred

The Villages Market Square

4.5/5(2 reviews)

You can enjoy retail therapy at The Villages Market Square during your visit to The Villages. Wander the lakeside in this quaint area.

The Villages Market Square

Things to do

Gypsy Gold Horse Farm Tour

Gypsy Gold Horse Farm Tour

CA $76
per adult
100% of travellers recommend
Gypsy Gold Horse Farm Tour
See all activities in The Villages
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.