Winter Haven Holidays

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  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Winter Haven Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
YOTEL New York Times Square

YOTEL New York Times Square

4 out of 5
Manhattan
Price was S$4,151, price is now S$3,303 per person
S$3,303
per person
15 Dec - 22 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to New York (JFK)
7.8/10 Good! (3,136 reviews)

Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Manhattan
Price was S$4,885, price is now S$3,579 per person
S$3,579
per person
15 Dec - 22 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to New York (JFK)
8.4/10 Very good! (1,813 reviews)

Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Price was S$5,457, price is now S$4,051 per person
S$4,051
per person
15 Dec - 22 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9/10 Wonderful! (4,191 reviews)

Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
Price was S$4,615, price is now S$3,654 per person
S$3,654
per person
15 Dec - 22 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to New York (JFK)
8.6/10 Excellent! (2,296 reviews)

Hilton Garden Inn New York/Manhattan-Chelsea

Hilton Garden Inn New York/Manhattan-Chelsea

3 out of 5
Manhattan
Price was S$4,723, price is now S$3,771 per person
S$3,771
per person
15 Dec - 22 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to New York (JFK)
8/10 Very good! (3,180 reviews)

Top hotels in Winter Haven

Western Inn & Suites

Western Inn & Suites

2.5 out of 5
2611 US-83 Carrizo Springs TX
Fully refundableReserve now, pay when you stay
The price is S$182 per night from 6 Nov to 7 Nov
S$182
6 Nov - 7 Nov
includes taxes & fees
Western Inn & Suites
EL Dorado ranch resort

EL Dorado ranch resort

2.5 out of 5
5150 Farm to Market 191 Crystal City TX
Fully refundableReserve now, pay when you stay
The price is S$135 per night from 6 Nov to 7 Nov
S$135
6 Nov - 7 Nov
includes taxes & fees
EL Dorado ranch resort
Wintergarden Inn

Wintergarden Inn

2.5 out of 5
2516 N Highway 83 Crystal City TX
Fully refundable
The price is S$90 per night from 6 Nov to 7 Nov
S$90
6 Nov - 7 Nov
includes taxes & fees
6.6/10 (104 reviews)
"I made a reservation a got there late and my room was no longer available. No notification so can look elsewhere. Had to drive back home."

Reviewed on 1 Nov, 2026

Wintergarden Inn
See all 27 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 from S$3,303 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 holiday to Winter Haven costs.
What are the cheapest months to go to Winter Haven?
If you're looking to snag a cheap Winter Haven holiday package, consider visiting in January, February and May. You'll usually find lower prices on flights and accommodation during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Winter Haven?
Generally, a handful of days is enough to visit the top attractions during your Winter Haven holiday. But if you prefer to have time to kick back or go on day trips, 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 personalise 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 holiday as a package?
You can enjoy significant savings on your Winter Haven escape by booking a personalised holiday package. Check the "Package" heading, then select your destination and travel dates to view the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Winter Haven?
If you've got your Winter Haven holiday 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.
How to plan a trip to Winter Haven?

  1. Choose your dates: The things you'd like to do in Winter Haven and your preferred season will help you decide when to get away.
  2. Set a budget: Factor in costs such as flights, food and transportation when working out how much to set aside for your trip to Winter Haven. Then, pick a property that matches your budget, whether that's an economical option or a high-end retreat.
  3. Determine how many days away: Start by listing all the attractions and activities you'd like to experience in Winter Haven. Then, estimate how long you'll need for each, as well as any travel time.
  4. Combine your airfare and accommodation: Once you've settled on your dates and duration, lock in the perfect Winter Haven holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.