Winter Haven Trip

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to ₹43,962 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Winter Haven

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
The price is ₹11,692 per night from 4 May to 5 May
₹11,692
₹13,096 total
includes taxes & fees
4 May - 5 May
9.4/10 Exceptional! (778 reviews)
"Staff was very friendly."

Reviewed on 16 Apr 2025

Best Western Plus Winter Haven Inn & Suites 
Home2 Suites By Hilton Winter Haven
Home2 Suites By Hilton Winter Haven
3 out of 5
6015 Cypress Gardens Blvd, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is ₹10,813 per night from 4 May to 5 May
₹10,813
₹12,111 total
includes taxes & fees
4 May - 5 May
9/10 Wonderful! (77 reviews)
See above
"The hotel room were very nice and spacious with everything you need. It was great that we could walk to Peppa Pig and Legoland."

Reviewed on 18 Apr 2025

Home2 Suites By Hilton Winter Haven
Howard Johnson by Wyndham Winter Haven FL
Howard Johnson by Wyndham Winter Haven FL
2 out of 5
1300 3rd St, SW, Winter Haven, FL
Fully refundableReserve now, pay when you stay
The price is ₹8,709 per night from 23 Apr to 24 Apr
₹8,709
₹9,754 total
includes taxes & fees
23 Apr - 24 Apr
6.8/10 (1,001 reviews)
"The rooms are very clean, nice rooms. Bed are ok,"

Reviewed on 6 Apr 2025

Howard Johnson by Wyndham Winter Haven FL
See all 37,886 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.

Frequently asked questions

How much does a Winter Haven holiday package cost?
You’ll find cheap prices on Expedia for your Winter Haven getaway. However, factors like the hotel choice, length of stay and season will determine how much your holiday to Winter Haven costs.
What are the cheapest months to go to Winter Haven?
You can generally find reduced prices and better availability in September, October and November. Explore our cheap Winter Haven holiday packages and you could get some great off-season discounts.
How many days is enough for Winter Haven?
Dedicate around 2 days for your Winter Haven holiday if you’re hoping to enjoy everything that makes this place unique. Stroll around popular neighbourhoods, including Cypress Gardens and Jan Phyl Village. Then tick off top attractions like Indigo’s Billiards, Bowling & Games and Indigo’s Family Fun Centre. With a good itinerary, you’ll be kept busy with room for some downtime too. Want to travel outside of Winter Haven? Consider fitting in a day trip or two.
Is it worth booking a holiday package to Winter Haven?
Popular for its fishing, walking trails and golfing, a Winter Haven holiday is a hit with all kinds of visitors. Be sure to check out top sights like Chain of Lakes Park and Theatre Winter Haven, and consider renting a set of wheels for day trips to explore 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 holiday package well in advance.
Is it cheaper to book a Winter Haven holiday as a package?
An Expedia holiday 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 holiday 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 the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Winter Haven.
  2. Set your budget: Consider costs such as food, flights and transportation when calculating how much to save for your trip to Winter Haven. Then, pick a hotel that matches your budget, whether that’s an affordable option or a lavish retreat.
  3. Determine how many days away: Start by compiling a list of the activities and attractions you want to experience in Winter Haven. Then, estimate how long you’ll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a customised Winter Haven holiday package.

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