Countryside Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Countryside

Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was CA $1,362, price is now CA $852 per person
CA $852
per person
Dec 18 - Dec 23
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8.2/10 Very good! (2,105 reviews)

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was CA $1,740, price is now CA $984 per person
CA $984
per person
Jan 24 - Jan 28
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Orlando (MCO)
8.6/10 Excellent! (572 reviews)
It was great everything was just great.

Reviewed on Nov 13, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was CA $2,354, price is now CA $1,380 per person
CA $1,380
per person
Dec 18 - Dec 23
found 22 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
9.2/10 Wonderful! (1,002 reviews)

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was CA $1,578, price is now CA $929 per person
CA $929
per person
Dec 18 - Dec 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
9/10 Wonderful! (4,064 reviews)
Look better on the pictures!

Reviewed on Nov 13, 2026

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was CA $1,476, price is now CA $871 per person
CA $871
per person
Jan 18 - Jan 22
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Orlando (MCO)
9.6/10 Exceptional! (1,234 reviews)
Very pretty hotel. The room was clean. The parking was easy. Was very cozy.

Reviewed on Nov 12, 2026

Where to stay in Countryside

Find the best Countryside areas and neighborhoods for the activities you enjoy most. Learn more about Countryside
A wooden boardwalk leading to a gazebo over a lake, surrounded by trees with autumn leaves.

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

Countryside Hotel Deals

Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista Orlando FL
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Dec 10 to Dec 11
CA $137
CA $154 total
Dec 10 - Dec 11
includes taxes & fees
9/10 Wonderful! (5,451 reviews)
"Beautiful location. Exceptionally priced. Felt safe in all areas. Laundry provided was a huge help."

Reviewed on Nov 13, 2026

Marriott's Grande Vista
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 CA $159 per night from Dec 13 to Dec 14
CA $159
CA $178 total
Dec 13 - Dec 14
includes taxes & fees
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 CA $247 per night from Dec 7 to Dec 8
CA $247
CA $357 total
Dec 7 - Dec 8
includes taxes & fees
The Grove Resort & Water Park Orlando
See all 54,143 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Countryside vacation package cost?
Our Countryside packages, which begin from just CA $852, are the perfect way to save. Choose your favorite 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 vacation package makes it simple to organize 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 1,000,000 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 neighborhood'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 vacation?
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 organizing 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 vacation package?
Yes — that's the beauty of an Expedia vacation 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 vacation package?
It's impossible to predict what the future holds, so it's comforting to know that you can change or cancel your Countryside vacation 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.

Things to do

Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets (US & Canada)

CA $222
per adult
86% of travellers recommend
Universal Orlando Resort Theme Park Tickets (US & Canada)
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

CA $39
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
"Drawn to Life" presented by Cirque du Soleil and Disney

Drawn to Life presented by Cirque du Soleil and Disney

CA $134
per adult
96% of travellers recommend
Drawn to Life presented by Cirque du Soleil and Disney
See all activities in Kissimmee
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.