Leesburg Vacation Packages 2026 from $255

Leesburg flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Westgate Towers Resort

Save 100% on your flight

$255

per person

Oct 6 - Oct 11

found 1 day ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

2 outdoor pools, 2 hot tubs, and a gym are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Westgate Palace Hotel / Universal / I-Drive

International Drive District

Save 100% on your flight

$379

per person

Oct 4 - Oct 7

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

This resort features an outdoor pool, a gym, and a restaurant. Bring the family and enjoy the children's pool, free theme park shuttle, and kid-friendly dining. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi.

Westgate Vacation Villas Resort

Save 100% on your flight

$306

per person

Oct 2 - Oct 6

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.

Seasons Florida Resort

Save 100% on your flight

$257

per person

Oct 16 - Oct 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and laundry facilities are also provided.

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight

$1,168

per person

Sep 2 - Sep 8

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.

Top Leesburg hotels deals

Microtel Inn & Suites by Wyndham Leesburg/Mt Dora

9700 Us Highway 441 Leesburg FL

Free Cancellation

Reserve now, pay when you stay

$68 nightly

$75 total

Aug 2 - Aug 3

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

Wingate by Wyndham Leesburg Florida

2476 N. Citrus Blvd Leesburg FL

Free Cancellation

Reserve now, pay when you stay

$63 nightly

$70 total

Jul 26 - Jul 27

Total with taxes and fees

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Business travelers can take advantage of the business center. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

TownePlace Suites by Marriott Leesburg

238 Eagles Watch Street Leesburg FL

Free Cancellation

Reserve now, pay when you stay

$105 nightly

$117 total

Jul 26 - Jul 27

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

Quality Inn & Suites Leesburg Chain of Lakes

1392 North Blvd W Leesburg FL

Free Cancellation

$57 nightly

$64 total

Jul 27 - Jul 28

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. Enjoy the outdoor pool and conveniences like a 24-hour front desk and barbecue grills.

Pool

Breakfast included

Hampton Inn Leesburg/Tavares

9630 Us Highway 441 Leesburg FL

Free Cancellation

Reserve now, pay when you stay

$90 nightly

$100 total

Aug 2 - Aug 3

Total with taxes and fees

This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Pool

Breakfast included

Best Western Plus Chain of Lakes Inn & Suites

1321 N 14th St Leesburg FL

Free Cancellation

Reserve now, pay when you stay

$93 nightly

$103 total

Aug 2 - Aug 3

Total with taxes and fees

This hotel features an outdoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like full breakfast and free self parking.

Pool

Hot Tub

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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.

Stay near popular Leesburg attractions

A beach at sunset with silhouettes of people and a pink frisbee on the sand.

Treasure Island

Commune with nature and explore the great outdoors at Treasure Island during your travels in Leesburg. Visit the area's shops or amble around its lakeside.

See properties

Leesburg Vacations

Known as the Lakefront City, Leesburg offers a different type of vacation than you might expect from other Florida destinations. Located on Lake Harris and just 44.5 miles from Orlando, this small city has something for everyone. From historic landmarks to modern shopping locations, you are sure to find plenty to see and do. Leesburg rental cars let you experience the city and surrounding areas at your own pace.

Major Attractions

Leesburg vacation packages allow you to enjoy all the great local sights without breaking your budget. Explore the famous canals and gardens of the Venetian Gardens lakeside park. Lake Square Mall provides all the shopping opportunities you can handle, and make sure to include a trip to the historic Mote-Morris House. This marvelous two-story building has been standing since 1892. The doors are open to the public twice a month, and you can rent rooms to host your next family reunion or special event.

Recurring Festivals and Events

Leesburg vacations aren't complete without attending one of the city's annual festivals. The largest and most popular is the Leesburg Bikefest. Over a quarter of a million people from all around the country attend this springtime event each year. The three-day festival is held in late April and features some of the biggest bands around. Enjoy live entertainment, death-defying motorcycle acts, and beautiful bikes in all shapes and sizes. You can show off your own bike, or just admire the miraculous machines created by others. Hotels in Leesburg fill up quickly during the festival, so make sure to book early.

Browse Travelocity's extensive selection of Leesburg packages to find one to suit your needs, and enjoy your Florida vacation in style. Booking your flight and hotel at the same time can save you up to $537, leaving you more spending money for the fun stuff.

Frequently asked questions

How much are vacation packages to Leesburg?

You might be surprised — you can find yourself in Leesburg for as little as $255. Allow Travelocity to save you time and stress with our awesome vacation package deals. With flights, hotels and tours all ready to go at our one-stop shop, what's holding you back?

How long should my Leesburg vacation be?

Most travelers choose to spend around 3 nights in Leesburg, but how long you stay is your choice. If you want to discover all the incredible things this place has to offer, why not hang around a while longer?

Where can I get the best vacation package deals for Leesburg?

For a fun and affordable package deal to Leesburg, you can't go past Travelocity. Select from 400 partner airlines and 1,000,000 properties around the globe to create your dream trip — it's really that simple.

Why should I purchase my Leesburg vacation package via Travelocity?

From exciting destinations to one-of-a-kind experiences, we have everything you need to satisfy your wanderlust. Our friendly 24/7 customer support will also ensure you're being taken care of while you're on your getaway. And don't worry if you spot a better price on your reservation, we'll match it. That's our Price Match Guarantee.

Will I save money on my Leesburg car rental if I bundle it with hotels and flights?

Certainly — combine your car, flight and hotel into a Leesburg vacation package and you'll save loads. With so much to uncover in the Leesburg area, that set of wheels will come in handy. Once you're behind the wheel, crank up the tunes and head to Universal Studios Florida, a must-see attraction roughly 35 mi from Leesburg.

Which airport is best for Leesburg?

Orlando Intl. Airport (MCO) is one of the busiest airports in Leesburg. It's roughly 45 mi southeast of the bustling downtown area. Other choices include Daytona Beach Intl. Airport (DAB) (55 mi away from central Leesburg) and Orlando Sanford Intl. Airport (SFB) (40 mi away from central Leesburg).

What is there to do in Leesburg?

Leesburg has plenty of things to see and do, such as Paquette's Historical Farmall Museum and Plantation Golf Club. These renowned attractions are at the top of most tourists' must-see lists.

Where should I stay when visiting Leesburg?

The TownePlace Suites by Marriott Leesburg is recommended by many travelers. Book as soon as possible before it's too late.

Where to stay in Leesburg: Best areas for travelers

The Villages: From The Waterfront Inn or the Location! Villages Ranch Home, Gas Golf Cart, Walk to Pool, it'll be a breeze to see the sights of this neighborhood. Feel your best in nature? Get out and appreciate Lake Deaton. The Property Near Sumpter Landing is another welcoming option if you're hoping to stay on this side of town.
Wildwood: The Comfort Inn & Suites Wildwood - The Villages, The Country Porch in Wildwood Florida - A Stones Throw Away From The Villages! and the Days Inn by Wyndham Wildwood I-75 are terrific choices if you want to stay here. You'll be able to quickly get back to your hotel after a big day of wandering around the local attractions. Miona Lake Golf Club is just one of those sights to put on your must-see list.
Lady Lake: When you've finished checking out the local sights and sounds, slip on your pajamas and slide into bed at the Microtel Inn & Suites by Wyndham Lady Lake/The Villages. The Hampton Inn & Suites Lady Lake/The Villages is another great place to stay.
Tavares: Settle into this neighborhood and have Lake Dora, Wooten Park and Lake County Historical Museum right at your doorstep. The Standard King, the King and Queen Bed Balcony Lake View #5 and the Two Bedroom Suite are a few options to jump into bed in this part of town.