Webster Vacations from $269

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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 Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was $608, price is now $269 per person
$269
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,346 reviews)
Wonderful resort for families! The staff were incredibly helpful. Our representative, Tylah at the front desk pulled out a map and gave us options for room locations.

Reviewed on Sep 22, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $791, price is now $332 per person
$332
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (1,012 reviews)
Great place to stay close to Universal. Resort is quiet and has a laid back atmosphere. Pool and hot tub area great as well. Only negative I would have is restaurant closes way too early. I would recommend if looking for a great place to stay that is affordable.

Reviewed on Sep 20, 2025

Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was $795, price is now $369 per person
$369
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
8.4/10 Very Good! (1,001 reviews)
There was a very shady old looking red car parked outside our windows with loud music playing late into the night our last two nights

Reviewed on Aug 19, 2025

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $952, price is now $445 per person
$445
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (486 reviews)
Loved the pool and lazy rive and friendly staff at Tixi bar . Specially female bartender who made everyone feel at home . Thursday evening September 112025

Reviewed on Sep 15, 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was $947, price is now $479 per person
$479
per person
Dec 14 - Dec 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.6/10 Exceptional! (1,003 reviews)
Friendly staff at the front desk and in the hotel restaurant

Reviewed on Sep 23, 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
$107 nightly
The price is $120 total per night from Oct 1 to Oct 2
$120 total
Oct 1 - Oct 2
Total with taxes and fees
8.4/10 Very Good! (1,009 reviews)
Florida stay
"I stayed at this hotel many times when it was a Sleep Inn and enjoyed it. The hotel staff was very accommodating. I did not like the fact that I could not open my blinds to get some Florida sun. There was no curtain or anything to shield people from the outside looking in. I was on the first floor ..."

Reviewed on Sep 20, 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
$139 nightly
The price is $149 total per night from Sep 28 to Sep 29
$149 total
Sep 28 - Sep 29
Total with taxes and fees
9.6/10 Exceptional! (1,014 reviews)
"Nice hotel friendly staff."

Reviewed on Sep 18, 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
$85 nightly
The price is $91 total per night from Sep 28 to Sep 29
$91 total
Sep 28 - Sep 29
Total with taxes and fees
9.2/10 Wonderful! (1,011 reviews)
"Great customer service"

Reviewed on Sep 16, 2025

Holiday Inn Express & Suites Wildwood The Villages by IHG
See all 2,123 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 $269 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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