Winter Haven Vacations from $550

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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.

The Latest Winter Haven vacation packages

Price found within the past 48 hours. Click for updated prices.
Ocean Club Treasure Island Hotel
voco Sarasota by IHG
The Westin Sarasota
Hibiscus Suites - Gateway to Siesta Key
Embassy Suites by Hilton Sarasota, FL
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See all available trips from Columbus to Winter Haven
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Discover the most popular places to visit in Winter Haven

What to do in Winter Haven

Winter Haven Hotel Deals

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG

3 out of 5
305 5th St NW and Avenue D NW, Winter Haven, FL
Fully refundable
$127 nightly
The price is $142 total per night from Aug 12 to Aug 13
$142 total
Aug 12 - Aug 13
Total includes taxes and fees
9.6/10 Exceptional! (485 reviews)
"Spacious rooms"

Reviewed on Aug 8, 2025

Staybridge Suites Winter Haven Auburndale by IHG
Holiday Inn Winter Haven by IHG

Holiday Inn Winter Haven by IHG

3 out of 5
200 Cypress Gardens Boulevard, Winter Haven, FL
Fully refundable
$93 nightly
The price is $104 total per night from Aug 17 to Aug 18
$104 total
Aug 17 - Aug 18
Total includes taxes and fees
8.8/10 Excellent! (1,000 reviews)
Excellent hotel
"This holiday Inn property was wonderful. Checkin was simple ,easy and I was given free food vouchers for my daughter for breakfast and dinner (with 1 adult paying adult. The breakfast was a full breakfast with all variety of items;Well worth it. Our room was clean and very spacious (1king bed & daybed ..."

Reviewed on Aug 6, 2025

Holiday Inn Winter Haven by IHG
Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 

3.5 out of 5
5801 Roosevelt Dr, Winter Haven, FL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $142 total per night from Aug 12 to Aug 13
$142 total
Aug 12 - Aug 13
Total includes taxes and fees
9.4/10 Exceptional! (937 reviews)
"Great location. Great staff.. Clean, modern spacious rooms."

Reviewed on Aug 6, 2025

Best Western Plus Winter Haven Inn & Suites 
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.

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Frequently asked questions

How much does a Winter Haven vacation package cost?
You'll find cheap prices from $550 on Expedia for your Winter Haven getaway. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Winter Haven costs.
What are the cheapest months to go to Winter Haven?
January, September and October are the best times to search for cheap Winter Haven vacation packages. Opting to travel in quieter months means you can usually find reduced prices on hotels and flights.
How many days is enough for Winter Haven?
Winter Haven vacations come in various shapes and sizes, but to get a true feel for this place, we reckon 2 days is about right. This will mean you can fit in headline attractions like Indigo's Billiards, Bowling & Games and Chain of Lakes Park and seek out some hidden gems. Don't skip cool neighborhoods such as Cypress Gardens and Inwood either. If you're clever with your time, you can even allow for a day trip from Winter Haven too.
Is it worth booking a vacation package to Winter Haven?
Popular for its golfing, hiking and views, a Winter Haven vacation is a hit with all types of travelers. Be sure to visit key sights like Chain of Lakes Park and Theatre Winter Haven, and consider renting a set of wheels for day trips to experience even more.
How to find the best Winter Haven package deals?
Use Expedia's filters to find some of the best Winter Haven package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Winter Haven package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Winter Haven vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging stays and flights individually. Better still, you can tailor your Winter Haven trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Winter Haven?
Score incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Winter Haven getaway.
How to plan a trip to Winter Haven?

  1. Choose when to go: Check your diary and get your bags packed. Your preferred season and the type of activities available will also help you decide when to escape to Winter Haven.
  2. Figure out your budget: Make sure you have enough money to pay for everything from food and transportation to activities and airfares. Your accommodations will likely be the largest expense during your trip to Winter Haven.
  3. Use Expedia's trip planning tool to discover Winter Haven: Research every aspect of your trip to Winter Haven with this handy planner. Invite family or friends to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Decide how many days away: Start by listing all the sights and activities you want to get to in Winter Haven. Then, estimate how long you'll need at each, including any travel time.
  5. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to pick a Winter Haven vacation package that brings all your bookings together.
  6. Book activities and experiences in advance: Whether it's entrance to a major attraction or a walking tour, you won't have to worry about missing out on the highlights of Winter Haven. Find all the exciting things to do in Winter Haven with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Winter Haven vacation packages?
If you're anything like us, you love traveling the world but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Winter Haven vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.