Photo by Gregg Yutko

Oakland Hotels near Winter Garden

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Top Trending Hotels Near Oakland, Winter Garden

The Delaney Hotel

3.5 star property
9.6 out of 10, Exceptional, (1006)
"Excellent all around place and stay "
The Delaney Hotel

Lakeside Inn

3.0 star property
8.8 out of 10, Excellent, (1202)
"Lovely location and quiet peaceful stay"
Lakeside Inn

The Eo Inn - Downtown

3.0 star property
8.0 out of 10, Very Good, (1004)
"Good hotel "
The price is P4,972
P5,594 total
includes taxes & fees
Aug 5 - Aug 6
The Eo Inn - Downtown

Holiday Inn Express And Suites Clermont Se West Orlando by IHG

2.5 star property
8.2 out of 10, Very Good, (770)
"The amenities from the resort were AMAZING ! "
The price is P4,390
P4,873 total
includes taxes & fees
Aug 24 - Aug 25
Holiday Inn Express And Suites Clermont Se West Orlando by IHG

The Grove Resort & Water Park Orlando

4.0 star property
8.0 out of 10, Very Good, (8252)
"Perfect stay for families! "
The price is P8,666
P12,367 total
includes taxes & fees
Aug 5 - Aug 6
The Grove Resort & Water Park Orlando

DoubleTree by Hilton at the Entrance to Universal Orlando

4.0 star property
8.4 out of 10, Very Good, (6508)
"Great location, great price, friendly staff, good accommodations on site."
The price is P5,389
P6,063 total
includes taxes & fees
Aug 14 - Aug 15
DoubleTree by Hilton at the Entrance to Universal Orlando

SPOT X Hotel Orlando/Intl Dr by The Red Collection

3.0 star property
8.6 out of 10, Excellent, (2659)
"Enjoyed my stay nice place. "
The price is P4,153
P4,672 total
includes taxes & fees
Aug 10 - Aug 11
SPOT X Hotel Orlando/Intl Dr by The Red Collection

Avanti International Resort

4.0 star property
7.8 out of 10, Good, (4026)
"great resort will stay there again"
Avanti International Resort

Holiday Inn Resort Orlando Suites - Waterpark by IHG

3.5 star property
7.0 out of 10, Good, (3865)
"To spend the weekend with the kids is a perfect place, food, entertainment and the water park, can’t go wrong"
The price is P3,781
P8,507 total
includes taxes & fees
Aug 24 - Aug 25
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Hyatt Regency Orlando

4.5 star property
9.2 out of 10, Wonderful, (1688)
"Great hotel. "
The price is P8,666
P12,988 total
includes taxes & fees
Aug 5 - Aug 6
Hyatt Regency Orlando

Hyatt Regency Grand Cypress

4.0 star property
9.2 out of 10, Wonderful, (2212)
"Amazing place to stay "
The price is P8,317
P12,629 total
includes taxes & fees
Aug 13 - Aug 14
Hyatt Regency Grand Cypress

Rosen Inn International

3.0 star property
8.4 out of 10, Very Good, (5723)
"Best stay I've ever been in"
The price is P4,420
P4,972 total
includes taxes & fees
Aug 17 - Aug 18
Rosen Inn International

Rosen Inn Lake Buena Vista

3.5 star property
8.6 out of 10, Excellent, (5354)
"Amazing location and staff were very accommodating."
The price is P4,420
P4,972 total
includes taxes & fees
Aug 10 - Aug 11
Rosen Inn Lake Buena Vista

Rosen Shingle Creek

4.5 star property
9.4 out of 10, Exceptional, (3946)
"Great place to stay "
The price is P6,933
P7,800 total
includes taxes & fees
Aug 31 - Sep 1
Rosen Shingle Creek

Caribe Royale Orlando

4.5 star property
9.2 out of 10, Wonderful, (4312)
"Great stay - close to many attractions. "
The price is P9,248
P12,891 total
includes taxes & fees
Aug 31 - Sep 1
Caribe Royale Orlando

Wyndham Garden Orlando Airport

3.0 star property
9.0 out of 10, Wonderful, (3769)
"Great stay"
The price is P5,043
P5,673 total
includes taxes & fees
Aug 5 - Aug 6
Wyndham Garden Orlando Airport

The Alfond Inn

4.0 star property
9.4 out of 10, Exceptional, (1007)
"The hotel staff, restaurants and accommodations are very nice."
The Alfond Inn

Hotel SonoHotel IDrive District

3.0 star property
7.2 out of 10, Good, (2850)
"Lovely staff and rooms!"
Hotel SonoHotel IDrive District

Holiday Inn Club Vacations at Orange Lake Resort by IHG

4.0 star property
8.6 out of 10, Excellent, (2266)
"Excellent resort."
The price is P5,883
P9,178 total
includes taxes & fees
Aug 18 - Aug 19
Holiday Inn Club Vacations at Orange Lake Resort by IHG

La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks

3.0 star property
8.6 out of 10, Excellent, (2148)
"The hotel was very clean and nice!!"
The price is P5,444
P6,125 total
includes taxes & fees
Aug 5 - Aug 6
La Quinta Inn & Suites by Wyndham Orlando - IDrive Theme Parks
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.
Save an average of 15% on thousands of hotels when you're signed in

Where to stay in Oakland

Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Learn more about Oakland
Vista del Lago map

Vista del Lago

While Vista del Lago isn't home to many top sights, Orange Lake Golf and Island H2O Live! are some notable places to visit nearby.

Downtown Winter Garden map

Downtown Winter Garden

While visiting Downtown Winter Garden, you might make a stop by sights like West Orange Trail and Central Florida Railroad Museum.

Killarney map

Killarney

If you're looking for some top things to see and do in Killarney and surrounding area, you can visit Bella Collina Golf Club and West Orange Trail.

Top Oakland Hotel Reviews

Frequently asked questions

What's it like in Oakland?

Travelers will be sure to enjoy their time in Winter Garden's Oakland neighborhood. Consider a visit to Oakland Nature Preserve as part of your Oakland travel plans.

How many hotels should I expect to find in the Oakland area?

Expedia has 7 Oakland hotels and other accommodations, and one might make a good home base for venturing out into the greater Winter Garden area.

If I need to cancel my hotel reservation in Oakland, will I receive a refund?

Yes, the majority of room reservations are refundable if you cancel before the hotel’s cancellation deadline, which is usually within 24-48 hours of your arrival date. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within 24 hours of booking. Enter dates in and click on "Search", then use the "fully refundable" filter to get the top deals on offer in Oakland.

Where can I learn more about changing or cancelling my trip to Oakland?

For more information about picking new dates or cancelling your trip to Oakland, go to https://www.expedia.com/service/.

What is there to do in this Winter Garden neighborhood?

Oakland Nature Preserve is an attraction you might want to check out while you're in Oakland. While you're out sightseeing in Winter Garden, be sure to visit other sights like Plant Street Market or Resurrection Catholic Church.