Find Hotels with Connecting Rooms in Winter Garden, FL

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Our top choices for Winter Garden hotels with connecting rooms

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

2.5 star property
Bay Lake
9.4 out of 10, Exceptional, (4315)
"Really good place to stay "
United States
Lians
$116 nightly
The price is $130
Jan 4 - Jan 5, 2026
Total with taxes and fees
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Home2 Suites by Hilton Orlando at Flamingo Crossings

3.0 star property
Bay Lake
9.2 out of 10, Wonderful, (5059)
"Great location nice breakfast and front desk people is amazing "
United States
Orlando
$103 nightly
The price is $116
Dec 16 - Dec 17
Total with taxes and fees
Home2 Suites by Hilton Orlando at Flamingo Crossings

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

3.5 star property
Bay Lake
9.0 out of 10, Wonderful, (2250)
"Great stay"
United States
Christopher
$114 nightly
The price is $128
Dec 21 - Dec 22
Total with taxes and fees
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

3.0 star property
Bay Lake
9.6 out of 10, Exceptional, (1969)
"Great stay"
United States
Windy Laine
$143 nightly
The price is $161
Jan 5 - Jan 6, 2026
Total with taxes and fees
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Holiday Inn Express & Suites Clermont Se West Orlando by IHG

2.5 star property
Clermont
8.4 out of 10, Very Good, (1057)
"Great room great breakfast"
United States
Kelly
$110 nightly
The price is $122
Jan 7 - Jan 8, 2026
Total with taxes and fees
Holiday Inn Express & Suites Clermont Se West Orlando by IHG

Rosen Shingle Creek

4.5 star property
Orlando
9.4 out of 10, Exceptional, (4338)
"Great resort "
United States
Camille
$102 nightly
The price is $115
Dec 14 - Dec 15
Total with taxes and fees
Rosen Shingle Creek

Hyatt Regency Orlando International Airport

4.0 star property
Orlando
9.4 out of 10, Exceptional, (3824)
"Loved our stay there! Was perfect for traveling early in the morning. "
United States
Andrea
$166 nightly
The price is $186
Dec 24 - Dec 25
Total with taxes and fees
Hyatt Regency Orlando International Airport

Red Lion Hotel Orlando Lake Buena Vista South

3.5 star property
Kissimmee
8.8 out of 10, Excellent, (4250)
"Beautiful place to stay, reliable price, the location was perfect, super clean, definitely I will return back in a future to this hotel."
United States
Aurelis
$88 nightly
The price is $100
Dec 14 - Dec 15
Total with taxes and fees
Red Lion Hotel Orlando Lake Buena Vista South

Hilton Vacation Club Mystic Dunes Orlando

4.0 star property
Kissimmee
9.0 out of 10, Wonderful, (4471)
"It was a great stay"
United States
Glynnis
$128 nightly
The price is $145
Dec 16 - Dec 17
Total with taxes and fees
Hilton Vacation Club Mystic Dunes Orlando

Ramada by Wyndham Suites Orlando Airport

3.0 star property
Airport North
8.2 out of 10, Very Good, (5171)
"Great place to stay close to airport "
United States
Rebekah
$89 nightly
The price is $100
Dec 10 - Dec 11
Total with taxes and fees
Ramada by Wyndham Suites Orlando Airport
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.

Find out more about Winter Garden

Discover top Winter Garden attractions

Winter Garden, Florida, offers a delightful blend of outdoor adventure and charming community vibes, perfect for quality-seeking travelers. Start your exploration at the beautiful **Winter Garden Village**, where upscale shopping meets delightful dining options, making it a family-friendly hub. Don’t miss **Lake Apopka**, where you can enjoy scenic trails perfect for hiking or biking, offering stunning views of wildlife and nature. For a taste of local culture, the **Winter Garden Historic District** is a must-visit, featuring quaint shops and the popular **Garden Theatre**, which showcases a variety of performances throughout the year. For those looking for a unique experience, the **West Orange Trail** is ideal for cycling or leisurely walks, taking you through picturesque landscapes. After a day of exploration, consider staying at a hotel in the downtown area, where you can enjoy easy access to these attractions, as well as cozy accommodations that prioritize guest comfort and satisfaction, ensuring you and your family feel pampered and well-taken care of during your stay.

Find the best hotels with connecting rooms in Winter Garden

For families or groups traveling together to Winter Garden, Florida, these top hotels offer convenient connecting rooms to enhance your stay. Each hotel ensures comfort and accessibility for everyone in your party.

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

  • Why it's great for extra space: Travelers seeking connecting rooms will find the Residence Inn by Marriott Orlando a perfect fit, with an impressive review rating of 9.6. This hotel not only offers spacious connecting accommodations but also features kitchenettes with dishwashers and dining tables, making it ideal for longer stays or families. Guests can start their day with a free breakfast and enjoy leisure time at the outdoor pool.
  • Other amenities: The hotel further enhances comfort with a rooftop garden, a fitness center that is accessible 24 hours, and a cozy poolside bar. Guests can rely on daily housekeeping services, and amenities such as a toaster, stovetop, and cookware make meal preparation easy. The hotel also includes convenient self-parking and an on-site grocery store, ensuring a straightforward experience for all.
  • Neighborhood: Bay Lake
  • Nearby attractions: Orange Lake Golf - 3.65 miles, Island H2O Live! - 3.76 miles, Flamingo Crossings Town Center - 0.19 miles

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

  • Why it's great for extra space: The Fairfield by Marriott Inn & Suites Orlando is an excellent choice for travelers looking for connecting rooms, a remarkable guest review rating of 9.4. With its connecting room options, families can enjoy the comfort of spacious rooms while maintaining privacy. Guests will appreciate the complimentary buffet breakfast that caters to all tastes, along with a refreshing outdoor pool that invites relaxation after a day of exploring.
  • Other amenities: Additionally, this hotel offers a fitness center available 24 hours, rooftop garden for unwinding, and convenient self-parking options. The hotel features family-friendly amenities such as a poolside bar and children’s meals at the restaurant. Guests can also take advantage of the complimentary toiletries, microwave in rooms, and a grocery store on-site for added convenience.
  • Neighborhood: Bay Lake
  • Nearby attractions: Orange Lake Golf - 3.81 miles, Island H2O Live! - 3.92 miles, Flamingo Crossings Town Center - 0.17 miles

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

  • Why it's great for extra space: SpringHill Suites Orlando offers a welcoming place for guests needing connecting rooms, with a solid review rating of 9.0. Families will appreciate the spacious suites that feature separate living areas and sofa beds, allowing for comfortable gatherings. The hotel also serves a free breakfast daily, ensuring everyone starts their day right, and guests can unwind in the outdoor heated pool or hot tub.
  • Other amenities: Additional amenities include a rooftop garden, 24-hour fitness facilities, and a snack bar for easy refreshments. This hotel also offers flexible check-in and check-out options, and contactless service for added convenience. Guests can enjoy a game room and child-friendly window designs, making it a delightful choice for families.
  • Neighborhood: Bay Lake
  • Nearby attractions: Orange Lake Golf - 3.47 miles, Island H2O Live! - 3.58 miles, Flamingo Crossings Town Center - 0.22 miles

Top Winter Garden Hotel Reviews

Frequently asked questions

How much do hotels with connecting rooms in Winter Garden cost?
Hotels with connecting rooms in Winter Garden range from $100 to $186 per night. These stays offer lots of room for the whole family at a price that won't stretch the budget. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best hotels with connecting rooms in Winter Garden?
Winter Garden offers multiple hotels with connecting rooms with a total average guest review rating of 9.0. Arnold Palmer's Bay Hill Club & Lodge comes highly rated if you're traveling with the family or some friends. Guests staying at this 4-star hotel can access a deep soaking bathtub and pillow top mattresses. Fairfield Inn & Suites Orlando Ocoee is also very popular with travelers. This 2.5-star hotel offers connecting rooms as well as a terrace and designer toiletries.
How many hotels with adjoining rooms are there in Winter Garden?
Take your pick of 2 hotels with adjoining rooms in Winter Garden. No matter if you're vacationing with the kids or planning a getaway with friends, Expedia can help you find the best space for your crew.
What are the best cheap hotels with connecting rooms in Winter Garden?
With hotels with connecting rooms starting from just $100 per night, you may be tempted to stay a little longer in Winter Garden! One property that's easy on the hip pocket is Fairfield Inn & Suites Orlando Ocoee. It comes with the layout you want as well as a swimming pool and premium bedding. Another cost-effective choice is Days Inn by Wyndham Apopka/Orlando. Besides connecting rooms, it offers a swimming pool and individually decorated rooms. If you're exploring Winter Garden and want to save money, there are loads of terrific free attractions to add to your itinerary. Resurrection Catholic Church and West Orange Trail are always favorites. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly hotels with connecting rooms in Winter Garden?
If you're planning an escape in Winter Garden and after a family-friendly hotel with connecting rooms, check out Fairfield Inn & Suites Orlando Ocoee. This 2.5-star property also includes complimentary breakfast and a nearby theme park. Winter Garden has no shortage of family-friendly attractions to explore that'll entertain the kids. Universal Studios Florida and The Wizarding World of Harry Potter™ offer fun for travelers both young and old.
Why book your hotel with connecting rooms in Winter Garden with Expedia?
Booking a hotel with connecting rooms in Winter Garden is as easy as entering your travel dates and picking a place that suits your style. Chasing something luxurious or low cost, or a stay that also comes with a pool and a hot tub? Use Expedia's search filters to further narrow your search results and find your dream fit.
How can I find cheap hotels with connecting rooms in Winter Garden?
With Expedia's filter tool, scoring cheap hotels with connecting rooms in Winter Garden is a cinch. To discover properties that are easy on the wallet, narrow down your search by star rating, amenities and budget.
What is there to do in Winter Garden near my hotel with connecting rooms?
Winter Garden has enough experiences and sights to keep you amused for weeks (or months!), beginning with Winter Garden Heritage Museum. Garden Theatre, Carter Family Bowl and Orange County National Golf Club are other renowned attractions. If you're in town for longer, Resurrection Catholic Church and West Orange Trail are nice final touches to your itinerary.

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