Countryside Vacation Packages

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Top Holiday Package Deals in Countryside

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was CA $1,145, price is now CA $629 per person
CA $629
per person
Nov 2 - Nov 8
found 5 hours ago
Roundtrip flight included
Montreal (YUL) to Orlando (MCO)
8/10 Very Good! (1,346 reviews)
First off the front desk needs retraining they gave us the completly incorrect room. Second the correct room the ceiling leaked. Third room was not properly cleaned the pull out sofa had visible crumbs and the ac unit was inoperable. The final upgraded room was extremely excellent.

Reviewed on Sep. 1, 2025

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was CA $1,953, price is now CA $700 per person
CA $700
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8.2/10 Very Good! (5,167 reviews)
Nice to stay with family and breakfast was perfect

Reviewed on Sep. 1, 2025

ette hotel

ette hotel

5 out of 5
Price was CA $2,797, price is now CA $1,434 per person
CA $1,434
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
9.8/10 Exceptional! (330 reviews)
Excellent service, food, location and staff! Thank you

Reviewed on Aug. 11, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $1,539, price is now CA $792 per person
CA $792
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Orlando (MCO)
8.2/10 Very Good! (5,275 reviews)
Overall we had a nice visit. Ventilation was weird, smelling “things” from other units in the bathrooms. The adult pool allowed kids, employees couldn’t explain how to get to it and there was no employees there or bar. The Drafts restaurant was really nice, check in staff was awesome. Requests were responded to immediately

Reviewed on Sep. 1, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was CA $1,293, price is now CA $726 per person
CA $726
per person
Oct 10 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.8/10 Excellent! (1,008 reviews)
Being able to text the front desk for my needs was very helpful! Staff was friendly and the Universal shuttles were convenient.

Reviewed on Aug. 30, 2025

Where to stay in Countryside

Find the best Countryside areas and neighborhoods for the activities you enjoy most. Learn more about Countryside
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Reunion

1 out of top 10 points of interest in this area

The waterparks and pristine golf courses are top of the list for many visitors to Reunion. A stop by Reunion Resort Golf Course or Jack Nicklaus Course might round out your trip.

Find hotels in Reunion

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 $120 per night from Sep 22 to Sep 23
CA $120
CA $135 total
Sep 22 - Sep 23
includes taxes & fees
Marriott's Grande Vista
Holiday Inn Resort Kissimmee by the Parks by IHG

Holiday Inn Resort Kissimmee by the Parks by IHG

3.5 out of 5
3011 Maingate Ln, Kissimmee, FL
Fully refundable
The price is CA $76 per night from Sep 4 to Sep 5
CA $76
CA $113 total
Sep 4 - Sep 5
includes taxes & fees
Holiday Inn Resort Kissimmee by the Parks by IHG
Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

3 out of 5
9000 International Drive, Orlando, FL
Fully refundableReserve now, pay when you stay
The price is CA $93 per night from Sep 7 to Sep 8
CA $93
CA $105 total
Sep 7 - Sep 8
includes taxes & fees
Rosen Inn at Pointe Orlando
See all 51,200 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 $629, 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

Old Town

Old Town

4/5(270 reviews)

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
Orlando showing golf

Mystic Dunes Golf Club

2.5/5(2 reviews)

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

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 lively festivals in this family-friendly area.

Kissimmee Lakefront Park

Things to do

Florida: 90 Minute Everglades Cruise

Florida: 90 Minute Everglades Cruise

CA $69
per adult
100% of travellers recommend
Florida: 90 Minute Everglades Cruise
Orlando: Polynesian Fire Luau with Dinner and Live Show

Orlando: Polynesian Fire Luau with Dinner and Live Show

CA $103
per adult
80% of travellers recommend
Orlando: Polynesian Fire Luau with Dinner and Live Show
Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner

Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner

CA $21
per adult
Kissimmee: Old Town Ferris Wheel, Attractions, and Dinner
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.