Winter Park Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Winter Park Vacation
When a getaway to the city is calling, answer it with a Winter Park vacation package. The neighborhood of Ivanhoe Village, which is great for dining, bars and pubs and shopping, makes a fantastic base for your adventures. Rollins College, Full Sail University and Altamonte Mall are just a few of the attractions worth exploring during your trip to Winter Park. Stop daydreaming and start adventuring. Check out the many options on Expedia today and put your Winter Park vacation plans in motion!
Top Winter Park Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel
Price was CA $1,480, price is now CA $769 per person
CA $769
per person
Apr 30 - May 3
found 20 hours ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
8.2/10 Very Good! (5,182 reviews)
Clean hotel, kid/ family friendly, staff 💯, different menu at breakfast each day
Reviewed on Mar 18, 2026
Westgate Palace Hotel / Universal / I-Drive
International Drive District
Price was CA $1,988, price is now CA $1,044 per person
CA $1,044
per person
Apr 30 - May 7
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.8/10 Excellent! (1,228 reviews)
Great for a family vacation.
Reviewed on Mar 18, 2026
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
International Drive District
Price was CA $1,576, price is now CA $945 per person
CA $945
per person
May 23 - May 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
7.8/10 Good! (381 reviews)
Pool was in the shade most of the day
Reviewed on Mar 10, 2026
Winter Park Hotel Deals
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr Orlando FL
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Apr 19 to Apr 20
CA $176
CA $198 total
Apr 19 - Apr 20
includes taxes & fees
9.2/10 Wonderful! (4,908 reviews)
Great resort
Reviewed on Mar 19, 2026
Hyatt Regency Orlando International Airport
9300 Jeff Fuqua Boulevard Orlando FL
Fully refundableReserve now, pay when you stay
The price is CA $273 per night from Mar 23 to Mar 24
CA $273
CA $308 total
Mar 23 - Mar 24
includes taxes & fees
9.4/10 Exceptional! (4,049 reviews)
Very nice and so convenient to fly out the next am
Reviewed on Mar 18, 2026
Universal's Cabana Bay Beach Resort
6550 Adventure Way Orlando FL
Fully refundableReserve now, pay when you stay
The price is CA $224 per night from Apr 12 to Apr 13
CA $224
CA $252 total
Apr 12 - Apr 13
includes taxes & fees
9/10 Wonderful! (6,457 reviews)
Great
Reviewed on Mar 18, 2026
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.
Discover the most popular places to visit in Winter Park
Walt Disney World® Resort
4.5/5(226 reviews)
Walt Disney World® Resort is part of Orlando. It makes up part of bustling metropolis that is home to 240,000 inhabitants. Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando’s city center. If you are flying in, Walt Disney World® Resort is approximately 15 miles (24 kilometers) from Orlando International Airport.
Universal Studios Florida
4.5/5(988 reviews)
Movie sets and thrill rides combine to create this internationally acclaimed theme park.
Universal Orlando Resort
4.5/5(399 reviews)
Make your Florida vacation one to remember with a stay at this hotel and theme park complex.
What to do in Winter Park
Universal Orlando Resort Theme Park Tickets (US & Canada)
CA $237
per adult
86% of travellers recommend
Explore a world of travel with Expedia
- 4 Star Hotels in Baldwin Park
- Hotels near AdventHealth Orlando
- Hyatt Hotels in Aloma
- Spa Hotels in Aloma
- Aloma Hotels
- Audubon Park Hotels
- Hotels with Balconies in Baldwin Park
- Starwood Capital Hotels in Baldwin Park
- Baldwin Park Hotels
- Hotels near Casa Feliz Historic Home Museum
- Hotels near Crealde School of Art
- Hotels near Full Sail University
- Hotels near Harry P. Leu Gardens
- Hotels near Lee Road Shopping Center
- Aparthotels in Maitland
- B&B in Maitland
- Cabin Rentals in Maitland
- Castles in Maitland
- Guest Houses in Maitland
- Holiday Park Resorts in Maitland
- Boutique Hotels in Maitland
- Cheap Hotels in Maitland
- Diamond Resorts in Maitland
- Hotels with Hot Tubs in Maitland
- Pet-Friendly Hotels in Maitland
- Shopping Hotels in Maitland
- Wyndham Hotels in Maitland
- Maitland Hotels
- Inns in Maitland
- Lodges in Maitland
- Motels in Maitland
- Resorts in Maitland
- Cheap Hotels in North Orange
- Pet-Friendly Hotels in North Orange
- Waterpark Hotels in North Orange
- North Orange Hotels
- Universal Orlando Resort in Orlando
- Walt Disney World Resort in Orlando
- Orlando Hotels
- Hotels near Orlando Museum of Art
- Resorts in Orlando
- Hotels near Orlando Science Center
- Lgbt Friendly Hotels in Orwin Manor
- Hotels near Rollins College
- Hotels near The Center of Winter Park Shopping Center
- Hotels near Village Plaza Shopping Center
- Hotels near Walt Disney World® Resort
- Hotels near Winter Park Country Club
- Guest Houses in Winter Park Station
- Hotels near Winter Park Station
- Hotels near Winter Park Tennis Center
- Hotels near Winter Park Village
- Flights to Orlando
- Flights from Maitland
- Flights from Buffalo (BUF) to Orlando (MCO)
- Flights from Detroit (DTW) to Orlando (MCO)
- Flights from Ottawa (YOW) to Orlando (MCO)
- Flights from Montreal (YUL) to Orlando (MCO)
- Flights from Vancouver (YVR) to Orlando (MCO)
- Flights from Toronto (YYZ) to Orlando (MCO)
- Adventhealth Orlando
- Albin Polasek Museum and Sculpture Gardens
- Casa Feliz Historic Home Museum
- Cathedral Church of St. Luke
- Church Street Station
- City Arts Factory
- Downtown Orlando Vacations
- Dr. Phillips Center for the Performing Arts
- Harry P. Leu Gardens
- Kia Center
- Kraft Azalea Gardens
- Lake Eola Park
- Lake Virginia
- Loch Haven Park
- Mad Cow Theatre
- Visit Maitland
- Mead Garden
- Orange Avenue
- Orange County Regional History Center
- Visit Aloma
- Orlando Museum of Art
- Visit Orwin Manor
- Orlando Science Center
- Orlando Vacations
- Princeton Park
- Red Bug Lake Park
- Rollins Museum of Art
- St. James Cathedral
- The Plaza Theatre
- Village Plaza Shopping Center
- Walt Disney World® Resort
- Winter Pines Golf Club
- Zora Neale Hurston National Museum of Fine Arts
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
