Winter Haven Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Ready to book your vacation to Winter Haven?
Winter Haven Hotel Deals
Holiday Inn Winter Haven by IHG
200 Cypress Gardens Boulevard Winter Haven FL
Fully refundable
CA $145
CA $163 total
Sep 20 - Sep 21
includes taxes & fees
9/10 Wonderful! (1,019 reviews)
"Clean, free wifi, great location, overall good experience with family."
Reviewed on Sep 8, 2026
Best Western Plus Winter Haven Inn & Suites
5801 Roosevelt Dr Winter Haven FL
Fully refundableReserve now, pay when you stay
CA $169
CA $189 total
Sep 15 - Sep 16
includes taxes & fees
9.6/10 Exceptional! (1,374 reviews)
"My first time in this hotel. Honestly I give it a 10/10 Love it"
Reviewed on Sep 9, 2026
Staybridge Suites Winter Haven Auburndale by IHG
305 5th St NW and Avenue D NW Winter Haven FL
Fully refundable
CA $162
CA $181 total
Sep 13 - Sep 14
includes taxes & fees
9.8/10 Exceptional! (901 reviews)
"The room was amazing and spacious. We had just moved to the area and had a few days before closing on our new home. I was able to work comfortably without feeling uncomfortable. The wi-fi was perfect, the staff amazing and again, the room was so big. It had everything we needed for our stay in the ..."
Reviewed on Sep 11, 2026
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.
Stay near popular Winter Haven attractions
LEGOLAND® Florida
9.0/10 (2,150 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.
Chain of Lakes Park
8.2/10 (185 reviews)
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.
Peppa Pig Theme Park Florida
Have a fun-filled day with the family at Peppa Pig Theme Park Florida during your visit to Winter Haven. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.
Theatre Winter Haven
7.4/10 (56 reviews)
You can enjoy a show at Theatre Winter Haven during your trip to Winter Haven. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
Cypresswood Golf and Country Club
6.4/10 (25 reviews)
Enjoy a round of golf in Winter Haven at Cypresswood Golf and Country Club. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
Inman Park
7.4/10 (14 reviews)
Inman Park is just one of the places to see in Winter Haven, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
Willowbrook Golf Course
6.8/10 (15 reviews)
Enjoy a round of golf in Winter Haven at Willowbrook Golf Course. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.
Lake Henry Golf Club
6.0/10 (11 reviews)
Enjoy a round of golf in Winter Haven at Lake Henry Golf Club. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.
What to do in Winter Haven
Ladies Luncheon Pontoon Tour (Gentleman welcome)
CA $138
per adult
Frequently asked questions
How much does a Winter Haven vacation package cost?
You'll find cheap prices from CA $820 on Expedia for your Winter Haven escape. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Winter Haven costs.
What are the cheapest months to go to Winter Haven?
You can typically find lower rates and greater availability in September, October and November. Check out our cheap Winter Haven vacation 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 vacation to really discover all that makes this place special. Explore popular areas, including Cypress Gardens and Jan Phyl Village. Then make a beeline for top attractions like Auburndale City Park and Theatre Winter Haven. With a good itinerary, you'll be kept busy with room for some downtime too. Want to venture outside of Winter Haven? Consider fitting in an excursion or two.
Is it worth booking a vacation package to Winter Haven?
Whether you're looking to visit top attractions like Chain of Lakes Park and Theatre Winter Haven on your Winter Haven vacation, or coming for its great fishing, walking trails and golfing, there's something for everyone here. With so much to do, you'll soon find out why so many visitors think Winter Haven is a good vacation destination.
How to find the best Winter Haven package deals?
Start your search for a Winter Haven package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Winter Haven package deal straight away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Winter Haven adventure off to a flying start.
Is it cheaper to book a Winter Haven vacation as a package?
You can enjoy significant savings on your next Winter Haven break by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Winter Haven?
Secure incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Winter Haven getaway.
How to plan a trip to Winter Haven?
- Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Winter Haven.
- Work out your budget: Ensure you have enough money to cover everything from dining out and transportation to activities and flights. Your accommodations will probably be the largest expense during your trip to Winter Haven.
- Set the duration of your trip: Start by listing all the attractions and activities you want to experience in Winter Haven. Then, estimate how long you'll need at each, including any travel time.
- Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Winter Haven vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
