Webster Vacations from $274

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Your Webster Vacation

Come and discover this wonderful city for yourself with a Webster vacation package. Consider basing yourself in the neighborhood of Tarrytown, which is great for camping and families, and your time here will be nothing short of unforgettable. Need some sightseeing ideas for your trip to Webster? Webster Westside Flea Market and Dade Battlefield State Park are two of the main attractions here. A few clicks is all it takes to create your perfect Webster vacation on Expedia.

The Latest Webster vacation packages

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (2,970 reviews)
Good place to take a shower and sleep in a cool room

Reviewed on Jul 30, 2025

Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
per person
Oct 14 - Oct 20
found 2 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.6/10 Excellent! (1,003 reviews)
This place is very family and pet friendly,

Reviewed on Jul 28, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,097 reviews)
Overall good experience. The villas need to be updated, more modern. The staff was helpful.

Reviewed on Jul 30, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.6/10 Excellent! (1,006 reviews)
I arrived with my family at Westgate and the check in process was easy. Staff helpful and friendly. The room was comfortable and clean. Loved the place. Very near the Universal parks. Will stay again.

Reviewed on Jul 31, 2025

ette hotel

ette hotel

5 out of 5
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.8/10 Exceptional! (313 reviews)
Fantastic hotel. Beautiful room, great food, exceptional staff and the smell was phenomenal

Reviewed on Jul 27, 2025

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Discover the most popular places to visit in Webster

Webster Westside Flea Market

You can do some window-shopping at Webster Westside Flea Market during your trip to Webster. You can enjoy the coffeehouses while in the area.

Webster Westside Flea Market

Webster Hotel Deals

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
$93 nightly
The price is $104 total per night from Aug 4 to Aug 5
$104 total
Aug 4 - Aug 5
Total includes taxes and fees
8.4/10 Very Good! (1,013 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 Jul 27, 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
$154 nightly
The price is $165 total per night from Aug 17 to Aug 18
$165 total
Aug 17 - Aug 18
Total includes taxes and fees
9.6/10 Exceptional! (1,029 reviews)
"Loved the place and very convenient to everything at the Brownwood Town Sq"

Reviewed on Jul 28, 2025

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
$97 nightly
The price is $104 total per night from Aug 10 to Aug 11
$104 total
Aug 10 - Aug 11
Total includes taxes and fees
9.2/10 Wonderful! (1,000 reviews)
"Everything was great"

Reviewed on Jul 30, 2025

Holiday Inn Express & Suites Wildwood The Villages by IHG
See all 2,064 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.

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Frequently asked questions

How much does a Webster vacation package cost?
You'll find cheap prices from $274 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 vacation to Webster costs.
What are the cheapest months to go to Webster?
You can typically find reduced prices and greater availability in June, July and October. Browse our cheap Webster vacation packages and you could get some great off-season deals.
How many days is enough for Webster?
Usually, a handful of days is enough to go to the major attractions during your Webster vacation. But if you'd like to have more time to chill out or take day tours, consider extending your itinerary.
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 vacation as a package?
Expedia vacation 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 personalized Webster vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation 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.
Does Expedia offer Book Now, Pay Later Webster vacation packages?
If you're like us, you love traveling the world but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Webster vacation across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.