Winter Haven Vacations from $288
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The Latest Winter Haven vacation packages
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$12,366
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Miami (MIA)
8/10 Very Good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
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Western Inn & Suites
2611 US-83 Carrizo Springs TX
Fully refundableReserve now, pay when you stay
$119 nightly
$134 total
Sep 17 - Sep 18
Total with taxes and fees
8.6/10 Excellent! (51 reviews)
"Stay was good my second time staying there and parking was great"
Reviewed on Aug 28, 2026
Texan Inn
2300 North 1st Street (Highway 83) Carrizo Springs TX
Fully refundableReserve now, pay when you stay
$114 nightly
$129 total
Sep 11 - Sep 12
Total with taxes and fees
7.2/10 Good! (109 reviews)
"Lady working the front desk was fantastic!"
Reviewed on Aug 13, 2026
Riata Inn Crystal City
1531 N Highway 83 Crystal City TX
Fully refundableReserve now, pay when you stay
$69 nightly
$78 total
Sep 10 - Sep 11
Total with taxes and fees
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.
Find the Best Winter Haven Vacation Packages
Winter Haven Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | Jefferson Park and Carrizo Springs Golf Course |
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Frequently asked questions
How much does a Winter Haven vacation package cost?
You'll find cheap prices from $288 on Expedia for your Winter Haven getaway. 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?
If you're hoping to book a cheap Winter Haven vacation package, consider traveling in February, November and December. You're likely to find better prices on hotels and flights during these months — perfect for a budget-friendly break.
How many days is enough for Winter Haven?
Typically, a handful of days is enough to explore the major sights during your Winter Haven vacation. But if you prefer to have some time to kick back or take day tours, consider extending your itinerary.
How to find the best Winter Haven package deals?
Landing a cheap Winter Haven package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, apply some filters and see what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most affordable Winter Haven package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Winter Haven vacation as a package?
You can enjoy significant savings on your Winter Haven escape by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to view the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Winter Haven?
If you've got your Winter Haven vacation dates finalized, book as soon as you can to snap up some incredible deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for quick escapes.
Does Expedia offer Book Now, Pay Later Winter Haven vacation packages?
Your Winter Haven break is meant to be an escape from your daily routine, not a reason for money worries. So to allow you extra flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
