Countryside Vacations from $291

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 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

The Latest Countryside Vacation Packages

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

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $589, price is now $291 per person
$291
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8/10 Very Good! (1,360 reviews)
The place is huge, and they have everything. The room was clean and everyone was so kind.

Reviewed on Sep 23, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was $835, price is now $353 per person
$353
per person
Dec 10 - Dec 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (5,346 reviews)
Room was leaking water

Reviewed on Sep 30, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $756, price is now $345 per person
$345
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (1,012 reviews)
clean and beautiful

Reviewed on Sep 26, 2025

Westgate River Ranch Resort & Rodeo

Westgate River Ranch Resort & Rodeo

3.5 out of 5
Price was $922, price is now $448 per person
$448
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (386 reviews)
The hotel was good but now with the water park and other amenities it’s even better. My grandkids loved it, it was s great experience for them and something very different to other hotels in Fl

Reviewed on Sep 16, 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was $946, price is now $464 per person
$464
per person
Dec 10 - Dec 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.6/10 Exceptional! (1,003 reviews)
As always my stay was great. The staff was also amazing.

Reviewed on Sep 25, 2025

Where to stay in Countryside

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

Windsor Hills

4.5/5(6 area reviews)

If you're looking for some top things to see and do in Windsor Hills and surrounding area, you can visit Mystic Dunes Golf Club and Island H2O Live!.

Find hotels in Windsor Hills

Countryside Hotel Deals

Marriott's Grande Vista

Marriott's Grande Vista

4 out of 5
5925 Avenida Vista, Orlando, FL
$87 nightly
The price is $98 total per night from Oct 26 to Oct 27
$98 total
Oct 26 - Oct 27
Total with taxes and fees
8.8/10 Excellent! (3,253 reviews)
"Perfect families. Close to a Publix and sea world. Spacious and clean"

Reviewed on Oct 1, 2025

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
$99 nightly
The price is $112 total per night from Oct 27 to Oct 28
$112 total
Oct 27 - Oct 28
Total with taxes and fees
9.2/10 Wonderful! (3,595 reviews)
"Cannot say enough, good things about this spot!"

Reviewed on Oct 1, 2025

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
DoubleTree by Hilton Hotel Orlando at SeaWorld

DoubleTree by Hilton Hotel Orlando at SeaWorld

4 out of 5
10100 International Drive, Orlando, FL
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $104 total per night from Oct 9 to Oct 10
$104 total
Oct 9 - Oct 10
Total with taxes and fees
7.4/10 Good! (6,155 reviews)
"This hotel is perfectly located and gives access to Orlando."

Reviewed on Sep 25, 2025

DoubleTree by Hilton Hotel Orlando at SeaWorld
See all 51,876 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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Countryside

caught in a torrential downpour while exploring Old Town but did get to see lots of the awesome classic cars that come out for the weekly Friday night car show - a busy tourist spot but a nice change from the neighboring Disney/Sea World/Universal parks

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
Orlando which includes golf

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

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

LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

$79
per traveler
84% of travellers recommend
LEGOLAND® Florida Tickets
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options

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

$32
per adult
90% of travellers recommend
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
Universal Orlando Resort Express Passes

Universal Orlando Resort Express Passes

$160
per traveler
84% of travellers recommend
Universal Orlando Resort Express Passes
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.