Deals on vacations and trips to Webster

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Webster flight + hotel vacation packages

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Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $691, price is now $300 per person
$300
per person
Mar 26 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
This smoke-free resort features a water park, a marina, and 2 restaurants. There's fun for all ages with a children's club and mini golf, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and perks like free self parking and free WiFi.
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $2,339, price is now $1,072 per person
$1,072
per person
Feb 22 - Feb 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Free water park access and an outdoor pool are featured at this smoke-free condo resort. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. There's fun for all ages with a lazy river and a children's pool, and barbecue grills are available on site.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Save 100% on your flight
Price was $664, price is now $304 per person
$304
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
This smoke-free resort features a water park, a marina, and 2 restaurants. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and get free self parking.
Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Price was $1,442, price is now $729 per person
$729
per person
Mar 16 - Mar 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Free water park access, 4 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas. You'll appreciate the hot tub, poolside bar, and snack bar/deli.
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $728, price is now $376 per person
$376
per person
Mar 26 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
This smoke-free hotel features a full-service spa, a water park, and a marina. There's fun for all ages with a lazy river and a children's club, and barbecue grills are available on site. Enjoy the 7 outdoor pools and perks like free valet parking and a free theme park shuttle.

Top Webster hotels 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
Free Cancellation
Reserve now, pay when you stay
$98 nightly
The price is $110 total per night
$110 total
Jan 19 - Jan 20
Total with taxes and fees
This hotel features an outdoor pool and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Brownwood Hotel & Spa

Brownwood Hotel & Spa

3 out of 5
3003 Brownwood Blvd Wildwood FL
Free Cancellation
Reserve now, pay when you stay
$156 nightly
The price is $167 total per night
$167 total
Jan 14 - Jan 15
Total with taxes and fees
A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Spa
Days Inn by Wyndham Brooksville/Dade City

Days Inn by Wyndham Brooksville/Dade City

2 out of 5
6320 Windmere Rd Brooksville FL
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $84 total per night
$84 total
Jan 14 - Jan 15
Total with taxes and fees
This motel features an outdoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Pool
Breakfast included
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
$108 nightly
The price is $116 total per night
$116 total
Jan 18 - Jan 19
Total with taxes and fees
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
WoodSpring Suites Orlando West - Clermont

WoodSpring Suites Orlando West - Clermont

2.5 out of 5
16311 FL-50 Clermont FL
Free Cancellation
Reserve now, pay when you stay
$69 nightly
The price is $77 total per night
$77 total
Jan 14 - Jan 15
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Laundry facilities are provided for your convenience.
Pet friendly
Parking included
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
Free Cancellation
Reserve now, pay when you stay
$82 nightly
The price is $91 total per night
$91 total
Jan 18 - Jan 19
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. A safe deposit box is provided and the front desk is staffed around-the-clock.
Breakfast included
Parking included
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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.

Popular places to visit

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 are vacation packages to Webster?
Enjoy an unforgettable travel experience in Webster with a vacation package starting from as low as $300. Organizing your tours, hotels and flights with Travelocity is so simple. And even better, our great deals will leave you with more cash in your pocket for fun, fun, fun!
Where can I get the best vacation package deals for Webster?
For an amazing package deal to Webster, book with Travelocity. Choose from 400 partner airlines and 1,000,000 properties across the globe to create your ultimate adventure — it couldn't be simpler.
Why should I purchase my Webster vacation package via Travelocity?
Whether you're searching for the ultimate unplugged vacation or you crave the fun and excitement of the big smoke, booking everything with Travelocity saves you time, money and hassle. No need to sift through hundreds of websites looking for the best deal — our Price Match Guarantee ensures you'll always get the lowest price, and our professional customer service experts are available 24/7 should you need anything at all.
Can I save on my Webster car rental if I combine it with my hotel or flight?
With a Webster vacation package, you can bundle your flight, hotel and car bookings and save a whole lot. If you can't wait to uncover the best of this wonderful location, why not check out Universal Studios Florida? This top sight is 35 mi from Webster. With your own wheels, you'll be there in a flash.
Which airport is best for Webster?
Orlando Intl. Airport (MCO) is popular. It's located approximately 45 mi east of Webster. Other options worth considering are Tampa Intl. Airport (TPA) (55 mi away from central Webster) and Orlando Sanford Intl. Airport (SFB) (50 mi away from central Webster).
What is there to do in Webster?
Webster Westside Flea Market should be at the top of your itinerary. Once you've crossed off this well-known attraction, simply roam the streets of Webster and discover what makes this wonderful destination tick.
Where should I stay when visiting Webster?
If you're looking for somewhere to base yourself, consider the River Daze Cabin - A cozy cabin right on the river. It's the top pick for many travelers.

Photos of local treasures

Browse Webster vacation photos for more inspiration