Hemingway Holidays

Book a Hotel + Flight or Car together to unlock savings

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

Lake Sumter Landing

1 out of top 10 points of interest in this area

Though Lake Sumter Landing may 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 hotels in Lake Sumter Landing

Top hotels in Hemingway

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 3.590.746 ₫ per night from 26 Apr to 27 Apr
3.590.746 ₫
3.842.098 ₫ total
26 Apr - 27 Apr
includes taxes & fees
9.8/10 Exceptional! (1,155 reviews)
Expected windows to at least open with the pool view. Loved the dimmers on the light switches. Made great night lights.

Reviewed on 9 Apr 2026

Brownwood Hotel & Spa
The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
The price is 3.057.029 ₫ per night from 3 May to 4 May
3.057.029 ₫
3.271.020 ₫ total
3 May - 4 May
includes taxes & fees
9.2/10 Wonderful! (1,369 reviews)
The room was clean, Staff was helpful did not use any of amenities or bar

Reviewed on 11 Apr 2026

The Waterfront Inn
Hotel Eastport

Hotel Eastport

2 out of 5
7065 Beebe Court Wildwood FL
Fully refundableReserve now, pay when you stay
The price is 3.923.319 ₫ per night from 27 Apr to 28 Apr
3.923.319 ₫
4.197.951 ₫ total
27 Apr - 28 Apr
includes taxes & fees
9.6/10 Exceptional! (119 reviews)
The hotel is beautiful! We could not have asked for a better place. It’s proximity to our venue and all the activities happening around the hotel made it the perfect place to stay.The breakfast offerings are just enough. The best part about the stay was the friendly staff. I highly recommend this ...

Reviewed on 12 Apr 2026

Hotel Eastport
See all 2,256 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.

Frequently asked questions

How much does a Hemingway holiday package cost?
Go from wondering to wandering with our Hemingway holiday packages, which start from a low . 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 holiday 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 1null000null000 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 Holiday Home With Golf Cart - 2 Bed 2 Bath. Both offer comfy beds and are popular options with lots of travellers.
How far in advance should I book my Hemingway holiday?
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 holiday!
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. Holidaying 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 holiday 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 holiday package?
Whether it's your hotel or flight, you can cancel or change it. Booked your Hemingway holiday 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.

Popular places to visit

The Villages Market Square

You can browse for the perfect souvenirs at The Villages Market Square during your trip to The Villages. Wander the lakeside in this quaint area.

The Villages Market Square

Cane Garden Country Club

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

Cane Garden Country Club

Glenview Champions Country Club

Enjoy a round of golf in The Villages at Glenview Champions Country Club. While in this family-friendly area, you can savour the top-notch restaurants.

Glenview Champions Country Club