Webster Vacation Packages

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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.

Top Webster Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Davis
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Orlando (MCO)
8.4/10 Very Good! (1,404 reviews)
I enjoy every thing about the property was great

Reviewed on Aug. 10, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
per person
Sep 23 - Sep 30
found 20 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Orlando (MCO)
8.8/10 Excellent! (1,013 reviews)
Very clean and beds were comfortable. However the rooms felt cold and sterile with no decore’ or anything to make it feel warm and inviting. Also very noisy as there are no drapes or rugs or anything to dampen the sounds. Also, transportation is only for Universal. The description says free shuttle to “parks” which is misleading. Disappointed in the “grille” as it was only open 1 day and we were there for an entire week. If your looking for a place to just crash at night then It’s fine. If your wanting more of a resort then maybe look elsewhere.

Reviewed on Aug. 11, 2025

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Orlando (MCO)
8/10 Very Good! (1,670 reviews)
It's a good place, I would just add that they need more tables and seats in the water park area, which is where everyone wants to be during the day.

Reviewed on Aug. 9, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
per person
Sep 13 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (574 reviews)
As a travel agent I have traveled extensively and reviewed a plethora of properties. I would highly recommend Ocean Club. The check in area is small but it gets the job done. All condos are gulf front with beautiful views. Previous reviews remarked about the music from the pool- we were in room 206 which is almost directly above the pool and we didn’t have a problem. The actual Condo is very clean with everything you need for your stay- pots and pans, dishes, can opener, toaster, keurig (complete with a variety of pods), quality towels, and comfortable beds. There is also a full size washer and dryer in each unit. Others also remarked about “the trek” to the beach. Please remember that the waterline on a beach is variable and building codes require structures to be specific distances from the beach. Additionally, Florida law prohibits the destruction of certain grasses and sea oats. You can rent chairs and umbrellas on the beach OR there are plenty of umbrellas, chairs, sand toys,and floats that are in a communal area left by previous guests. There is a limit to one car per unit and with this parking is free. WiFi can be spotty as my partner did have to use her hotspot in order to work from our unit.

Reviewed on Aug. 12, 2025

The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Orlando (MCO)
9/10 Wonderful! (1,703 reviews)
I have 2 teen age daughters I appreciated the security of the property going to and from the beach.

Reviewed on Aug. 11, 2025

Ready to book your vacation to Webster?

 

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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
The price is CA $135 per night from Aug 17 to Aug 18
CA $135
CA $151 total
Aug 17 - Aug 18
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
"Great customer service by David, Mariana and kitchen staff. Tasty breakfast."

Reviewed on Aug. 4, 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
The price is CA $166 per night from Sep 7 to Sep 8
CA $166
CA $178 total
Sep 7 - Sep 8
includes taxes & fees
9.6/10 Exceptional! (1,005 reviews)
"Great stay. Pool area was beautiful. Excellent staff. Beds were very comfortable and the sheets are so soft"

Reviewed on Aug. 9, 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
The price is CA $128 per night from Sep 1 to Sep 2
CA $128
CA $137 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"I really loved this hotel. I will be returning whenever I’m in the area."

Reviewed on Aug. 10, 2025

Holiday Inn Express & Suites Wildwood The Villages by IHG
See all 2,078 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.
All Inclusive Vacations
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Beach Vacations
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Family Vacations
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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

Frequently asked questions

How much does a Webster vacation package cost?
You'll find cheap prices from CA $553 on Expedia for your Webster getaway. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Webster costs.
What are the cheapest months to go to Webster?
January, February and June are the best times to search for cheap Webster vacation packages. Opting to travel in quieter months means you can generally find lower prices on accommodations and flights.
How many days is enough for Webster?
With a well-organized travel plan, you can easily hit the most popular Webster attractions in a handful of days. But if you'd like to discover hidden gems or go on day trips, think about booking your Webster vacation for longer.
How to find the best Webster package deals?
Finding a cheap Webster package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a few filters and see what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Webster package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Webster vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and stays individually. Better still, you can tailor your Webster trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Webster?
If you've got your Webster vacation dates finalized, book early to score some fantastic deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to Webster?

  1. Choose your dates: What you plan to do in Webster and your favourite season will help you decide when to travel.
  2. Calculate your budget: Make sure you have enough money to pay for everything from food and transportation to flights and activities. Your hotel will likely be the biggest expense during your trip to Webster.
  3. Decide your trip length: Think about how much time you'd like to spend exploring Webster. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Combine your airfare and accommodations: Once you've nailed down your trip dates and duration, book the perfect Webster vacation package for you.

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