Hemingway Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Hemingway

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
per person
Nov. 14 - Nov. 18
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8/10 Very Good! (4,616 reviews)
Very safe and cozy will visit again

Reviewed on Sep. 26, 2024

Costa d'Este Beach Resort and Spa

Costa d'Este Beach Resort and Spa

4 out of 5
Central Beach
Save 100% on your flight
per person
Nov. 5 - Nov. 12
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
9.2/10 Wonderful! (1,000 reviews)
Everyone was amazing!!!!!!

Reviewed on Sep. 23, 2024

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Florida Center
Save 100% on your flight
per person
Nov. 28 - Dec. 5
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.4/10 Very Good! (1,000 reviews)
Very clean and close to everything

Reviewed on Sep. 14, 2024

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
per person
Dec. 1 - Dec. 8
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
7.8/10 Good! (3,844 reviews)
I really enjoyed the property. Although it was work related versus leisure, I am considering it for a future family vacation.

Reviewed on Sep. 25, 2024

Harbor Island Beach Club by Villatel

Harbor Island Beach Club by Villatel

4 out of 5
Save 100% on your flight
per person
Dec. 7 - Dec. 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Orlando (MCO)
No reviews

Where to stay in Hemingway

Find the best Hemingway areas and neighborhoods for the activities you enjoy most. Learn more about Hemingway
Default Image

Lake Sumter Landing

1 out of top 10 points of interest in this area

Though Lake Sumter Landing might not have many top sights, you can venture to the surrounding area to see attractions like The Villages Market Square and Cane Garden Country Club.

Find hotel + flight trips in Lake Sumter Landing

Hemingway Hotel Deals

The Waterfront Inn
The Waterfront Inn
3 out of 5
1105 Lake Shore Drive, The Villages, FL
The price is CA $144 per night from Oct. 1 to Oct. 2
CA $144
CA $155 total
includes taxes & fees
Oct 1 - Oct 2
8.8/10 Excellent! (1,000 reviews)
"The restaurant and pool were still under renovation. No problem. Many other places to eat within a few minutes walk. I loved walking along the lake in the mornings. Very beautiful sunsets in the evenings"

Reviewed on Sep. 22, 2024

The Waterfront Inn
Microtel Inn & Suites by Wyndham Leesburg/Mt Dora
Microtel Inn & Suites by Wyndham Leesburg/Mt Dora
2 out of 5
9700 Us Highway 441, Leesburg, FL
Fully refundableReserve now, pay when you stay
The price is CA $108 per night from Sep. 29 to Sep. 30
CA $108
CA $120 total
includes taxes & fees
Sep 29 - Sep 30
8.4/10 Very Good! (1,004 reviews)
"MOST WAS OK, HOWEVER THE HALLWAYS HAD A STRONG ODOR."

Reviewed on Sep. 19, 2024

Microtel Inn & Suites by Wyndham Leesburg/Mt Dora
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 $181 per night from Sep. 29 to Sep. 30
CA $181
CA $193 total
includes taxes & fees
Sep 29 - Sep 30
9.6/10 Exceptional! (1,004 reviews)
"The thing that I didn’t like was the pool closes at 9 pm even on friday and Saturday night which we were allowed to stay at the pool the next day after checkout… everything else was AWESOME and we will definitely be returning"

Reviewed on Sep. 23, 2024

Brownwood Hotel & Spa
See all 1,839 properties in Hemingway
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 Hemingway vacation package cost?
Go from wondering to wandering with our Hemingway vacation packages, which start from a low CA $645. 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.

Discover the most popular places to visit in Hemingway

Image for The Villages Market Square

The Villages Market Square

4.5/5(2 reviews)

You can enjoy retail therapy at The Villages Market Square during your visit to The Villages. Wander the lakeside in this quaint area.

The Villages Market Square
Image for Nancy Lopez Legacy Golf & Country Club

Nancy Lopez Legacy Golf & Country Club

Enjoy a round of golf in The Villages at Nancy Lopez Legacy Golf & Country Club. While in this family-friendly area, you can savor the top-notch restaurants.

Nancy Lopez Legacy Golf & Country Club
Image for Cane Garden Country Club

Cane Garden Country Club

Enjoy a round of golf in The Villages at Cane Garden Country Club. Discover the coffeehouses and entertainment venues in this quaint area.

Cane Garden Country Club

Things to do

Image for Gypsy Gold Horse Farm Tour

Gypsy Gold Horse Farm Tour

CA $76
Per adult
100% of travellers recommend
Gypsy Gold Horse Farm Tour
See all activities in The Villages

Other vacations you might like

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