Webster Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
per person
Aug 26 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
7.8/10 Good! (1,649 reviews)
I liked everything about the property; however I did not get a balcony as it stated in my confirmation email and upon booking. I also did not like that the times available for the waterpark did not meet me needs at all, and it was closed as well as the pool whenever i wanted to go. I had a relative that stayed at the Westgate in Orlando, and their pool was open until 11pm and I enjoyed her balcony as I did not get one.

Reviewed on Jul. 22, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
per person
Sep 29 - Oct 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very Good! (5,097 reviews)
It has everything you’ll need for great family fun experience

Reviewed on Jul. 23, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
per person
Sep 27 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8.6/10 Excellent! (1,006 reviews)
A very clean and fragrant hotel. Close to all the parks and restaurants. The girl who works at the cafe is very friendly. I highly recommend it.

Reviewed on Jul. 22, 2025

ette hotel

ette hotel

5 out of 5
per person
Aug 26 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
9.8/10 Exceptional! (313 reviews)
Love our honeymoon stay

Reviewed on Jul. 23, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
per person
Aug 26 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8/10 Very Good! (1,277 reviews)
Great place to spend time on property and parks.

Reviewed on Jul. 25, 2025

Ready to book your vacation to Webster?

 

Choose your dates

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 $127 per night from Jul 29 to Jul 30
CA $127
CA $142 total
Jul 29 - Jul 30
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
"Great for what it is highly recommend."

Reviewed on Jul. 17, 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 $178 per night from Aug 17 to Aug 18
CA $178
CA $190 total
Aug 17 - Aug 18
includes taxes & fees
9.6/10 Exceptional! (1,015 reviews)
"This place is always great."

Reviewed on Jul. 23, 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 $133 per night from Aug 10 to Aug 11
CA $133
CA $143 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (1,013 reviews)
Would stay again!
"We traveled for a tournament for our son. So glad we booked here. The staff was so friendly and helpful. The breakfast was fantastic and they worked hard to keep hot fresh food coming. Thank you so much for your hospitality!!"

Reviewed on Jul. 25, 2025

Holiday Inn Express & Suites Wildwood The Villages by IHG
See all 2,064 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
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $707 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.