Sumter County Holidays

Photo by Brian V. Rowe

  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Sumter County

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$157 per night from 24 Jun to 25 Jun
S$157
24 Jun - 25 Jun
includes taxes & fees
9.8/10 Exceptional! (1,193 reviews)
"The whole place was very clean, staff was helpful, beautifully decorated"

Reviewed on 25 May, 2026

Brownwood Hotel & Spa
The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
The price is S$162 per night from 31 May to 1 Jun
S$162
31 May - 1 Jun
includes taxes & fees
9.2/10 Wonderful! (1,408 reviews)
"It was a pleasant surprise for us, exceeding our expectations."

Reviewed on 22 May, 2026

The Waterfront Inn
Hampton Inn & Suites Lady Lake/The Villages

Hampton Inn & Suites Lady Lake/The Villages

3 out of 5
11727 Ne 63 Rd Dr Lady Lake FL
Fully refundableReserve now, pay when you stay
The price is S$134 per night from 28 May to 29 May
S$134
28 May - 29 May
includes taxes & fees
Hampton Inn & Suites Lady Lake/The Villages
See all 1,410 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.

* 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.