Photo by Gregg Yutko

Hotels in Oakland

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Check prices for these dates

Tonight
May 7 - May 8
Tomorrow
May 8 - May 9
This weekend
May 9 - May 11
Next weekend
May 16 - May 18

Where to stay in Oakland?

Oakland Manor House
Porch

Oakland Manor House

2.0 star property
The price is $703
includes taxes & fees
$625 per night
May 11 - May 12
Oakland Manor House
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.
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Our prices for hotels in Winter Garden are cheapest in September

See average prices and weather for all months

Price trends for hotels in Winter Garden

Pricing is based on two traveler single night rates
May
$156
Average price during May is $156
Jun
$163
Average price during June is $163
Jul
$158
Average price during July is $158
Aug
$153
Average price during August is $153
Sep
$148
Average price during September is $148
Oct
$158
Average price during October is $158
Nov
$166
Average price during November is $166
Dec
$254
Average price during December is $254
Jan
$179
Average price during January is $179
Feb
$196
Average price during February is $196
Mar
$188
Average price during March is $188
Apr
$177
Average price during April is $177
Currently viewing crowd sizes and weather for May.

May

trending_downLow crowds
High 87°F / low 69°F. Sunny most days.
87°
weather_sun
May, Low crowds, average high temperature 87 degrees Fahrenheit, average low temperature 69 degrees Fahrenheit. Sunny most days.
69°
89°
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June, High crowds, average high temperature 89 degrees Fahrenheit, average low temperature 74 degrees Fahrenheit. Partly sunny.
74°
90°
weather_partly_sunny
July, High crowds, average high temperature 90 degrees Fahrenheit, average low temperature 76 degrees Fahrenheit. Partly sunny.
76°
90°
weather_partly_sunny
August, High crowds, average high temperature 90 degrees Fahrenheit, average low temperature 77 degrees Fahrenheit. Partly sunny.
77°
88°
weather_partly_sunny
September, Moderate crowds, average high temperature 88 degrees Fahrenheit, average low temperature 75 degrees Fahrenheit. Partly sunny.
75°
83°
weather_sun
October, Moderate crowds, average high temperature 83 degrees Fahrenheit, average low temperature 68 degrees Fahrenheit. Sunny most days.
68°
76°
weather_sun
November, Low crowds, average high temperature 76 degrees Fahrenheit, average low temperature 61 degrees Fahrenheit. Sunny most days.
61°
73°
weather_sun
December, Moderate crowds, average high temperature 73 degrees Fahrenheit, average low temperature 56 degrees Fahrenheit. Sunny most days.
56°
69°
weather_sun
January, Low crowds, average high temperature 69 degrees Fahrenheit, average low temperature 52 degrees Fahrenheit. Sunny most days.
52°
73°
weather_sun
February, Low crowds, average high temperature 73 degrees Fahrenheit, average low temperature 56 degrees Fahrenheit. Sunny most days.
56°
78°
weather_sun
March, High crowds, average high temperature 78 degrees Fahrenheit, average low temperature 59 degrees Fahrenheit. Sunny most days.
59°
82°
weather_sun
April, Moderate crowds, average high temperature 82 degrees Fahrenheit, average low temperature 64 degrees Fahrenheit. Sunny most days.
64°
Monthly weather averages (˚F)
View all properties

Top landmarks in Winter Garden

Disney's Magnolia Golf Course

You might want to play some rounds at Disney's Magnolia Golf Course, located 11.1 mi (17.9 km) from central Winter Garden. If Disney's Magnolia Golf Course doesn't quite scratch your golfing itch, Orange Lake Golf, and Grand Cypress Golf Club are also nearby.

See properties in Disney's Magnolia Golf Course
Disney's Magnolia Golf Course
A tranquil hotel pool encircled by beautiful arches, enhancing the ambiance for leisure and relaxation.

Summer Getaway Sale

Save 25% or more on select hotels, and earn 50% more rewards on all properties. Book by May 26 and travel by Sep 30, 2025. See terms*
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Terms and conditions

*Book by 5/26/2025 11:59 pm in hotel property local time. Stay between 4/17/2025-9/30/2025. Member Prices are available to Hotels.com® app users and One Key members. Limited availability, blackout periods may apply.

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