Webster Vacations from $252

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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 $609, price is now $252 per person
$252
per person
May 5 - May 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (5,482 reviews)
Was ok, dont recall expecting 30$ plus tax daily "resort" fee when booking. Also waterpark feature of the resort was closed for the season understandably due to chilly weather but that leads back to again, why resort fee?

Reviewed on Feb 8, 2026

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $1,248, price is now $305 per person
$305
per person
Apr 11 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (5,145 reviews)
What a blessing to be in such a lovely blessed and wholesome environment. It’s so awesome to have the beautiful music and scripture and words of affirmation on the walls. The rooms were spacious and clean and the room had a safe and a fridge. The hotel was well laid out. There was a children’s play room, and are stocked with ready made meals to purchase, a pool, and a beautiful outdoor area to relax around the lake. It wasn’t accessible to the public just walking through. There was a large complimentary breakfast in the breakfast room, which included cereals, porridge, toast and baked goods , waffles, a variety of cooked goods, some fruit, tea, coffee and fruit juice. There was also a laundry and a room with dining tables and microwave ovens. The staff were great. Would definitely stay there again

Reviewed on Feb 8, 2026

The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Save 100% on your flight
Price was $659, price is now $308 per person
$308
per person
Mar 23 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9/10 Wonderful! (1,681 reviews)
Everything was wonderful! I will stay again!

Reviewed on Feb 6, 2026

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $672, price is now $315 per person
$315
per person
Apr 14 - Apr 19
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Orlando (MCO)
8/10 Very Good! (1,703 reviews)
The room was spotless!

Reviewed on Feb 8, 2026

Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $636, price is now $302 per person
$302
per person
Mar 14 - Mar 19
found 1 hour ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
Clean and comfortable room

Reviewed on Feb 6, 2026

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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
$107 nightly
The price is $120 total per night from Feb 15 to Feb 16
$120 total
Feb 15 - Feb 16
Total with taxes and fees
8.2/10 Very Good! (1,005 reviews)
Clean rooms, front desk person was friendly and courteous along with attentive. The lady that prepared breakfast was also kind. Along with the housekeeper Erica was also friendly and kind. The whole staff works well together and will make your stay enjoyable. I am planning on returning.

Reviewed on Feb 4, 2026

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
$207 nightly
The price is $221 total per night from Mar 2 to Mar 3
$221 total
Mar 2 - Mar 3
Total with taxes and fees
9.6/10 Exceptional! (1,102 reviews)
I travel to The Villages every other month and I always stay at The Brownwood. From the minute I arrive, I feel pampered. The rooms are beautiful, the food from Wolfgang Puck is deicious, the pool and spa are delightful, and the service from staff members like Gabriella in the lively lobby lounge ...

Reviewed on Feb 5, 2026

Brownwood Hotel & Spa
Microtel Inn & Suites by Wyndham Leesburg/Mt Dora

Microtel Inn & Suites by Wyndham Leesburg/Mt Dora

2 out of 5
9700 Us Highway 441 Leesburg FL
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $96 total per night from Feb 23 to Feb 24
$96 total
Feb 23 - Feb 24
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
No issues

Reviewed on Feb 5, 2026

Microtel Inn & Suites by Wyndham Leesburg/Mt Dora
See all 2,189 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 $252 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.