Sumter County Vacations & Trips from $325
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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 destinations in Sumter County
The Latest Sumter County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort
$325
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (2,045 reviews)
We was told they didn’t have breakfast there and you have to pay for water park it started raining we didn’t get any money back I was also told me and my family would have side by side rooms and unfortunately we didn’t 😡😡
Reviewed on Sep 11, 2026
The Delaney Hotel
South Orange
$573
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.6/10 Exceptional! (1,202 reviews)
The hotel was very quaint, just make sure they dont give you a room facing the street. We heard sirens all night. The beds are super comfortable, and housekeeping is right on the job.
Reviewed on Sep 9, 2026
Find the Best Sumter County Vacation Packages
Sumter County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Orlando Intl. Airport (MCO) |
Top Sights | Dade Battlefield State Park, Lake Deaton and The Florida International Teaching Zoo |
Sumter County Hotel Deals
The Waterfront Inn
1105 Lake Shore Drive The Villages FL
$94 nightly
$101 total
Sep 16 - Sep 17
Total with taxes and fees
Brownwood Hotel & Spa
3003 Brownwood Blvd Wildwood FL
Fully refundableReserve now, pay when you stay
$105 nightly
$112 total
Sep 30 - Oct 1
Total with taxes and fees
9.8/10 Exceptional! (1,396 reviews)
"There’s nothing wrong with this place other than breakfast is not included. Very comfort and nice. Staff always helpful. Recommend 100%"
Reviewed on Sep 10, 2026
Holiday Inn Express & Suites Wildwood The Villages by IHG
928 East State Road 44 Wildwood FL
Fully refundable
$83 nightly
$89 total
Sep 28 - Sep 29
Total with taxes and fees
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 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.
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.
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.
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.
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.
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.
What to do in Sumter County
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
