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*

  • 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

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

Madison Blue Springs at Sunset, Madison Blue Springs State Park, Florida
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Wildwood

Wildwood
Beautiful sunset over the lake at The Villages in Leesburg, Florida creating a serene evening atmosphere
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The Villages

The Villages

Top Sumter County Vacation Deals

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

Westgate Towers Resort

3.5 out of 5
Price was CA $910, price is now CA $472 per person
CA $472
per person
Jun 5 - Jun 10
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (1,004 reviews)
Hotel rooms are spacious. Right in a rear location. Walmart is 3 min drive, CVS across the street. Hot tbs ar lean, pool is clean. For people who don’t read, there is no room service, have to ask for any extra items.

Reviewed on Mar 25, 2026

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was CA $1,712, price is now CA $550 per person
CA $550
per person
May 2 - May 7
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8.2/10 Very Good! (5,182 reviews)
Fantastic value. Clean, comfortable and great location.

Reviewed on Mar 26, 2026

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was CA $2,064, price is now CA $954 per person
CA $954
per person
Jun 4 - Jun 16
found 13 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8/10 Very Good! (1,510 reviews)
Business friendly. Pet friendly. Clean room. Lots of staff at facility.

Reviewed on Mar 25, 2026

Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was CA $1,099, price is now CA $562 per person
CA $562
per person
Jun 5 - Jun 10
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (1,005 reviews)
Best stay ever ! For now on this is the only place we are booking when coming to Orlando . Thank you for everything.

Reviewed on Mar 22, 2026

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
International Drive District
Price was CA $1,290, price is now CA $743 per person
CA $743
per person
Jun 5 - Jun 10
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
7.8/10 Good! (381 reviews)
Shuttle never picked us up after scheduling. Long lines for breakfast approx. 20-30 min

Reviewed on Mar 23, 2026

Sumter County Hotel Deals

The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
The price is CA $207 per night from Apr 8 to Apr 9
CA $207
CA $222 total
Apr 8 - Apr 9
includes taxes & fees
9.2/10 Wonderful! (1,345 reviews)
Wonderful place wonderful atmosphere

Reviewed on Mar 25, 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 CA $227 per night from Mar 30 to Mar 31
CA $227
CA $243 total
Mar 30 - Mar 31
includes taxes & fees
9.8/10 Exceptional! (1,133 reviews)
Great stay again. Friendly staff, always helpful. Comfortable bed & clean room - everything I was expecting from a nice hotel stay.

Reviewed on Mar 24, 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 CA $219 per night from Mar 30 to Mar 31
CA $219
CA $234 total
Mar 30 - Mar 31
includes taxes & fees
9.6/10 Exceptional! (82 reviews)
Beautiful hotel, very clean, friendly staff.

Reviewed on Mar 25, 2026

Hotel Eastport
See all 1,454 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
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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 $472. 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.