Winter Haven Vacations from $563
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The Latest Winter Haven Vacation Packages
- ChartHouse Clearwater Beach Marina Hotel
Sep 8 - Sep 12ChartHouse Clearwater Beach Marina Hotel + Flight
Clearwater Beach4 nights2.0 star property9.6/10 - Exceptional (1,355 reviews)Roundtrip ā¢ Boston (BOS) - Tampa (TPA)BOS - TPA ā¢ Nonstop TPA - BOS ā¢ Nonstop - Cedar Cove Resort and Cottages
Oct 8 - Oct 14Cedar Cove Resort and Cottages + Flight
Holmes Beach6 nights3.0 star property9.2/10 - Wonderful (569 reviews)"Stayed for one night everything was in place very well thought off and cosy and very clean love the swing just out the door and seeing the shells all over and beach was amazing shower and beach chairs was in place staff was very friendly and had a home feeling I will be back"Reviewed August 5, 2026Roundtrip ā¢ Boston (BOS) - Tampa (TPA)BOS - TPA ā¢ Nonstop TPA - BOS ā¢ 1 stop - St Pete Beach Suites
Oct 10 - Oct 16St Pete Beach Suites + Flight
St. Pete Beach6 nights3.0 star property9.2/10 - Wonderful (1,003 reviews)Roundtrip ā¢ Boston (BOS) - Tampa (TPA)BOS - TPA ā¢ Nonstop TPA - BOS ā¢ Nonstop - Ocean Club Treasure Island Hotel
Oct 8 - Oct 14Ocean Club Treasure Island Hotel + Flight
Sunshine Beach6 nights4.0 star property9.6/10 - Exceptional (1,136 reviews)"This really is a nice and clean property, very well-maintained, they have so many staff members around and itās obvious they really care about the place! Great view of the beach and sunset from our very private balcony on the 6th floor! The room was well-stocked with everything we needed. I highly recommend this place and would come back!"Reviewed August 4, 2026Roundtrip ā¢ Boston (BOS) - Tampa (TPA)BOS - TPA ā¢ Nonstop TPA - BOS ā¢ 1 stop - CW Hotel
Sep 8 - Sep 12CW Hotel + Flight
Clearwater Beach4 nights4.0 star property9.6/10 - Exceptional (56 reviews)"Amazing views and beautiful pool. Food was delicious! Definitely will be back."Reviewed August 6, 2026Roundtrip ā¢ Boston (BOS) - Tampa (TPA)BOS - TPA ā¢ Nonstop TPA - BOS ā¢ Nonstop
Where to stay in Winter Haven
Florence Villa
If you're looking for some top things to see and do in Florence Villa and surrounding area, you can visit Winter Haven City Tennis Center and Winter Haven Public Library.
Lucerne Park
Lucerne Park might not have many top sights, but Lake Henry Golf Club and Willowbrook Golf Course are two attractions nearby that you can check out.
Discover the most popular places to visit in Winter Haven
What to do in Winter Haven
LEGOLAND Florida FasTrack Pass
Winter Haven Hotel Deals
Holiday Inn Winter Haven by IHG
Holiday Inn Winter Haven by IHG"My bed had bedbugs, and I was bitten badly during my stay. This is the first time I've ever experienced something like this at any hotel. I am extremely disappointed and would not recommend staying here."
Best Western Plus Winter Haven Inn & SuitesĀ
Best Western Plus Winter Haven Inn & SuitesĀ"All was good, clean, friendly staff and good breakfast"
Staybridge Suites Winter Haven Auburndale by IHG
Staybridge Suites Winter Haven Auburndale by IHG"Staff was very nice to me"
Howard Johnson by Wyndham Winter Haven FL
Howard Johnson by Wyndham Winter Haven FL"Great place to stay, but breakfast is limited to only a handful of items."
Courtyard by Marriott Winter Haven
Courtyard by Marriott Winter Haven"Very nice property"
"We were disappointed with our stay. The cabin had a musty smell from the moment we entered, and after two nights it caused nasal irritation. The entire property felt very dated. The air conditioner, cabinets, and bathroom all seemed old, and the mirror in the bathroom showed visible wear. The lighting was also very dim, making the room feel dark. If this is the intended style, it still did not provide a comfortable experience for us. We also found the outdoor playground to be quite...
Home2 Suites By Hilton Winter Haven
Home2 Suites By Hilton Winter Haven"Everything perfect"
Frequently Asked Questions
How much does a Winter Haven vacation package cost?
You'll find cheap prices from $563 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?
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
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Things to do in and around Winter Haven
Winter Haven is perfect for family-friendly adventures, offering a variety of activities such as exciting amusement parks, a thrilling water park, and beautiful resort accommodations. Visitors can enjoy beach vacations, themed attractions, and festive holiday events, making it an ideal destination for fun and relaxation. Don't miss the chance to experience the vibrant shopping areas and exhilarating rides that Winter Haven has to offer.
Shopping
The nearest shopping spot is Northgate Shopping Center, offering a lively mix of entertainment and family-friendly options. Havendale Plaza Shopping Center, located 7 miles away, features similar vibes. If you're up for a drive, check out Eagle Ridge Mall, 9 miles from Winter Haven, for a broader selection.
Recreation
Chain of Lakes Park offers a vibrant atmosphere for sports enthusiasts, perfect for jogging or a leisurely walk. Theatre Winter Haven immerses visitors in culture with its engaging performances, ideal for family outings. For golf lovers, Lake Henry Golf Club provides a scenic outdoor experience on its well-maintained greens.
Adventure
Experience the thrill of gaming at Indigo's Billiards, Bowling & Games, perfect for family fun. Hike the scenic Fort Fraser Trail, surrounded by nature's beauty, or take to the skies with Jump Florida Skydiving for an exhilarating aerial adventure, both located a short drive from Winter Haven.
Nightlife
Winter Haven's nightlife offers a unique blend of fun and romance at Indigo's Family Fun Center. Enjoy a vibrant atmosphere with drinks and entertainment, making it the perfect spot to unwind and socialize after a long day of exploring. Experience the local charm and vibrant energy of this lively pub.
Find the best attractions in and around Winter Haven
Winter Haven, Florida, is an ideal destination for family-friendly outdoor adventures. With its stunning lakes, exciting amusement parks, and beautiful urban parks, visitors can enjoy a variety of activities that cater to both adventure seekers and those looking for a relaxing beach experience. Whether you're exploring nature or having fun at local attractions, Winter Haven promises memorable experiences for travelers of all ages.
- LEGOLANDĀ® Florida: Dive into a world of creativity and imagination at LEGOLANDĀ® Florida, where families can enjoy thrilling rides, interactive attractions, and stunning LEGO-themed displays. Perfect for kids and the young at heart, this amusement park promises a day full of adventure and fun.
- Auburndale City Park: Just 5 miles from Winter Haven, Auburndale City Park offers a serene escape with lush green spaces, playgrounds, and picnic areas. It's an ideal spot for families seeking outdoor activities, walking trails, and a taste of city life in a relaxing environment.
- The Circle B Bar Reserve: Located 9 miles from Winter Haven, this nature preserve invites you to explore its scenic trails and diverse wildlife. Ideal for adventure enthusiasts, it offers opportunities for hiking, birdwatching, and connecting with Florida's natural beauty.
Best time to go to Winter Haven
The best time to visit Winter Haven is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with moderate rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.
Tips to save on your trip to Winter Haven
- Combine your flights, hotels and car rentals on Expediaābundling can result in significant savings.
- Consider traveling to Winter Haven during the low season (August to September and November) for more affordable options.
- Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
- Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.