Sumter County Holidays

Photo by Brian V. Rowe

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    Save up to S$1,300 when you book a flight and hotel together*

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Top hotels in Sumter County

The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
The price is S$136 per night from 14 Jul to 15 Jul
S$136
14 Jul - 15 Jul
includes taxes & fees
9.2/10 Wonderful! (1,443 reviews)
"The pool area was great, location of property was convenient walking to local restaurants and shops"

Reviewed on 9 Jul, 2026

The Waterfront Inn
Brownwood Hotel & Spa

Brownwood Hotel & Spa

3 out of 5
3003 Brownwood Blvd Wildwood FL
Fully refundableReserve now, pay when you stay
The price is S$148 per night from 21 Jul to 22 Jul
S$148
21 Jul - 22 Jul
includes taxes & fees
9.8/10 Exceptional! (1,263 reviews)
"Place is always clean and service is always outstanding. Will return every time we’re in the area."

Reviewed on 8 Jul, 2026

Brownwood Hotel & Spa
Hotel Eastport

Hotel Eastport

2 out of 5
7065 Beebe Court Wildwood FL
Fully refundableReserve now, pay when you stay
The price is S$154 per night from 27 Jul to 28 Jul
S$154
27 Jul - 28 Jul
includes taxes & fees
Hotel Eastport
See all 1,430 properties in Sumter County
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 holiday package cost?
We make it easy to explore the world, with Sumter County packages starting from just . 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 holiday package. It's as simple as that! From flights and hotels to rental cars and tours, Expedia makes travelling 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 cosy 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 holiday?
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 holiday 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 organising a ritzy romantic getaway or a low-cost family road trip, browse our holiday packages today.
Can I choose my airline with a Sumter County Expedia holiday package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines around the world. Our holiday 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 holiday 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 holiday 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 do some window-shopping at Brownwood Paddock Square during your visit to Wildwood. Discover the live music and shops in this family-friendly area.
See properties

What to do in Sumter County

Gypsy Gold Horse Farm Tour

Gypsy Gold Horse Farm Tour

S$71
per adult
100% of travellers recommend
Gypsy Gold Horse Farm Tour
See all activities in Sumter County

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.