Sumter County Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
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Your Sumter County Vacation
Book a vacation package to Sumter County and make travel planning a cinch. With all the details arranged before you leave, you can focus on enjoying every moment in this exciting destination. Get your trip to Sumter County off to a flying start by heading to its most famous cities. Wildwood is one you shouldn't miss. Start packing your suitcase, because your Sumter County vacation is just a few clicks away with Expedia.
Top vacation destinations in Sumter County
The Villages
Wildwood
Top Sumter County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
CA $2,280
per person
Nov 20 - Nov 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)
The property was conveniently located by plenty of food options, activities and near all theme parks such as Disney seaworld and universal. Plenty of parking and the staff were amazing.
Reviewed on Oct 7, 2026
Sumter County Hotel Deals
The Waterfront Inn
1105 Lake Shore Drive The Villages FL
CA $153
CA $163 total
Nov 1 - Nov 2
includes taxes & fees
9.4/10 Exceptional! (1,532 reviews)
"A favorite place to stay! Make sure and try out Calypso restaurant!"
Reviewed on Oct 8, 2026
Brownwood Hotel & Spa
3003 Brownwood Blvd Wildwood FL
Fully refundableReserve now, pay when you stay
CA $194
CA $207 total
Nov 5 - Nov 6
includes taxes & fees
Holiday Inn Express & Suites Wildwood The Villages by IHG
928 East State Road 44 Wildwood FL
Fully refundable
CA $129
CA $139 total
Nov 1 - Nov 2
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"This is our go-to stop when traveling from our home and West Palm Beach. Everything is always so clean and the front desk staff are always so nice and cheerful!!! It’s so quiet and peaceful there. We love it!!"
Reviewed on Oct 9, 2026
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.
Frequently asked questions
How much does a Sumter County vacation package cost?
We make it easy to explore the world, with Sumter County packages starting from just CA $752. You'll have the flexibility to bundle your preferred airlines, hotels and car rental. For the ultimate escape, why not add a couple of experiences and tours to your itinerary?
How do I get a cheap travel package to Sumter County?
Secure flights that fit your busy schedule, add a hotel room to your booking and see how much you save with a Sumter County vacation package. It's as simple as that! From flights and hotels to rental cars and tours, Expedia makes traveling on a budget easy. And with over 550 partner airlines and 1,000,000 hotels all over the world to select from, you'll never be short of choice.
What are the top hotels in Sumter County?
For hotels in The Villages with friendly service and cozy beds, you can't beat Hilton Daytona Beach Oceanfront Resort and Daytona Grande Oceanfront Resort. If you're visiting Wildwood as well, you can look forward to a great night's sleep at Margaritaville Jacksonville Beach or The Island Resort at Fort Walton Beach.
How far in advance should I book my Sumter County vacation?
Reserving your flight early with Expedia means one less thing to have to worry about. Most air carriers display prices up to 12 months prior to take off. Generally, this is the cheapest time to book. If circumstances have left you booking late, incredible deals to Sumter County occasionally appear a few weeks before departure.
What does an Expedia Sumter County travel package include?
It's up to you! You can choose from a variety of Sumter County packages, such as a flight, rental car and hotel. You can also book a hotel and a flight, or a flight and a rental car. Once you've made your booking, you can add on the fun stuff like tours and activities. Whatever your Sumter County vacation looks like, you'll save!
What should I know before booking a Sumter County travel package?
You'll enjoy excellent savings when you combine your hotels, flights and rental cars into a travel package. Not just that, booking everything in one spot will make your trip planning easier. So why waste your time or money? Whether you're organizing a ritzy romantic getaway or a low-cost family road trip, browse our vacation packages today.
Can I choose my airline with a Sumter County Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines around the world. Our vacation packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Sumter County vacation package?
You sure can, and we'll help you every step of the way. You may be able to change or cancel your Sumter County vacation package for free if you booked in the last 24 hours. However, you may incur a fee from your airline, hotel or car rental company if your booking is older than that. If your travel plans unexpectedly change, take a look at our Customer Service Portal for more information.
Stay near popular Sumter County attractions
Brownwood Paddock Square
You can enjoy retail therapy at Brownwood Paddock Square during your visit to Wildwood. Discover the live music and shops in this family-friendly area.
The Villages Market Square
9.2/10 (669 reviews)
You can enjoy retail therapy at The Villages Market Square during your visit to The Villages. Wander the lakeside in this quaint area.
Webster Westside Flea Market
8.4/10 (40 reviews)
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.
Glenview Champions Country Club
9.0/10 (43 reviews)
Enjoy a round of golf in The Villages at Glenview Champions Country Club. While in this family-friendly area, you can savor the top-notch restaurants.
Lake Sumter
Commune with nature and explore the great outdoors at Lake Sumter during your travels in The Villages. While in this walkable area, you can savor the top-notch restaurants.
Cane Garden Country Club
9.0/10 (55 reviews)
Enjoy a round of golf in The Villages at Cane Garden Country Club. Discover the coffeehouses and entertainment venues in this quaint area.
Continental Country Club
8.0/10 (39 reviews)
Enjoy a round of golf in Wildwood at Continental Country Club. Discover the coffeehouses and entertainment venues in this quaint area.
Lake Okahumpka Park
8.6/10 (38 reviews)
Explore the great outdoors at Lake Okahumpka Park, a lovely green space in Wildwood. Discover the entertainment venues in this quaint area, or seek out its golf courses.
What to do in Sumter County
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
