Webster Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Webster

SPOT X Hotel Tampa - Wesley Chapel by The Red Collection

SPOT X Hotel Tampa - Wesley Chapel by The Red Collection

3 out of 5
5703 Oakley Blvd, Wesley Chapel, FL
Fully refundableReserve now, pay when you stay
The price is S$129 per night from 7 Aug to 8 Aug
S$129
7 Aug - 8 Aug
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"The stay at Spot X is highly recommended staycation. And for the location to be around restaurants, Publix Walmart and now a new target being build just across the street and to be a walking distance from the Krates. Our front desk check in is kind and beautiful. Staff is very direct and helpful ..."

Reviewed on 27 Jul, 2025

SPOT X Hotel Tampa - Wesley Chapel by The Red Collection
Brownwood Hotel & Spa

Brownwood Hotel & Spa

3 out of 5
3003 Brownwood Blvd, Wildwood, FL
Fully refundableReserve now, pay when you stay
9.6/10 Exceptional! (1,003 reviews)
"My kids love the pool!! Staff super nice and the facilities very clean!! Will stay again,definitely a 10 out of 10 star rating!!"

Reviewed on 1 Aug, 2025

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Brownwood Hotel & Spa
Holiday Inn Express & Suites Wildwood The Villages by IHG

Holiday Inn Express & Suites Wildwood The Villages by IHG

3.5 out of 5
928 East State Road 44, Wildwood, FL
Fully refundableReserve now, pay when you stay
The price is S$128 per night from 1 Sept to 2 Sept
S$128
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"Absolutely loved it, very clean, very big room. Bathroom was very clean. Big fridge. Pool was nice and the breakfast was wonderful a lot to choose from"

Reviewed on 2 Aug, 2025

Holiday Inn Express & Suites Wildwood The Villages by IHG
See all 2,074 properties in Webster
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 Webster holiday package cost?
You'll find cheap prices on Expedia for your Webster escape. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your holiday to Webster costs.
What are the cheapest months to go to Webster?
If you're looking to snag a cheap Webster holiday package, consider travelling in January, February and June. You'll typically find better rates on hotels and flights during these months — perfect for a budget-friendly break.
How many days is enough for Webster?
Generally, a handful of days is enough to check out the major attractions during your Webster holiday. But if you prefer to have more time to relax or go on day tours, consider extending your trip.
How to find the best Webster package deals?
Begin your search for a Webster package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Webster package deal right away, just play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Webster getaway off to a flying start.
Is it cheaper to book a Webster holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalised Webster holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Webster?
If you've got your Webster travel dates confirmed, book as soon as you can to grab some unbeatable deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Webster?

  1. Pick your travel dates: What you plan to do in Webster and your favourite season will help you decide when to go.
  2. Set a budget: Consider expenses like food, flights and transportation when working out how much to save for your trip to Webster. Then, pick a property that matches your budget, whether that's an affordable option or a high-end retreat.
  3. Decide how long to go for: Now that you're more familiar with Webster, you can work out the perfect length of your break. Pull together a rough itinerary and allocate enough time for all the things you want to do.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to find a Webster holiday 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. 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.