Webster Vacations from $365

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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.
  • A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.
    Jan 10 - Jan 16

    Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort + Flight

    Kissimmee
    6 nights
    2.0 star property
    9.0/10 - Wonderful (4,096 reviews)
    "Nice spot. To enjoy comfort peace and quiet. Coffee each morning was a bonus"
    Reviewed November 7, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $830
    $365
    per traveler
    found 1 day ago
    Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort
  • A resort with multiple buildings, a central pool area, a beach, and a dock with a boat.
    Jan 10 - Jan 16

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    6 nights
    4.0 star property
    9.2/10 - Wonderful (1,000 reviews)
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $1,704
    $781
    per traveler
    found 1 day ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark
  • A stone wall, a brown sofa with orange and yellow cushions, a glass table with a fire feature, and a wooden door with decorative glass panels.
    Jan 10 - Jan 16

    The Delaney Hotel + Flight

    South Orange
    6 nights
    3.5 star property
    9.6/10 - Exceptional (1,244 reviews)
    "Great Hotel. Well Located and the staff is very friendly!"
    Reviewed November 6, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $1,179
    $580
    per traveler
    found 1 day ago
    The Delaney Hotel
  • An outdoor pool area with red umbrellas, chairs, and a view of a body of water.
    Jan 10 - Jan 16

    Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive + Flight

    International Drive District
    6 nights
    3.0 star property
    7.8/10 - Good (636 reviews)
    "It was a newly remodeled property. Everything was real nice. Ran smooth. Would definitely stay there again."
    Reviewed November 6, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $848
    $441
    per traveler
    found 1 day ago
    Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
  • A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.
    Dec 11 - Dec 15

    Wyndham Grand Clearwater Beach + Flight

    Clearwater Beach
    4 nights
    4.0 star property
    9.4/10 - Exceptional (4,050 reviews)
    Roundtrip • Boston (BOS) - Tampa (TPA)
    BOS - TPA • Nonstop TPA - BOS • Nonstop
    $840
    $466
    per traveler
    found 2 days ago
    Wyndham Grand Clearwater Beach

Where to stay in and around Webster

Webster, Florida, offers a delightful blend of outdoor adventures and family-friendly experiences. Explore nearby attractions like Miami Beach for a taste of vibrant coastal life, while enjoying Webster's relaxing atmosphere and sunny weather. Perfect for outdoor enthusiasts and families alike, your vacation will be filled with fun and adventure.
An aerial view of a lakeside town with a dock extending into the water.

Clermont

For families and adventure seekers wanting a memorable trip, Clermont offers a vibrant mix of entertainment and outdoor experiences. You can explore the thrilling attractions of Walt Disney World® Resort, enjoy nature at Lake Louisa State Park, or tee off at Bella Collina Golf Club. Located about 18 miles by car from Webster, Clermont serves as an ideal base for your Florida getaway, making it a smart choice for hotel bookings.

A large, sprawling oak tree in a lush, green park.

Bushnell

Experience the charm of Bushnell, an excellent hub for families and nature enthusiasts eager to explore the great outdoors. This inviting city offers access to attractions like the Dade Battlefield State Park, perfect for a day of adventure, and the scenic Hog Island, ideal for relaxation. Just a short drive from Webster, Bushnell provides a budget-friendly option with plenty of recreational activities. Choosing Bushnell for your stay ensures a delightful base for your Florida getaway.

A sunset over a calm lake with a dock and a tree with Spanish moss.

Center Hill

If you are a family traveler or nature enthusiast, look no further than Center Hill, which features beautiful parks like Lake Harlow Canine Park and Venetian Gardens, perfect for outdoor fun. You can also explore the historic Dade Battlefield State Park, making for an enriching experience. Located about 5 miles from Webster, Center Hill offers a budget-friendly stay with access to shopping, golf, and nearby lakes. It's an ideal choice for those looking to enjoy a variety of activities.

Tarrytown

Tarrytown stands out as a prime spot for travelers interested in outdoor adventures and family getaways. Nestled in Webster, this charming village offers easy access to the scenic Withlacoochee Trail State Park, the wildlife experience at Giraffe Ranch, and the recreational opportunities at Lake David Park. With visitor numbers peaking during February to March and July, Tarrytown provides a welcoming atmosphere year-round. Choosing Tarrytown for your stay ensures a delightful blend of nature and leisure, making it a smart hotel booking choice.

Sumterville

Travelers visiting the area often choose Sumterville, especially families and nature enthusiasts seeking close proximity to outdoor adventures and city life. This charming city offers a delightful mix of activities, from exploring the vibrant Villages Market Square to enjoying the serene surroundings of Lake Okahumpka Park and the fun at Lake Harlow Canine Park. Located about 9 miles from Webster, Sumterville provides an ideal base for your adventures, making it a smart choice for your stay.

Discover the most popular places to visit in Webster

Webster Westside Flea Market

8.4/10 (40 reviews)
Florida's largest flea market spans 35 acres with 1,500 vendors selling antiques to fresh produce. Arrive early on Mondays for the best treasures and enjoy local food from the market's eateries.
See properties

Webster Hotel Deals

A hotel room with two beds, a TV, a desk, and a large window with curtains.

Microtel Inn & Suites by Wyndham Bushnell

Microtel Inn & Suites by Wyndham Bushnell
2.0 star property
6.9 mi from Webster
7.6 out of 10, Good, (1,004 reviews)
"I have stayed here before and left several reviews but if I don’t leave another Expedia will beat me up with emails so here is Another review, properly is a little outdated and needs some TLC, it is quite, comfy, and has cold a/c, nice bar and grill in the parking lot, it was great for the price, definitely recommend."
$82 nightly
The price is $88
Nov 10 - Nov 11
Total with taxes and fees
Microtel Inn & Suites by Wyndham Bushnell
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.
See all properties in Webster

Frequently Asked Questions

How much does a Webster vacation package cost?

You'll find cheap prices from $365 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.

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