Winter Haven Vacation Packages

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Your Winter Haven Vacation

When a city getaway is calling, answer it with a Winter Haven vacation package. The neighborhood of Fussels Corner, which is great for golfing, nature and walking, makes a fantastic base for your adventures. You'll want to take in some sights during your trip to Winter Haven. Carve out some time for popular attractions like LEGOLAND® Florida, Chain of Lakes Park and Auburndale City Park. Don't put off visiting this destination any longer. The perfect Winter Haven vacation is just a few clicks away with Expedia.

Top Winter Haven Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

4 out of 5
Downtown Tampa
Save 100% on your flight
per person
Jul. 25 - Jul. 30
found 12 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
7.6/10 Good! (1,005 reviews)
Completely remodeled- looks great!

Reviewed on Jun. 1, 2024

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

Saddlebrook Golf Resort & Spa Tampa North - Wesley Chapel

4 out of 5
Wesley Chapel South
Save 100% on your flight
per person
Jul. 25 - Jul. 30
found 12 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
6.8/10 (1,004 reviews)
Beautiful grounds. Rooms were clean and spacious. Would stay here again

Reviewed on May 29, 2024

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Aug. 7 - Aug. 12
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Tampa (TPA)
9.6/10 Exceptional! (302 reviews)
The property was really nice. It was across the street a park that the up-keeping was not that great.

Reviewed on May 27, 2024

Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Westshore
Save 100% on your flight
per person
Jul. 25 - Jul. 30
found 12 hours ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9/10 Wonderful! (1,244 reviews)
We had a maintenance issue with the toilet continuously running and the tech came and changed the toilet assembly incorrectly with problem not being resolved. He also did not return the toilet tank cover back on the toilet properly and it was hanging off the side of the toilet. When we arrived there was trash on the common area floors and the trash can near the elevator was overflowing. We checked out 4 days later and the same trash was on the floor and the trash can was still overflowing.

Reviewed on Jun. 3, 2024

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Jul. 21 - Jul. 27
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Tampa (TPA)
8.8/10 Excellent! (1,000 reviews)
Lively motel with great location and access to the beach. Friendly staff. Kitchenette is great convenience. Would stay again.

Reviewed on Jun. 2, 2024

Winter Haven Hotel Deals

Best Western Plus Winter Haven Inn & Suites 
Best Western Plus Winter Haven Inn & Suites 
2.5 out of 5
5801 Roosevelt Dr, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is CA $173 per night from Jun. 11 to Jun. 12
CA $173
CA $193 total
includes taxes & fees
Jun 11 - Jun 12
9.2/10 Wonderful! (356 reviews)
"Great location , down the street from LEGOLAND & friendly staff."

Reviewed on Jun. 3, 2024

Best Western Plus Winter Haven Inn & Suites 
Holiday Inn Winter Haven, an IHG Hotel
Holiday Inn Winter Haven, an IHG Hotel
3 out of 5
200 Cypress Gardens Boulevard, Winter Haven, FL
Fully refundable
The price is CA $150 per night from Jun. 9 to Jun. 10
CA $150
CA $168 total
includes taxes & fees
Jun 9 - Jun 10
8.8/10 Excellent! (958 reviews)
"The staff were really attentive and plesant. My husband really liked that they were very easy to access and ask for coffee. The water pressure was a little weak and there were cracks in door where it looks like someone had pounded on it in the bathroom. When I told front desk they offered to move ..."

Reviewed on May 25, 2024

Holiday Inn Winter Haven, an IHG Hotel
Howard Johnson by Wyndham Winter Haven FL
Howard Johnson by Wyndham Winter Haven FL
2 out of 5
1300 3rd St Sw, Cypress Gardens & US 17 South, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is CA $127 per night from Jun. 9 to Jun. 10
CA $127
CA $143 total
includes taxes & fees
Jun 9 - Jun 10
6.8/10 (1,004 reviews)
Cute retro roadside inn
"I've stayed here a couple of times, and I love the retro feel of this cute little roadside inn. It's been well-maintained and has such adorable vibes I had my friends come to visit and stay here, as well. It's not fancy, but it's roomy, clean, and fun."

Reviewed on May 31, 2024

Howard Johnson by Wyndham Winter Haven FL
See all 39,113 properties in Winter Haven
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 Winter Haven vacation package cost?
Maybe less than you might think — from just CA $557, actually! By bundling flights, hotels and car rentals into your own custom-built package, your Winter Haven escape is just a few clicks away.
How do I get a cheap travel package to Winter Haven?
One of the simplest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities — we’ve got them all covered. Select a combination that best fits you and see your savings pile up. We know a package deal is never a one-size-fits-all. That’s why we offer more than 550 airlines and 1,000,000 hotel options worldwide, which lets you customize your Winter Haven adventure.
Where should I stay in Winter Haven?
If this is your first visit to Winter Haven, you’ll love Cypress Gardens. This vibrant neighborhood is home to some excellent attractions, such as LEGOLAND® Florida.
What are the top hotels in Winter Haven?
If you’re thinking of staying in the Cypress Gardens neighborhood, some great options are Winter Haven Gardens Inn and Holiday Inn Winter Haven, an IHG Hotel. Jan Phyl Village is also a popular Winter Haven area. We recommend Courtyard by Marriott Winter Haven or Econo Lodge Winter Haven Chain Of Lakes if you choose this end of town.
How far in advance should I book my Winter Haven vacation?
Be rewarded with the biggest variety and the cheapest prices by booking your vacation to Winter Haven nice and early. Airlines tend to release flight tickets around 12 months before departure, so reserve your spot as soon as possible. That said, Expedia is committed to giving you the best bargains around, so it’s always a good time to book your dream vacation!
What does an Expedia Winter Haven travel package include?
Travel packages include flights, hotels and rental cars, but you can combine any of them to create your dream Winter Haven vacation. You can also add on fun things like tours and activities once you’ve made your booking. You’re the boss! When you bundle your bookings with Expedia, you’ll get access to discounts you won’t find anywhere else.
What should I know before booking a Winter Haven travel package?
So many places to wander around, so many things to see. With a package, you’ll be able to check more of them off your list. Combine your flights, hotels and rental cars and land big savings.
Can I choose my airline with a Winter Haven Expedia vacation package?
Yes, and with over 550 airlines to choose from globally, you’re spoiled for choice. Browse the available options and see which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Winter Haven vacation package?
Yes you can, and we’ll help you every step of the way. You may be able to amend or cancel your Winter Haven vacation package at no cost within 24 hours of booking. But you may be charged a fee by your hotel, airline or car rental company if your booking is older than that. If your travel plans unexpectedly change, take a look at our Customer Service Portal for further information.

Discover the most popular places to visit in Winter Haven

Image for LEGOLAND® Florida

LEGOLAND® Florida

4.5/5(72 reviews)

Take the kids to this dynamic theme park for a day full of exciting rides, LEGO® brick creations and the chance to build your own LEGO®robots.

LEGOLAND® Florida
Image for Chain of Lakes Park

Chain of Lakes Park

3/5(1 review)

Catch an event at Chain of Lakes Park during your trip to Winter Haven. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.

Chain of Lakes Park
Image for Winter Haven Hospital

Winter Haven Hospital

Though Winter Haven Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Winter Haven while you are here.

Winter Haven Hospital

What to do in Winter Haven

Image for One hour Historical Wildlife Boat Cruise of The Chain of Lakes

One hour Historical Wildlife Boat Cruise of The Chain of Lakes

CA $36
Per adult
100% of travellers recommend
One hour Historical Wildlife Boat Cruise of The Chain of Lakes
Image for 2 Hour Historical Wildlife Tour of the Chain of Lakes

2 Hour Historical Wildlife Tour of the Chain of Lakes

CA $56
Per adult
2 Hour Historical Wildlife Tour of the Chain of Lakes
Image for 1 Hour Historical Wildlife Tour of The Famous Chain of Lakes

1 Hour Historical Wildlife Tour of The Famous Chain of Lakes

CA $36
Per adult
1 Hour Historical Wildlife Tour of The Famous Chain of Lakes
See all activities in Winter Haven

Other vacations you might like

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