Webster Vacations from $195

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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.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $403, price is now $195 per person
$195
per person
Mar 1 - Mar 4
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (1,367 reviews)
Room was very spacious and clean upon arrival. Was able to checkin a hr early and the resort has very many amenities. The mexican restaurants brunch was 5 stars. Will definitely be back!

Reviewed on Jan 25, 2026

Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Price was $1,267, price is now $490 per person
$490
per person
Apr 6 - Apr 11
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
Courteous staff and clean room.

Reviewed on Jan 25, 2026

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $1,931, price is now $883 per person
$883
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (500 reviews)
Clean rooms, nice staff, good amenities!

Reviewed on Jan 25, 2026

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $501, price is now $252 per person
$252
per person
Mar 20 - Mar 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (1,703 reviews)
Everything was good

Reviewed on Jan 24, 2026

The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Save 100% on your flight
Price was $502, price is now $267 per person
$267
per person
Mar 11 - Mar 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9/10 Wonderful! (1,681 reviews)
Great location, way over prived parking and heart daily resort fee added to end of stay. Ended up being an extra $250 for 3 nights that we didn’t expect. Some staff was friendly, others were cranky.

Reviewed on Jan 24, 2026

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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

Brownwood Hotel & Spa

Brownwood Hotel & Spa

3 out of 5
3003 Brownwood Blvd Wildwood FL
Fully refundableReserve now, pay when you stay
$163 nightly
The price is $174 total per night from Jan 29 to Jan 30
$174 total
Jan 29 - Jan 30
Total with taxes and fees
9.6/10 Exceptional! (1,086 reviews)
A

Reviewed on Jan 22, 2026

Brownwood Hotel & Spa
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
$109 nightly
The price is $122 total per night from Jan 28 to Jan 29
$122 total
Jan 28 - Jan 29
Total with taxes and fees
8.2/10 Very Good! (1,013 reviews)
All very good

Reviewed on Jan 24, 2026

SPOT X Hotel Tampa - Wesley Chapel by The Red Collection
Roadstar Hotel Zephyrhills

Roadstar Hotel Zephyrhills

2 out of 5
5734 Gall Blvd Zephyrhills FL
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $114 total per night from Jan 28 to Jan 29
$114 total
Jan 28 - Jan 29
Total with taxes and fees
9/10 Wonderful! (1,126 reviews)
Staff very courteous and room was clean. Grounds were well maintained.

Reviewed on Jan 22, 2026

Roadstar Hotel Zephyrhills
See all 2,181 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.

Find the Best Webster Vacation Packages

Webster Essential Information

Language
English
Currency
U.S dollars
Population
1,000
Top Sights
Dade Battlefield State Park, The Florida International Teaching Zoo and Webster Westside Flea Market

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Frequently asked questions

How much does a Webster vacation package cost?
You'll find cheap prices from $195 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.