Countryside Holidays

Book a Hotel + Flight or Car together to unlock savings

Where to stay in Countryside

Find the best Countryside areas and neighborhoods for the activities you enjoy most. Learn more about Countryside
Beautiful morning on Lale Tohopekaliga in Kissimmee, Florida during fall, Florida, Kissimmee, lake, autumn

Cumbrian Lakes

While there might not be top attractions in Cumbrian Lakes, you can explore the larger area and discover places like Give Kids the World Village and Old Town.

Find hotels in Cumbrian Lakes

Top hotels in Countryside

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4 out of 5
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
The price is 3.926.448 ₫ per night from 1 Jun to 2 Jun
3.926.448 ₫
4.417.386 ₫ total
1 Jun - 2 Jun
includes taxes & fees
9.2/10 Wonderful! (5,479 reviews)
This was our third year staying at this resort. Always clean and welcoming. This year after our 18 hour drive upon check in, we were informed of a $350 parking fee for our 10 day stay! Beware! Hidden of hidden parking fee unless your become a timeshare member. Will not be returning ever again!

Reviewed on 15 May 2026

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

4 out of 5
14501 Grove Resort Avenue Winter Garden FL
Fully refundableReserve now, pay when you stay
The price is 4.348.080 ₫ per night from 21 May to 22 May
4.348.080 ₫
6.344.244 ₫ total
21 May - 22 May
includes taxes & fees
8/10 Very Good! (9,861 reviews)
The crazy river is closed for update 😏

Reviewed on 15 May 2026

The Grove Resort & Water Park Orlando
DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel

3 out of 5
7400 Canada Ave Orlando FL
Fully refundable
The price is 2.268.117 ₫ per night from 21 May to 22 May
2.268.117 ₫
2.551.401 ₫ total
21 May - 22 May
includes taxes & fees
8.6/10 Excellent! (1,376 reviews)
The pool was so nice and relaxing the breakfast was delicious and the rooms are so nice and roomy ,the staff was very friendly and welcoming! I would definitely stay again when visiting Orlando .

Reviewed on 15 May 2026

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
See all 51,492 properties in Countryside
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 Countryside holiday package cost?
Our Countryside packages, which begin from just , are the perfect way to save. Choose your favourite flights, hotels and rental cars to create a custom-built escape.
How do I get a cheap travel package to Countryside?
Combining your flight and hotel with Expedia won't just save valuable time — it'll save you a pretty penny too. A Countryside holiday package makes it simple to organise the ideal trip. With more than 550 airlines across the world to pick from, finding flights that suit your busy schedule won't be a challenge. In addition to that, we've got over 1null000null000 hotel options globally to choose from. Now that's choice! Whatever your budget, Expedia brings the world within your reach.
Where should I stay in Countryside?
Book a hotel nice and close to ChampionsGate Golf Club, one of this neighbourhood's most popular attractions. It's the ideal spot if you're looking to capture some great travel photos.
How far in advance should I book my Countryside holiday?
Reserving your flight early with Expedia means one less thing to have to worry about. Many air carriers advertise prices up to 12 months in advance. This is typically the cheapest time to book. If circumstances have left you booking late, fantastic last-minute deals to Countryside sometimes become available in the weeks leading up to departure.
What does an Expedia Countryside travel package include?
Flights, hotels and car rentals — we connect you to the best deals. All you'll have to do is decide on your preferred combination. Once you've made your booking, you can add on the exciting stuff like experiences and tours. Our travel packages make it simple to customize an amazing Countryside trip.
What should I know before booking a Countryside travel package?
When you book your flights, hotels and car rentals together, you'll be rewarded with great discounts. Whether you're organising an outdoor getaway in a chalet or prefer to stay in a convenient hotel in the city, Expedia can help make it happen.
Can I choose my airline with a Countryside Expedia holiday package?
Yes — that's the beauty of an Expedia holiday package. You're in control. We have more than 550 airline partners across the globe, so you have options galore when arranging your Countryside escape.
If I'm not able to travel, can I cancel my Countryside holiday package?
It's impossible to predict what the future holds, so it's comforting to know that you can change or cancel your Countryside holiday package. If you made your booking in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal to learn more.

Popular places to visit

EyeEm Custom Shoots Q4 2018

Old Town

Enjoy the rides and games at Old Town and see why people love this theme park in Kissimmee. Visit the shops and top-notch restaurants in this family-friendly area.

Old Town
Mystic Dunes Golf Club

Mystic Dunes Golf Club

Enjoy a round of golf in Four Corners at Mystic Dunes Golf Club. Stroll along the lakeside or experience the entertainment choices in this family-friendly area.

Mystic Dunes Golf Club
Kissimmee Lakefront Park Grassy waterfront park with walking paths, a fishing pier, picnic pavilions, and a shaded playground. children's playgrounds, splash pad

Kissimmee Lakefront Park

Kissimmee Lakefront Park is just one of the places to see in Kissimmee, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or experience the entertainment choices in this family-friendly area.

Kissimmee Lakefront Park