Webster Vacations from $128

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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.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $539, price is now $128 per person
$128
per person
Feb 3 - Feb 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (5,210 reviews)
Room was clean and nice, pool was clean and well maintained. We were served for breakfast a scoop of powdered, watery eggs and 3 cold tater tots. Bread served were cheap dinner rolls. Coffee and liquid creamer were both watery and flavorless. We went out for a real breakfast for the rest of our stay.

Reviewed on Nov 9, 2025

Residence Inn by Marriott Daytona Beach Oceanfront

Residence Inn by Marriott Daytona Beach Oceanfront

3 out of 5
Price was $1,941, price is now $657 per person
$657
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
The only complaint I would have is the motorcycle parking fee. I wasn't told about the extra fee until I was checking in. I stay there a few times a year. Ive never had to pay an extra fee for parking. It's price gouging during bikeweek again.

Reviewed on Oct 24, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $1,288, price is now $448 per person
$448
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (1,037 reviews)
Great place and location

Reviewed on Nov 9, 2025

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $588, price is now $233 per person
$233
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (3,197 reviews)
Plain and simple, everything went great

Reviewed on Nov 10, 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was $1,325, price is now $552 per person
$552
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.6/10 Exceptional! (1,019 reviews)
Really nice and clean space in the middle of Orlando. Will stay here for future Orlando vacations.

Reviewed on Nov 3, 2025

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Discover the most popular places to visit in Webster

Webster Westside Flea Market

4/5(24 reviews)

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
$103 nightly
The price is $115 total per night from Nov 16 to Nov 17
$115 total
Nov 16 - Nov 17
Total with taxes and fees
8.4/10 Very Good! (1,005 reviews)
Plenty of shops nearby.

Reviewed on Nov 8, 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
$169 nightly
The price is $181 total per night from Nov 30 to Dec 1
$181 total
Nov 30 - Dec 1
Total with taxes and fees
9.6/10 Exceptional! (1,041 reviews)
All great !

Reviewed on Nov 7, 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 refundable
$103 nightly
The price is $110 total per night from Dec 7 to Dec 8
$110 total
Dec 7 - Dec 8
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
well lit parking, clean lot. front desk well staffed and courteous. breakfast service excellent

Reviewed on Nov 5, 2025

Holiday Inn Express & Suites Wildwood The Villages by IHG
See all 2,148 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 $128 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.