Top Winter Garden Hotel Deals

Make the Most of Your Winter Garden Stay

A charming city with a citrus legacy

Winter Garden offers something increasingly rare in Central Florida: an authentic small-town atmosphere just 20 minutes west of Orlando. This former citrus hub has transformed its historic downtown into a sophisticated destination where the 22-mile West Orange Trail runs directly down brick-lined Plant Street, creating a unique corridor of preserved early 20th-century architecture, independent boutiques, and elevated dining. The restored 1935 Garden Theatre anchors the cultural scene, while Plant Street Market's artisan vendors and Crooked Can Brewing Company provide a contemporary gathering space that honors the city's agricultural past.

Culinary experiences and local character

The dining scene punches well above expectations. The Chef's Table at the Edgewater delivers prix fixe fine dining in the historic 1927 hotel, while Matthew's Steakhouse and Market to Table offer refined American cuisine. What sets Winter Garden apart is its walkable downtown where locals navigate by golf cart, creating an unhurried pace that contrasts sharply with Orlando's theme park intensity. The Saturday Farmers Market draws crowds for quality vendors and live entertainment.

Practical considerations

You'll want a rental car from Orlando International Airport (26 miles southeast), as public transit remains limited beyond downtown. The city serves as an excellent base for exploring Mount Dora or Wekiwa Springs, both within 30 minutes.

Frequently Asked Questions about Winter Garden

Can I use my miles on Delta Stays to book hotels in Winter Garden?

Yes, you can book your hotel stay in Winter Garden using your Delta miles, or a combination of miles and cash. When you log in to your Delta SkyMiles® account, you will also discover Member offers at select properties that could enhance your travel experience.

What is the benefit of booking my Winter Garden hotel directly on Delta Stays?

As a SkyMiles Member, you will earn 2 miles per $1 you spend on completed hotel stays and vacation rentals booked through Delta Stays. You will also enjoy access to special Member offers at select properties, and have the flexibility to pay with miles, cash, or a combination of both. To ensure you earn miles when paying fully with cash, simply sign in to your SkyMiles account or enter your SkyMiles number at checkout. Please allow up to 8 weeks after completing a stay for miles to appear in the SkyMiles account provided. Please also note that if you use miles to pay for any portion of your stay, you will not earn miles on that reservation, including any amount paid with cash.

Is it possible to change or cancel my hotel booking made through Delta Stays?

Cancellation policies vary by property. We suggest reviewing the cancellation policies displayed in the detailed information for each hotel before completing your reservation. You will notice that refundable options are available for some rates, while others may be non-refundable. Please note that if you make changes to or cancel your booking, this may affect the number of miles you earn and receive in your account.

Can I use my Delta SkyMiles® American Express® Card to book?

Yes, your Delta SkyMiles® Gold, Platinum, or Reserve American Express® Card gives you access to additional miles and benefits including an annual statement credit of up to $200 to use on prepaid hotels or vacation rentals booked through Delta Cars and Stays. Note that terms apply to these offerings. For an overview of all advantages associated with your card membership, please visit the Delta SkyMiles® American Express Credit Cards page where you can review complete benefit details.

Can I earn MQDs on Delta Stays hotel bookings?

Periodically, Delta Stays offers opportunities for SkyMiles Members to accumulate Medallion® Qualification Dollars through hotel and vacation rental reservations completed using Delta Stays. Be sure to check out the latest MQDs offers and terms at the Delta Stays MQD Offer page.

Do I need to have a Delta SkyMiles account to book hotels on Delta Stays?

Delta Stays provides hotel booking services to all customers. However, registering as a SkyMiles Member enhances your experience by allowing you to earn miles and access Member pricing and promotions. Members can earn 2 miles per $1 spent (excluding taxes and other fees) on Delta Cars and Stays, and it is free to join. Visit the delta.com to join today.

Can I book a vacation rental through Delta Stays?

Yes, Delta Stays extends beyond conventional hotel offerings to include a wide selection of vacation rentals for your travel accommodations. You can explore a variety of homes, condos, and distinctive accommodations powered by Vrbo on the Vacation Rentals page.

What hotels in Winter Garden have high ratings?

You will find 13 hotels in Winter Garden to choose from when you book on Delta Stays. Hilton Vacation Club Aqua Sol Orlando West has a guest rating of 8.8 out of 10, and features 2 outdoor pools and a children's pool. Another top-rated hotel is SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance and guests love its outdoor pool and heated pool and the free buffet breakfast. TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance has a rating of 9 including good ratings for the outdoor pool and heated pool. The hotel has a hot tub and a restaurant.

What's a good time of year to visit Winter Garden?

To experience Winter Garden during great weather, consider a visit in April when the temperature averages 73°F and the skies are mostly sunny with light rainfall. For off-peak prices and more deals on hotels, consider visiting during September when temperatures reach a warm 82°F with sunny skies and lower visitor numbers.

Which hotels in Winter Garden are located near Disney's Palm Golf Course?

Redesigned by Arnold Palmer in 2013, this championship course winds through Florida woodlands with 59 bunkers and a dramatic 18th hole where your approach must clear wrapping water. Disney's Grand Floridian Resort & Spa is a popular hotel, which is just steps away. Another top hotel is Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort and it is within a short drive.

Which hotels in Winter Garden are located near Disney's Magnolia Golf Course?

This championship course winds through 1,500 magnolia trees with 11 water hazards and the famous Mickey Mouse-shaped bunker on hole 6, blending serious golf with Disney® charm. One popular hotel is Disney's Grand Floridian Resort & Spa which is steps away. Four Seasons Resort Orlando at WALT DISNEY WORLD® Resort is another well-reviewed hotel and it is within a short drive.

Which hotels in Winter Garden are near Surfari Water Park?

Ride the dual FlowRider surf simulator or float along the 695-foot lazy river at this tropical water park. Morning visits offer shorter lines for the slides. Disney's Animal Kingdom Lodge is a popular hotel, which is just a short drive away. Hilton Vacation Club Aqua Sol Orlando West is another well-reviewed hotel and it is within a short drive.

*Terms and conditions:

Mileage Offer:

SkyMiles Members will earn two (2) miles per US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Opens in a new window on the base hotel rate for a completed hotel stay. Base hotel rate is the cost of the hotel room, before taxes and fees, charged at the time of booking or upon checkout. Taxes and fees, gratuities, room service other booking charges, or any bookings which are paid or reduced by miles, redemption vouchers or discount codes are excluded from mileage credit. For clarity, if miles are used as a form of payment (whether for all or a portion of the booking), no portion of the booking will be eligible to earn miles under this offer. Except with respect to the Hertz Mileage offer (listed below), SkyMiles Members will earn two (2) miles per eligible US$1 or equivalent foreign currency spent at https://carsandstays.delta.com/Cars on the base car rental rate for a completed car qualifying rental booking (“Qualifying Dollars”). A qualifying rental booking includes rentals at a participating location for one or more days at rates other than travel industry rates or discounts, wholesale of tour package rates or discounts, wholesale tour package rates, insurance/dealer replacement rates, corporate and government rates, group travel discounts, or rentals in conjunction with a frequent flyer car award, or other corporate agreements applicable to the respective car company. Calculation of the applicable standard mileage offer is listed below by car rental company. Qualifying Dollars include the base car rental rate, which is the cost of the car rental before taxes and fees, charged at the time of booking. Taxes, fees, other incidental charges, or other booking charges or any bookings which are paid or reduced by redemption vouchers or discount codes are excluded from mileage credit and are not included in the Qualifying Dollars.

This mileage offer does not apply to stays or car rentals booked through Delta Vacations or any cruises booked through Delta Cruises.

Standard mileage offer for car rentals booked at https://www.delta.com/Opens in a new window or https://carsandstays.delta.com/Opens in a new window:

Hertz Reservations:

• General SkyMiles Members earn 4 miles per Qualifying Dollar

• Silver Medallions earn 5 miles per Qualifying Dollar

• Gold Medallions earn 6 miles per Qualifying Dollar

• Platinum Medallions earn 7 miles per Qualifying Dollar

• Diamond Medallions earn 8 miles per Qualifying Dollar

Dollar and Thrifty Reservations:

• All SkyMiles Members earn 4 miles per Qualifying Dollar

Alamo, Enterprise, National, Avis, Budget, Payless and SIXT Reservations:

• All SkyMiles Members earn 2 miles per Qualifying Dollar