A brick building with a clock tower and a sign that reads "Winter Garden."

2 Star Hotels in Winter Garden

City, hotel name, or address

Dates

Travelers

I'm traveling for business

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight

Tomorrow

Next weekend

In two weeks

2 Star Hotels in Winter Garden

A laundry area with a washing machine, dryer, and a wall-mounted decorative piece.

A modern kitchen with stainless steel appliances, white cabinetry, and a view to a balcony with outdoor furniture.

A rectangular swimming pool with a brick deck, surrounded by tall trees and lounge chairs.

A hotel room with a bed, two bedside tables, a nightstand, a balcony with a view, and two wall-mounted mirrors.

1. Upstay Large Family Condo w Pool Sauna

Winter Garden

$86

$273 total

includes taxes & fees

Oct 14 - Oct 15

A modern living room with a sofa, green chairs, a coffee table, and a kitchen in the background.

An aerial view of a resort with a large central pool, multiple lounge areas, and surrounding greenery.

2. Upstay - Condo w Hot Tub and Pool - Near Disney

Winter Garden

$93

$250 total

includes taxes & fees

Oct 11 - Oct 12

An aerial view of a resort with a large, irregularly shaped pool surrounded by lounge chairs and umbrellas, set against a backdrop of palm trees and a multi-story building.

A gym with exercise equipment, large windows, and a view of greenery.

A balcony with a view of a forest, a table with chairs, and a ceiling fan.

3. Modern 3BR Condo Near Disney- Pool and Hot Tub

Winter Garden

$85

$242 total

includes taxes & fees

Nov 2 - Nov 3

A modern living room with a TV, seating area, kitchen, and a ceiling fan.

A balcony with a view of a green landscape, a table with chairs, and a railing.

4. Upstay - Condo Near Disney w Pool Hot tub Sauna

Winter Garden

$88

$245 total

includes taxes & fees

Oct 11 - Oct 12

A covered balcony with wicker chairs, a ceiling fan, and a view of trees.

A spacious lobby with leather sofas, a central coffee table, and large windows offering a view of greenery outside.

5. Upstay Tropical Style Family Condo w Pool

Winter Garden

$74

$259 total

includes taxes & fees

Oct 12 - Oct 13

6. Upstay Stylish 3BR Condo w Patio Near Disney

Winter Garden

$84

$271 total

includes taxes & fees

Oct 14 - Oct 15

A dining area with a round table set for four, surrounded by wicker chairs.

A spacious lobby with a high ceiling, large windows, and a mix of seating areas including sofas and tables.

A spacious living room with a grey sofa, a coffee table, and a large plant. There is a balcony with outdoor furniture and a TV mounted on the wall.

7. Upstay - Modern Family Apartment w Pool Hot Tub

Winter Garden

$106

$263 total

includes taxes & fees

Nov 3 - Nov 4

A modern living room with a sofa, coffee table, and a ceiling fan.

8. Upstay 3BR Condo w Pool Patio Near Disney

Winter Garden

$80

$266 total

includes taxes & fees

Nov 2 - Nov 3

A spacious lobby with a large seating area, a flat-screen TV mounted on the wall, and large windows offering a view of the outdoors.

An aerial view of a resort with a large swimming pool, sun loungers, and palm trees.

A spacious lobby with a large sofa, a coffee table, and a TV mounted on the wall.

A hotel with a rooftop pool, surrounded by lush greenery and a view of the landscape.

9. Upstay Modern 2BR Condo Near Disney

Winter Garden

$107

$273 total

includes taxes & fees

Oct 12 - Oct 13

A modern kitchen with a dishwasher, a dining area with a table and chairs, and a view of the outside.

A spacious living area with a sofa, coffee table, and a view of the kitchen.

10. Upstay - Condo Near Disney w Pool-spa-sauna-games

Winter Garden

$78

$240 total

includes taxes & fees

Nov 2 - Nov 3

A breakfast area with a counter, coffee machines, and a chalkboard menu.

A snack and beverage kiosk with a variety of snacks and drinks, including a 'Fuel Up' and 'Snacks to Go' section, and a 'Chill Out' cooler.

A Hampton Inn hotel with a modern design, featuring a prominent entrance with a blue canopy and a large sign.

A reception desk with a "Welcome to the Sun Shine State" sign, a "Hilton" sign, and a "Fats" sign.

11. Hampton Inn By Hilton Ocoee Orlando

Ocoee

$114

$128 total

includes taxes & fees

Oct 25 - Oct 26

A spacious indoor area with multiple tables and chairs, a sofa, and a door marked "EXIT".

A hotel room with two beds, a blue sofa, a TV mounted on the wall, and a desk with a chair.

A hotel lobby with a reception desk, a computer station, and seating area with chairs and a sofa.

A reception area with a check-in counter, a reception desk, and a wall with a geometric design.

12. Holiday Inn Express Hotel & Suites Ocoee East by IHG

Orlando

$109

$123 total

includes taxes & fees

Oct 11 - Oct 12

A hotel room with a bed, a desk, a TV, and a sofa.

A hotel room with a living area, kitchenette, and a large window with curtains.

A hotel room with a desk, chair, TV, and a cabinet with a mirror.

A large building with a prominent tower, surrounded by parking lots and a highway.

13. Hampton Inn & Suites Clermont

Clermont

$114

$127 total

includes taxes & fees

Oct 25 - Oct 26

A Hampton Inn hotel with a modern design, featuring a clear entrance, a flag, and a well-lit exterior.

A hotel reception desk with a 'Welcome to the Sun Shine State' sign, a reception area, and a bookshelf with various items.

A hotel room with a large bed, a desk, a chair, a window with blinds, a wall-mounted TV, and a painting.

A modern hotel lobby with a long communal table, blue and red seating, and a patterned carpet.

14. Hampton Inn Kissimmee North

Kissimmee

$110

$124 total

includes taxes & fees

Nov 1 - Nov 2

A spacious dining area with a long table and multiple seating options, including booths and chairs.

A hotel entrance with a covered patio, columns, and a glass door leading inside.

A hotel room with two beds, a nightstand with a lamp, and a painting on the wall.

A modern kitchen with a sink, dishwasher, microwave, and a round mirror above the counter. There is a dining table with chairs and a coffee machine on the counter.

15. Quality Inn & Suites By the Parks

Kissimmee

$75

$85 total

includes taxes & fees

Oct 26 - Oct 27

A hotel with a pool, outdoor seating, and a sign for 'Galleria'.

An aerial view of a swimming pool with lounge chairs and a small waterfall feature.

A hotel room with a bed, desk, chair, and a TV on the wall.

A hotel lobby with a reception desk, two armchairs, a potted plant, a telephone, and a carpeted floor. There are two doors in the background, one with a sign indicating room numbers.

16. Galleria Palms Hotel

Kissimmee

$67

$98 total

includes taxes & fees

Oct 13 - Oct 14

A hotel with a swimming pool, outdoor seating, and a covered area.

A hotel with a prominent sign, a central tower, and a covered entrance area.

A hotel room with two beds, a desk with a chair, a television, and a door.

A playground with a castle-like play structure, a slide, and a climbing wall.

17. JC Inn

Clermont

$72

$81 total

includes taxes & fees

Oct 11 - Oct 12

A modern lobby with a reception desk, seating area, and a large screen.

A hotel room with two beds, a TV mounted on the wall, and a large window with curtains.

A modern hotel lobby with a reception desk, seating area, and a children's play area.

A modern kitchen with a built-in oven, a coffee maker, and a sink. There is a desk with a chair and a flat-screen TV mounted on the wall.

18. Springhill Suites By Marriott Orlando Altamonte Springs

Altamonte Springs

$101

$115 total

includes taxes & fees

Oct 19 - Oct 20

A hotel room with a bed, a desk, a coffee maker, and a microwave.

A compact kitchen with a microwave, coffee maker, sink, and dishwasher.

A modern kitchen with a black refrigerator, a microwave, and a coffee maker. There is a dining table with chairs and a bulletin board on the wall.

A hotel room with a brown sofa, two patterned pillows, a side table with a lamp, and a large window offering a view of a park and buildings.

19. Candlewood Suites Orlando - Lake Buena Vista by IHG

Orlando

$58

$65 total

includes taxes & fees

Oct 13 - Oct 14

A modern hotel lobby with a reception desk, a self-service kiosk, and a seating area.

A modern kitchen with dark cabinetry, a granite countertop, and a backsplash with a floral pattern.

A hotel with a modern design, featuring a prominent 'Suburban Studios' sign, a covered entrance, and a parking lot with handicapped accessibility.

A hotel room with a bed, a desk, a chair, a lamp, and a window with curtains.

20. Suburban Studios Orlando - Ocoee/Winter Garden

Ocoee

$85

$95 total

includes taxes & fees

Nov 1 - Nov 2

See more properties

Top neighborhoods in Winter Garden

A tree-lined sidewalk with parked cars and a clear sky.

A street lined with large trees and historic brick buildings, including a 'Local' sign.

A bakery interior with a display case, shelves with jars, and a counter with a menu board.

A café with a variety of food items and beverages on display, including boxes of snacks and bottles of wine.

A bar with a polished floor, metal chairs, and a brick wall with a TV.

Downtown Winter Garden

Plant Street bursts with small-town charm in Downtown Winter Garden. The restored 1935 Garden Theatre anchors the brick-lined pedestrian zone where locals and visitors stroll past historic storefronts. Hop on the West Orange Trail for a scenic bike ride or browse the weekly farmers market for fresh Florida citrus and artisanal goods. Farm-to-table restaurants with outdoor seating line the main drag, while boutique bed & breakfasts offer cozy accommodations in restored buildings. The pedestrian-friendly layout means you can park once and explore everything on foot, from antique shops to the Central Florida Railroad Museum.

See properties

A city skyline at dusk with illuminated buildings reflecting on a calm body of water.

Horizon West

Winter Garden's Horizon West neighborhood has a host of places to visit such as Walt Disney World® Resort and Orange County National Golf Club.

See properties

A sunset over a body of water with silhouetted land in the distance and tall grasses in the foreground.

Vista del Lago

Vista del Lago is a peaceful retreat just minutes from Orlando's major attractions. Vacation homes with private pools and resort amenities offer the perfect landing spot after action-packed theme park days. Disney's Animal Kingdom and Magic Kingdom are just a short drive away, while community pools provide refreshing breaks between adventures. Dining options require a quick drive to nearby Championsgate or Disney Springs, where choices range from casual to upscale. Most travelers appreciate having rental cars to navigate between the quiet neighborhood and Orlando's entertainment districts. Many vacation rentals feature full kitchens and game rooms, creating the ideal home base for family theme park trips.

See properties

A wooden pier extending into a calm body of water, surrounded by lush greenery and a distant forest.

A calm lake with lily pads and reeds in the foreground, surrounded by trees and a cloudy sky.

Oakland

Oakland's historic charm lives on through preserved Victorian homes and oak-canopied streets. Wander downtown to discover the 1889 Healthy House Museum and local artisan shops. The 128-acre Oakland Nature Preserve invites you to explore cypress wetlands and spot some of the 200+ bird species that call Lake Apopka home. Southern comfort food dominates the dining scene with most spots closing early. The area is best explored by car, though downtown remains pleasantly walkable. Cozy bed and breakfasts in historic homes offer an intimate alternative to Orlando's bustling tourist accommodations just 15 minutes away.

See properties

Killarney

Killarney offers a peaceful retreat from Orlando's tourist bustle while keeping adventure within reach. The Oakland Nature Preserve invites you to explore scenic trails while the nearby West Orange Trail is perfect for morning bike rides. Lake Apopka provides a serene backdrop for fishing or simply watching the sunset paint the Florida sky. When you're ready for more action, Winter Garden's charming downtown is just minutes away. Accommodation options include budget-friendly extended-stay hotels and vacation homes with pools and kitchenettes. A car is essential for getting around, though rideshare services are readily available. The quiet suburban streets make evening strolls pleasant after busy days exploring nearby attractions.

See properties

Top landmarks in Winter Garden

Flamingo Crossings Town Center

8.6/10 (131 reviews)

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

See properties

Disney's Palm Golf Course

8.4/10 (457 reviews)

You might want to practice your swing at Disney's Palm Golf Course, a golf course located 11.2 mi (18.1 km) from central Winter Garden. If Disney's Palm Golf Course doesn't quite scratch your golfing itch, Grand Cypress Golf Club, and Orange Lake Golf are also nearby.

See properties

Orange County National Golf Club

8.4/10 (647 reviews)

You might want to play some rounds at Orange County National Golf Club, located 8.9 mi (14.4 km) from central Winter Garden. If Orange County National Golf Club doesn't quite scratch your golfing itch, Disney's Palm Golf Course, and Disney's Magnolia Golf Course are also nearby.

See properties

Disney's Magnolia Golf Course

8.4/10 (552 reviews)

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, Disney's Palm Golf Course, and Orange Lake Golf are also nearby.

See properties

Surfari Water Park

9.0/10 (2,086 reviews)

If thrills are what you're after, head to Surfari Water Park, located 2.3 mi (3.8 km) from central Four Corners. If you have fun at Surfari Water Park, you'll love Disney's Animal Kingdom® Theme Park and Island H2O Live!, both located nearby.

See properties

West Orange Trail

8.4/10 (337 reviews)

Downtown Winter Garden is home to West Orange Trail, so why not stop by during your stay in Winter Garden. Winter Garden has lots of other activities such as Camping World Stadium and Kia Center.

See properties

Garden Theatre

8.4/10 (219 reviews)

If you want to see a show while you're in town, try and grab some tickets at Garden Theatre in Downtown Winter Garden. If you want to experience more of the culture Winter Garden has to offer, head to Winter Garden Heritage Museum, West Orange Trail, and AdventHealth Winter Garden.

See properties

Disney's Oak Trail Golf Course

8.4/10 (377 reviews)

You might want to play some rounds at Disney's Oak Trail Golf Course, located 11.2 mi (18 km) from central Winter Garden. If Disney's Oak Trail Golf Course doesn't quite scratch your golfing itch, Disney's Palm Golf Course, and Orange Lake Golf are also nearby.

See properties