Caroline Holidays

  • Plan, book, travel with confidence
    • payments icon
    Better together
    Save up to S$134 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
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Where to stay in Caroline

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

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 Caroline

The Waterfront Inn
The Waterfront Inn
3 out of 5
1105 Lake Shore Drive, The Villages, FL
The price is S$200 per night from 26 Nov to 27 Nov
S$200
includes taxes & fees
26 Nov - 27 Nov
8.8/10 Excellent! (1,007 reviews)
"Newly redone. Very clean. Our room was nicely designed in a rather “sparse” way…..but that only contributed to the feeling of cleanliness and less clutter. Stay there when visiting relatives in The Villages. Perfect location."

Reviewed on 23 Nov,2024

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 S$244 per night from 1 Dec to 2 Dec
S$244
includes taxes & fees
1 Dec - 2 Dec
9.6/10 Exceptional! (1,006 reviews)
"Great business trip stay at Brownwood Hotel and Spa! Clean, convenient, staff friendly, restaurant is great! Highly recommend!"

Reviewed on 23 Nov,2024

Brownwood Hotel & Spa
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 S$125 per night from 1 Dec to 2 Dec
S$125
includes taxes & fees
1 Dec - 2 Dec
8.4/10 Very Good! (1,001 reviews)
"The room was very clean and comfortable. I had a concerned about bedbugs, and i was told they have a pest control service to make sure rooms are clean and free of it. I will be staying at this place again."

Reviewed on 17 Nov,2024

Microtel Inn & Suites by Wyndham Leesburg/Mt Dora
See all 1,873 properties in Caroline
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 Caroline holiday package cost?
The cheapest Caroline holiday package is , so the trip of your dreams can become a reality — without spending an arm and a leg. Bundle flights, hotels and car rentals to custom build a package suited to your travelling style.
How do I get a cheap travel package to Caroline?
Book everything all in one place with our Caroline holiday packages. You’ll discover bargains on flights, hotels and more that’ll keep your travel budget happy and your spirit of adventure alive. And, with more than 550 airlines and 1,000,000 hotel options throughout the world to select from, you’ll have the flexibility to mix and match as you want.
Where should I stay in Caroline?
There’s loads to do in Caroline, so spend your nights near its best attractions and treat yourself to more time sightseeing. The Villages Market Square is one place to put on your must-see list.
What are the top hotels in Caroline?
Family Fun, , Nr Pool And Ice Cream And Town and Great 3 Bedroom With Complimentary Use Of Golf Cart are among the most popular hotels in Caroline. Why not look up the amenities and rates at each and then decide?
How far in advance should I book my Caroline holiday?
Search Expedia to compare international airfares as soon as you’ve got your travel dates. You can generally purchase a ticket up to 12 months in advance. If you don’t see your preferred carrier, or you’ve left things to the last moment, don’t despair. Cheap tickets to Caroline sometimes occur within weeks of departure.
What does an Expedia Caroline travel package include?
Travel packages include hotels, rental cars and flights, but you can combine any of them to create your dream Caroline trip. You can also add on activities and tours once you’ve made your booking. You’re in the driver’s seat! When you combine your bookings with Expedia, you’ll get access to discounts you won’t find anywhere else.
What should I know before booking a Caroline travel package?
You’ll save big with an Expedia travel package. Combine your airfares, rental cars and hotels and score fantastic discounts. Hotels aren’t your only choice, though. Book with us and take your pick of island resorts, mountain cabins and even castles and houseboats!
Can I choose my airline with a Caroline Expedia holiday package?
You can. We offer more than 550 partner airlines across the globe, so pick the carrier that’s a good fit for your budget and travel needs.
If I'm not able to travel, can I cancel my Caroline holiday package?
You can cancel your Caroline booking if your travel plans have changed. Whether you’ll incur a penalty or not depends on your hotel, airline or car rental company. It may be possible to change or cancel your booking free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

Popular places to visit

The Villages Market Square

4/5(1 review)

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

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

Things to do

Gypsy Gold Horse Farm Walking Tour

Gypsy Gold Horse Farm Walking Tour

S$39
Per adult
Gypsy Gold Horse Farm Walking Tour
King William, a Gypsy Vanner Horse Stallion

Gypsy Gold Horse Farm Tour

S$72
Per adult
100% of travellers recommend
Gypsy Gold Horse Farm Tour
See all activities in The Villages

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.