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.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was CA $1,029, price is now CA $607 per person
CA $607
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very Good! (5,138 reviews)
Great place to stay. Very clean, nice pool, great location, and tasty breakfast.

Reviewed on May 13, 2026

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was CA $1,550, price is now CA $809 per person
CA $809
per person
Jul 2 - Jul 9
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very Good! (1,893 reviews)
Excelente volvería a ir miles de veces

Reviewed on May 11, 2026

Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Price was CA $1,489, price is now CA $786 per person
CA $786
per person
Jul 2 - Jul 9
found 19 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (1,021 reviews)
I stayed at one of the newly refurbished rooms. The room was spotless and the bed was very comfortable. What needs refurbishment is the carpeting in the lobbies. They have seen better days. The front desk personel were courteous. The only reason I would not go back is due to the awful traffic on Irlo Bronson Rd.

Reviewed on May 12, 2026

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was CA $1,354, price is now CA $721 per person
CA $721
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very Good! (1,680 reviews)
Always a pleasure to stay

Reviewed on May 14, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $1,890, price is now CA $1,082 per person
CA $1,082
per person
Jul 17 - Jul 24
found 2 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8.4/10 Very Good! (6,342 reviews)
Clean and convenient

Reviewed on May 14, 2026

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

Countryside Hotel Deals

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
The price is CA $163 per night from Jun 8 to Jun 9
CA $163
CA $184 total
Jun 8 - Jun 9
includes taxes & fees
9.2/10 Wonderful! (5,465 reviews)
I was impressed with the property. The townhouse was more than I expected. I assumed I was getting a 2 bedroom condo type accommodation. It had 2 stories and the 2 twins were upstairs. The kitchen was spacious. Although I didn’t use much of the utensils or kitchenware it had just about everything ...

Reviewed on May 14, 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 CA $226 per night from May 21 to May 22
CA $226
CA $330 total
May 21 - May 22
includes taxes & fees
8/10 Very Good! (9,850 reviews)
Nice property

Reviewed on May 14, 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 CA $124 per night from May 21 to May 22
CA $124
CA $139 total
May 21 - May 22
includes taxes & fees
8.6/10 Excellent! (1,368 reviews)
well organized hotel and the layout of the rooms were well thought out. Location in relation to International drive was very good

Reviewed on May 14, 2026

DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel
See all 51,420 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
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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 $607, 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.

Discover the most popular places to visit in Countryside

EyeEm Custom Shoots Q4 2018

Old Town

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

Old Town
Mystic Dunes Golf Club

Mystic Dunes Golf Club

Tee off at one of Orlando’s premier golf clubs and enjoy the championship course, the excellent facilities and the laid-back Florida vibe.

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

Things to do

Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets (US & Canada)

CA $221
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 $38
per adult
92% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

CA $53
per traveller
86% of travellers recommend
LEGOLAND® Florida Tickets
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.