Webster Vacations from $314

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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 $1,143, price is now $314 per person
$314
per person
Feb 24 - Mar 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (5,145 reviews)
The room is very nice and the staff was very courteous. The AC was not working well and the vending machines were all out of order .. those were my only issues. Also if you want to enjoy the breakfast go really early. It’s really busy after 8am.

Reviewed on Dec 23, 2025

Residence Inn by Marriott Daytona Beach Oceanfront

Residence Inn by Marriott Daytona Beach Oceanfront

3 out of 5
Price was $2,728, price is now $1,100 per person
$1,100
per person
Feb 26 - Mar 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
The outside of the building could use some tlc but inside was clean and updated. Staff was attentive, polite, & helpful. Breakfast was surprisingly better than I anticipated with hot options outside of the traditional continental options. Furniture around pool was pressure washed every morning and plentiful. There are no seating options for the beach however we would definitely stay here again.

Reviewed on Nov 30, 2025

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $2,098, price is now $903 per person
$903
per person
Mar 10 - Mar 14
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
8.8/10 Excellent! (500 reviews)
Everything was great! Staff were super!!

Reviewed on Dec 22, 2025

Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Price was $1,371, price is now $621 per person
$621
per person
Mar 13 - Mar 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
No reviews
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $772, price is now $354 per person
$354
per person
Feb 24 - Mar 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8/10 Very Good! (1,367 reviews)
La habitacion muy buena y limpia expaciosa recomendaria cambiar ollas y sartenes estan muy viejos y quemados

Reviewed on Dec 4, 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
$98 nightly
The price is $110 total per night from Jan 4 to Jan 5
$110 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
staff is amazing. Accommodating with my request for a different room on a higher floor without thinking twice. Room was clean. Consistency with my stay compared to last visit

Reviewed on Dec 19, 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
$136 nightly
The price is $145 total per night from Jan 1 to Jan 2
$145 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
9.6/10 Exceptional! (1,069 reviews)
Room was very clean and bed was exceptionally comfortable. Housecleaning service was performed mid-morning every day and was spotless. The one issue that prevented a 5 star is the hotel host events and staying guests do not have reserved parking. This require guest to find parking

Reviewed on Dec 19, 2025

Brownwood Hotel & Spa
Days Inn by Wyndham Brooksville/Dade City

Days Inn by Wyndham Brooksville/Dade City

2 out of 5
6320 Windmere Rd Brooksville FL
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $83 total per night from Dec 28 to Dec 29
$83 total
Dec 28 - Dec 29
Total with taxes and fees
7/10 Good! (1,000 reviews)
The room was very clean, and the staff was very friendly, especially the gentleman at the front desk. I asked for a bottom floor room and he graciously accommodated and I’m forever grateful for that. It’s the little thing sometimes!

Reviewed on Dec 21, 2025

Days Inn by Wyndham Brooksville/Dade City
See all 2,168 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 $314 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.