Hemingway Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Top Holiday Package Deals in Hemingway
Price found within the past 48 hours. Click for updated prices.
Where to stay in Hemingway
Find the best Hemingway areas and neighborhoods for the activities you enjoy most. Learn more about Hemingway
Lake Sumter Landing
1 out of top 10 points of interest in this area
While visiting Lake Sumter Landing, you might make a stop by sights like The Villages Market Square and Lake Sumter.
Virginia Trace
While Virginia Trace isn't home to many top sights, The Villages Market Square and Lake Sumter are some notable places to visit nearby.
Sunset Pointe
Though Sunset Pointe might not have many top sights, you can venture to the surrounding area to see attractions like Cane Garden Country Club and The Villages Market Square.
Duval
While Duval isn't home to many top sights, Cane Garden Country Club and The Villages Market Square are some notable places to visit nearby.
Bonita
While Bonita might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Cane Garden Country Club and The Villages Market Square.
Hemingway Hotel Deals
The Waterfront Inn
1105 Lake Shore Drive The Villages FL
CA $158
CA $169 total
Nov 1 - Nov 2
includes taxes & fees
9.4/10 Exceptional! (1,544 reviews)
"Wonderful overnight stay! We will stay longer next visit!"
Reviewed on Oct 25, 2026
Brownwood Hotel & Spa
3003 Brownwood Blvd Wildwood FL
Fully refundableReserve now, pay when you stay
CA $194
CA $207 total
Nov 12 - Nov 13
includes taxes & fees
9.8/10 Exceptional! (1,478 reviews)
"Beautiful Hotel! Very CLEAN!!"
Reviewed on Oct 25, 2026
The Citrus on the Lake
199 W Ruby Street Tavares FL
CA $188
CA $208 total
Oct 27 - Oct 28
includes taxes & 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.
Frequently asked questions
How much does a Hemingway vacation package cost?
Go from wondering to wandering with our Hemingway vacation packages, which start from a low CA $788. Select the hotels and flights that suit your plans. Then, add on a couple of activities or tours for an amazing escape.
How do I get a cheap travel package to Hemingway?
Book everything in the one place with our Hemingway vacation packages. You'll find deals on flights, hotels and more that'll keep your pocket happy and your adventurous spirit alive. And, with more than 550 air carriers and 1,000,000 properties around the world to select from, you'll have endless opportunities to mix and match however you please.
Where should I stay in Hemingway?
An escape to Hemingway isn't complete without stopping by The Villages Market Square. Why not choose a hotel within walking distance of this fantastic attraction?
What are the top hotels in Hemingway?
If this will be your first visit to Hemingway, book a room at Welcome To The Life or Vacation Home With Golf Cart - 2 Bed 2 Bath. Both offer comfy beds and are popular options with lots of travelers.
How far in advance should I book my Hemingway vacation?
Reward yourself with the biggest variety and the lowest prices by booking your Hemingway adventure nice and early. Airlines generally publish flights anywhere up to 12 months before departure, so start your planning as soon as possible. That being said, Expedia is committed to giving you the best deals around, so it's always a good time to book your dream vacation!
What does an Expedia Hemingway travel package include?
From flights and hotels to rental cars, Expedia can help you shape a Hemingway package that's ideal for you. Vacationing for a few weeks? Check out a rental car, hotel and flight bundle. If you're taking a quick break, a flight and hotel deal could be more your style. Experiences can also be added once you've made your booking. Our packages make it easy to plan and save.
What should I know before booking a Hemingway travel package?
Our prices are always low. However, you'll pick up even more savings when you book your hotels, flights and car rentals together. With an Expedia package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Hemingway Expedia vacation package?
Expedia has access to more than 550 airline partners worldwide, so you certainly can. Just choose your preferred air carrier and create the perfect Hemingway trip.
If I'm not able to travel, can I cancel my Hemingway vacation package?
Whether it's your hotel or flight, you can cancel or change it. Booked your Hemingway vacation package in the last 24 hours? You may be able to make any changes for free. If it's been longer than that, you may be charged a fee by your hotel, airline or car rental company. For further information, head to our Customer Service Portal. We'll help you every step of the way.
Things to do
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.