Vacations Close To Winter Park Village

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Winter Park Village Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Meliá Orlando Celebration

Meliá Orlando Celebration

4 out of 5
Price was $1,156, price is now $838 per person
$838
per person
Dec 28 - Jan 2
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was $5,038, price is now $2,711 per person
$2,711
per person
Dec 28 - Jan 2
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $1,506, price is now $868 per person
$868
per person
Dec 28 - Jan 2
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $1,430, price is now $862 per person
$862
per person
Dec 28 - Jan 2
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
front desk lady was rude

Reviewed on Nov 2, 2026

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Save 100% on your flight
Price was $1,673, price is now $1,121 per person
$1,121
per person
Dec 28 - Jan 2
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Rooms are clean,spacious. My absolute favorite place to stay when I’m in Orlando, Fl

Reviewed on Nov 2, 2026

Omni Orlando Resort at ChampionsGate

Omni Orlando Resort at ChampionsGate

4 out of 5
Champions Gate
Price was $1,270, price is now $939 per person
$939
per person
Dec 28 - Jan 2
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)

Calypso Cay Vacation Villas

Calypso Cay Vacation Villas

3.5 out of 5
Price was $1,252, price is now $929 per person
$929
per person
Dec 28 - Jan 2
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Clean room, amenities are great multiple pools and hot tubs, the room I had 3 bedroom definitely had plenty of room for the family.

Reviewed on Nov 2, 2026

Floridays Resort Orlando

Floridays Resort Orlando

4 out of 5
International Drive District
Price was $1,509, price is now $1,145 per person
$1,145
per person
Dec 28 - Jan 2
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Great stay

Reviewed on Nov 1, 2026

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Best Lodging Options Near Winter Park Village

The Alfond Inn

The Alfond Inn

4 out of 5
300 East New England Avenue Winter Park FL
3.25 km from Winter Park Village
Book a stay at this luxury hotel in Winter Park. Enjoy free WiFi, 2 outdoor pools, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
Park Plaza Hotel

Park Plaza Hotel

3 out of 5
307 South Park Avenue  Winter Park FL
3.44 km from Winter Park Village
Book a stay at this golf hotel in Winter Park. Enjoy free WiFi, room service, and valet parking (surcharge). Our guests praise the helpful staff in our reviews. ...
SpringHill Suites by Marriott Winter Park

SpringHill Suites by Marriott Winter Park

2.5 out of 5
1127 NORTH ORLANDO AVENUE Winter Park FL
3.48 km from Winter Park Village
Book a stay at this business-friendly hotel in Winter Park. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in our ...
Days Inn by Wyndham N Orlando/Casselberry

Days Inn by Wyndham N Orlando/Casselberry

2 out of 5
8245 South US Hwy 17/92 Fern Park FL
3.44 km from Winter Park Village
Book a stay at this business-friendly motel in Fern Park. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. ...
Hilton Garden Inn Winter Park

Hilton Garden Inn Winter Park

3 out of 5
1275 Lee Road Winter Park FL
3.68 km from Winter Park Village
Book a stay at this business-friendly hotel in Winter Park. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff ...
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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.