Photo by Gregg Yutko

Hotels in Oakland

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Check prices for these dates

Tonight
Jun 7 - Jun 8
Tomorrow
Jun 8 - Jun 9
Next weekend
Jun 13 - Jun 15
In two weeks
Jun 20 - Jun 22

Where to stay in Oakland?

Oakland Manor House
Porch

Oakland Manor House

3.0 star property
$550 nightly
The price is $619
Jun 15 - Jun 16
Total includes taxes and fees
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
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
May
$156
Average price during May is $156
Currently viewing crowd sizes and weather for June.

June

trending_upHigh crowds
High 89°F / low 74°F. Partly sunny.
89°
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June, High crowds, average high temperature 89 degrees Fahrenheit, average low temperature 74 degrees Fahrenheit. Partly sunny.
74°
90°
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July, High crowds, average high temperature 90 degrees Fahrenheit, average low temperature 76 degrees Fahrenheit. Partly sunny.
76°
90°
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August, High crowds, average high temperature 90 degrees Fahrenheit, average low temperature 77 degrees Fahrenheit. Partly sunny.
77°
88°
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September, Moderate crowds, average high temperature 88 degrees Fahrenheit, average low temperature 75 degrees Fahrenheit. Partly sunny.
75°
83°
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October, Moderate crowds, average high temperature 83 degrees Fahrenheit, average low temperature 68 degrees Fahrenheit. Sunny most days.
68°
76°
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November, Low crowds, average high temperature 76 degrees Fahrenheit, average low temperature 61 degrees Fahrenheit. Sunny most days.
61°
73°
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December, Moderate crowds, average high temperature 73 degrees Fahrenheit, average low temperature 56 degrees Fahrenheit. Sunny most days.
56°
69°
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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°
87°
weather_sun
May, Low crowds, average high temperature 87 degrees Fahrenheit, average low temperature 69 degrees Fahrenheit. Sunny most days.
69°
Monthly weather averages (˚F)
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Top landmarks in Winter Garden

Flamingo Crossings Town Center

If you want to give your credit card some exercise, head out to Flamingo Crossings Town Center in Bay Lake.

See properties in Flamingo Crossings Town Center
Flamingo Crossings Town Center

Find out more about Oakland

Find out more about Oakland

What's Oakland Like?

If you're looking for the perfect part of the city to explore, why not consider Oakland? Take time to see the sights like Oakland Nature Preserve while you're here. Bella Collina Golf Club and Resurrection Catholic Church are two places to visit nearby.

Where are the Best Places to Stay in Oakland?

One of the top places to stay in Oakland:

The Oak View Place..

City-center apartment with patio
  • Outdoor pool • Garden

How to Get to Oakland

Flying to:

  • Leesburg, FL (LEE-Leesburg Intl.), 21.4 mi (34.5 km) from Oakland
  • Orlando Intl. Airport (MCO), 21.5 mi (34.6 km) from Oakland
  • Kissimmee, FL (ISM-Kissimmee Gateway), 21.6 mi (34.8 km) from Oakland

Things to See and Do in and around Oakland

Things to See near Oakland:

  • Oakland Nature Preserve (0.6 mi/0.9 km away)
  • Resurrection Catholic Church (2.9 mi/4.6 km away)
  • Plant Street Market (2.6 mi/4.3 km away)
  • Newton Park (3.2 mi/5.1 km away)

Things to Do near Oakland:

  • Bella Collina Golf Club (4.5 mi/7.2 km away)
  • Winter Garden Art Association (2.9 mi/4.7 km away)
  • Garden Theatre (2.9 mi/4.6 km away)
  • Central Florida Railroad Museum (2.9 mi/4.7 km away)
  • Carter Family Bowl (3 mi/4.8 km away)

When Is the Best Time to Visit Winter Garden?