Sumter County Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

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

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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

FlightsFlightsHotelsHotels

The Villages

The Villages
FlightsFlightsHotelsHotels

Wildwood

Wildwood

Top Sumter County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was CA $1,648, price is now CA $823 per person
CA $823
per person
Mar 22 - Mar 29
found 24 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8/10 Very Good! (1,367 reviews)
Room was amazing, all though the jacuzzi jets were dirty so once i turned them on the water got really gross. They need to do better at cleaning. I was certainly disappointed because i got the room for the jacuzzi and didn’t get to use it because it was filthy.

Reviewed on Feb 5, 2026

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was CA $3,451, price is now CA $1,387 per person
CA $1,387
per person
Apr 17 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8/10 Very Good! (1,703 reviews)
Great resort, family friendly, lots of activities

Reviewed on Feb 8, 2026

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

3 out of 5
Town 'n' Country
Price was CA $2,064, price is now CA $976 per person
CA $976
per person
Apr 18 - Apr 25
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Tampa (TPA)
2/10 (4 reviews)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was CA $2,212, price is now CA $1,072 per person
CA $1,072
per person
Apr 16 - Apr 23
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.8/10 Excellent! (1,085 reviews)
Apartment was clean and spacious.

Reviewed on Feb 8, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $1,831, price is now CA $912 per person
CA $912
per person
Mar 22 - Mar 29
found 24 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8.2/10 Very Good! (5,482 reviews)
Was ok, dont recall expecting 30$ plus tax daily "resort" fee when booking. Also waterpark feature of the resort was closed for the season understandably due to chilly weather but that leads back to again, why resort fee?

Reviewed on Feb 8, 2026

Sumter County Hotel Deals

The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
9.2/10 Wonderful! (1,312 reviews)
Nice staff, view of lake.

Reviewed on Feb 1, 2026

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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
9.6/10 Exceptional! (1,105 reviews)
Clean. Courteous staff. Great location

Reviewed on Feb 6, 2026

Get rates
Brownwood Hotel & Spa
Holiday Inn Express & Suites Wildwood The Villages by IHG

Holiday Inn Express & Suites Wildwood The Villages by IHG

3.5 out of 5
928 East State Road 44 Wildwood FL
Fully refundable
The price is CA $174 per night from Mar 8 to Mar 9
CA $174
CA $186 total
Mar 8 - Mar 9
includes taxes & fees
9.4/10 Exceptional! (1,006 reviews)
staff

Reviewed on Feb 3, 2026

Holiday Inn Express & Suites Wildwood The Villages by IHG
See all 1,441 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $823. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.