Downtown Winter Garden Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Photo by Shannon Maya
Downtown Winter Garden Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham St Augustine/Historic Downtown
Uptown
per person
Sep 15 - Sep 19
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Stay at this hotel in St. Augustine. Enjoy free WiFi, a free area shuttle, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Castillo de San Marcos National Monument and St. George Street are located nearby.
The Kenwood Inn
St. Augustine Historic District
Save 100% on your flight
per person
Sep 15 - Sep 19
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Stay at this 3.5-star B&B in St. Augustine. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions St. Augustine Beach and St. George Street are located nearby.
Casa Monica Resort & Spa, Autograph Collection
St. Augustine Historic District
Save 100% on your flight
per person
Sep 15 - Sep 19
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Stay at this 4-star luxury hotel in St. Augustine. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions St. Augustine Beach and St. George Street are located nearby.
Hilton Garden Inn Jacksonville Ponte Vedra Sawgrass
Palm Valley
per person
Oct 5 - Oct 9
just found
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Stay at this 3-star business-friendly hotel in Ponte Vedra Beach. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions TPC Sawgrass and Jacksonville Beach Pier are located nearby.
Old City House Inn and Restaurant
St. Augustine Historic District
Save 100% on your flight
per person
Sep 15 - Sep 19
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Stay at this 3.5-star historic B&B in St. Augustine. Enjoy free breakfast, free WiFi, and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions St. Augustine Beach and St. George Street are located nearby.
St George Inn
St. Augustine Historic District
Save 100% on your flight
per person
Sep 15 - Sep 19
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Stay at this 3.5-star hotel in St. Augustine. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff in our reviews. Popular attractions St. Augustine Beach and Castillo de San Marcos National Monument are located nearby.
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See all available trips from Columbus to Downtown Winter Garden
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DoubleTree by Hilton at the Entrance to Universal Orlando
5780 Major Blvd, Orlando, FL
15.93 km from Downtown Winter Garden
Stay at this 4-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the pool and the helpful staff in ...
Marriott's Grande Vista
5925 Avenida Vista, Orlando, FL
22.81 km from Downtown Winter Garden
Stay at this 4-star spa hotel in Orlando. Enjoy free WiFi, 4 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. ...
Rosen Inn at Pointe Orlando
9000 International Drive, Orlando, FL
18.41 km from Downtown Winter Garden
Stay at this 3-star family-friendly hotel in Orlando. Enjoy free WiFi, 3 outdoor pools, and 2 coffee shops/cafes. Our guests praise the pool and the helpful ...
Kompose Boutique Resort at Theme Parks
7491 W Irlo Bronson Memorial Hwy, Kissimmee, FL
25.66 km from Downtown Winter Garden
Stay at this 4-star business-friendly resort in Kissimmee. Enjoy free breakfast, free WiFi, and 2 hot tubs. Popular attractions Disney's Animal Kingdom® Theme ...
Universal's Cabana Bay Beach Resort
6550 Adventure Way, Orlando, FL
15.64 km from Downtown Winter Garden
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Home2 Suites by Hilton Orlando at Flamingo Crossings
341 Flagler Ave, Winter Garden, FL
20.53 km from Downtown Winter Garden
Stay at this 3-star business-friendly hotel in Winter Garden. Enjoy free breakfast, a free theme park shuttle, and a 24-hour fitness center. Our guests praise ...
Holiday Inn Resort Orlando Suites - Waterpark by IHG
14500 Continental Gateway, Orlando, FL
24.34 km from Downtown Winter Garden
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy 2 outdoor pools, 5 restaurants, and 2 hot tubs. Our guests praise the clean rooms and the family ...
The Grove Resort & Water Park Orlando
14501 Grove Resort Avenue, Winter Garden, FL
23.65 km from Downtown Winter Garden
Stay at this 4-star family-friendly resort in Four Corners. Enjoy 6 outdoor pools, 3 restaurants, and 2 hot tubs. Our guests praise the pool and the helpful ...
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
8800 Vistana Centre Dr, Orlando, FL
23.33 km from Downtown Winter Garden
Stay at this 4-star eco-certified hotel in Orlando. Enjoy free WiFi, 6 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in ...
DoubleTree by Hilton Hotel Orlando Downtown
60 South Ivanhoe Boulevard, Orlando, FL
20.31 km from Downtown Winter Garden
Book a stay at this business-friendly hotel in Orlando. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and ...
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
631 FLAGLER AVE, Winter Garden, FL
20.63 km from Downtown Winter Garden
Book a stay at this business-friendly hotel in Winter Garden. Enjoy free breakfast, free WiFi, and a free theme park shuttle. Our guests praise the breakfast ...
CoCo Key Hotel and Water Resort
7400 International Dr, Orlando, FL
16.72 km from Downtown Winter Garden
Stay at this 3.5-star family-friendly hotel in Orlando. Enjoy 3 outdoor pools, 4 restaurants, and 2 poolside bars. Our guests praise the pool and the helpful ...
Westgate Lakes Resort & Spa Universal Studios Area
9500 Turkey Lake Rd, Orlando, FL
18.68 km from Downtown Winter Garden
Stay at this 4-star spa hotel in Orlando. Enjoy free parking, 7 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
Don't see what you're looking for?
See all available properties in Downtown Winter Garden
View all propertiesLowest 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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Fri, Sep 12 - Sun, Sep 21
DTW
Detroit Metropolitan Wayne County
MCO
Orlando Intl.
$90 Roundtrip, found 6 days ago
$90
Roundtrip
found 6 days ago
Sun, Oct 5 - Tue, Oct 7
LGA
LaGuardia
MCO
Orlando Intl.
$100 Roundtrip, found 3 hours ago
$100
Roundtrip
found 3 hours ago
Fri, Sep 5 - Sun, Sep 7
SWF
Stewart Intl.
MCO
Orlando Intl.
$125 Roundtrip, found 4 days ago
$125
Roundtrip
found 4 days ago
Sat, Nov 1 - Wed, Nov 5
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$137 Roundtrip, found 4 days ago
$137
Roundtrip
found 4 days ago
Sun, Sep 14 - Fri, Sep 26
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$139 Roundtrip, found 6 days ago
$139
Roundtrip
found 6 days ago
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