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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
In one month
22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

Featured Cottages in Winter Garden

Orlando Lakefront Tiny House Community
Relax in a serene outdoor space with a deck overlooking a tranquil body of water, surrounded by lush greenery.

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (324)
"We enjoyed our stay, I loved the the view of the lake from the main bedroom ,it’s a beautiful and relaxing place."
The price is NZ$266
includes taxes & fees
27 July - 28 July
Orlando Lakefront Tiny House Community
Lafitte's Landing Lakeview Cottage - Lakefront!
House, Multiple Beds, Patio, Garden View (Lafitte's Landing Lakeview Cottage) | Outdoor dining

Lafitte's Landing Lakeview Cottage - Lakefront!

3.0 star property
10.0 out of 10, Exceptional, (7)
"Beautiful Cottage and enjoyed the back deck overlooking the lake. Great family vacation spot."
Lafitte's Landing Lakeview Cottage - Lakefront!
Tiny Hidden Cottage
Enjoy a meal with a view from this kitchen, featuring a large window and a potted plant.

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (48)
"Host provided eggs from chickens that roost on the property - nice extra!"
The price is NZ$253
includes taxes & fees
25 July - 26 July
Tiny Hidden Cottage
8000 Lost Shaker Lane
Welcome to Margaritaville, a charming two-story residence with a front porch and lush garden.

8000 Lost Shaker Lane

3.0 star property
9.6 out of 10, Exceptional, (7)
"The house is absolutely beautiful. Very clean and has everything you need. Unfortunately you can’t use the pool which I didn’t understand so that was the only downside. The property is gorgeous. "
8000 Lost Shaker Lane
Family 4BR Home w/ Resort Pool Near Disney
House (4 Bedrooms) | Floor plan

Family 4BR Home w/ Resort Pool Near Disney

3.0 star property
Family 4BR Home w/ Resort Pool Near Disney
Cozy Cottage 3 blocks from town
Stroll through the charming streets of this vibrant commercial area, lined with traditional storefronts and palm trees.

Cozy Cottage 3 blocks from town

10.0 out of 10, Exceptional, (33)
"Cute and more than sufficient for a few day stay in beautiful Mount Dora-Loved the quaint town and Debbie was a great host"
Cozy Cottage 3 blocks from town
Easy walk 5 blocks to downtown dining & shopping. 2 BR, 2 Bath, POOL
Relax in this inviting outdoor space with a sofa, chairs, and glass-top table.

Easy walk 5 blocks to downtown dining & shopping. 2 BR, 2 Bath, POOL

9.6 out of 10, Exceptional, (23)
"The convenient location, clean property and fair cost made our stay! "
Easy walk 5 blocks to downtown dining & shopping. 2 BR, 2 Bath, POOL
Historic Tremain Cottages
Stroll through the charming front yard, surrounded by lush greenery and a white picket fence, to the inviting porch area.

Historic Tremain Cottages

3.0 star property
8.4 out of 10, Very good, (31)
"Great location!"
Historic Tremain Cottages
Mount Dora Cottages
Charming single-story home with a gabled roof and inviting front porch.

Mount Dora Cottages

3.0 star property
9.4 out of 10, Exceptional, (208)
"Our family loved this place and the neighborhood is perfect for a quiet afternoon. "
The price is NZ$342
includes taxes & fees
31 July - 1 Aug
Mount Dora Cottages
Oaktree Cottage in Mount Dora Historic District
Stunning single-story building with a front door, glass panel, and small porch area.

Oaktree Cottage in Mount Dora Historic District

9.8 out of 10, Exceptional, (7)
"Tastefully decorated and well equipped rental. Convenient walk to downtown "
Oaktree Cottage in Mount Dora Historic District
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Exterior

Charming 2-bedroom Country Cottage in Kissimmee with private parking

10.0 out of 10, Exceptional, (2)
"The house was exactly as shown. It was very clean and really nice. Great space for parking my large trailer. The neighborhood was nice and very quiet. We would definitely stay again."
The price is NZ$251
includes taxes & fees
4 Aug - 5 Aug
Charming 2-bedroom Country Cottage in Kissimmee with private parking
The Ingram * 3 min walk to Downtown Mt. Dora!!
Situated on a well-maintained lawn, this charming house features a front porch with two chairs and a small table.

The Ingram * 3 min walk to Downtown Mt. Dora!!

9.8 out of 10, Exceptional, (43)
"Excellent, had a great time. Had everything u could need. "
The Ingram * 3 min walk to Downtown Mt. Dora!!
Florida Guest House with Private pool & WiFi
Welcome to a charming single-story home with a red door, surrounded by lush greenery and a wooden fence.

Florida Guest House with Private pool & WiFi

9.8 out of 10, Exceptional, (38)
"Wonderful stay. This is my second time here and love the accommodations and location. Very quiet. "
The price is NZ$444
includes taxes & fees
10 Aug - 11 Aug
Florida Guest House with Private pool & WiFi
5003 Windermere Avenue
Relax by the pool with a meal at this outdoor dining area, featuring a table and chairs under a pendant light.

5003 Windermere Avenue

3.0 star property
10.0 out of 10, Exceptional, (2)
"Great location, convenient to all shopping needs. Close to Disney World. Good amenities. Great for families traveling together."
5003 Windermere Avenue
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
Enjoy dining al fresco with a view of the surrounding buildings from this outdoor patio, featuring a table, chairs, and a sofa.

Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621

3.0 star property
Amazing Game Room, Harry Potter, Mickey & Princess Room. All new Decor! #7sl1621
Gorgeous Cottage w/Private Pool + Balcony, Near Disney!
Overlooking a charming street lined with pastel-hued houses, this residence features a balcony with a white railing.

Gorgeous Cottage w/Private Pool + Balcony, Near Disney!

9.8 out of 10, Exceptional, (48)
"We had a great stay! Very clean, spacious for a family of 4, easy access to Disney parks, food/shopping. Will definitely stay again! "
Gorgeous Cottage w/Private Pool + Balcony, Near Disney!
The Beauclair * 3 min walk to Downtown Mt. Dora!!
Stunning two-story home with a covered entryway and balcony, surrounded by a beautifully manicured lawn.

The Beauclair * 3 min walk to Downtown Mt. Dora!!

10.0 out of 10, Exceptional, (50)
"Nice place, near downtown, walkable, away from noise roads. Easy parking. I recommend "
The Beauclair * 3 min walk to Downtown Mt. Dora!!
Private Patio: College Park Cottage in Orlando!
Welcome to a serene single-story home surrounded by a lush lawn and a majestic tree.

Private Patio: College Park Cottage in Orlando!

10.0 out of 10, Exceptional, (8)
"I stayed here for a month with my dog. It was exactly what I needed! The hosts thought of everything that you could possibly need. There is a ton of space and everything is organized and clean. Location is great being close to local shops, necessities, and major roads."
Private Patio: College Park Cottage in Orlando!
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
Fitness center entrance with a welcoming walkway and lush surroundings.

Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003

3.0 star property
Stunning Villa With Themed Room's and Game Room, Right Across From the Club House #7sl9003
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Traditional home with a gabled roof and front porch, surrounded by lush gardens.

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

10.0 out of 10, Exceptional, (25)
"Easy and convenient in a nice place "
The price is NZ$579
includes taxes & fees
5 Aug - 6 Aug
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
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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Top Winter Garden Hotel Reviews

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings

10/10 Excellent
"Very nice rooms, breakfasts vary frequently, area for my pets, everything very clean and a very pleasant aroma. I would definitely stay there again."
Rocio G 5-night trip
Posted 14 hours ago
Home2 Suites by Hilton Orlando at Flamingo Crossings

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between NZ$251 and NZ$579 per night. These stays offer a chance to get reacquainted with nature — at a price you can afford. 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 is there to do in Winter Garden near my cottage?
Whatever you're into, Winter Garden has plenty of things to keep you on the go. Orange County National Golf Club, Resurrection Catholic Church and West Orange Trail are on many travellers' agendas. Don't forget to explore Winter Garden Art Association, Winter Garden Heritage Museum and Oakland Nature Preserve either. With Expedia's Winter Garden hotel deals, you'll be able to see more renowned attractions like these with the cash you save.