A child riding a bicycle on a wooden boardwalk with a body of water and trees in the background.

Book a Winter Garden Cottage

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Winter Garden cottages

House (2 Bedrooms) | Interior

Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is NZ$965
includes taxes & fees
7 July - 8 July
Fire Pit & Yard: Updated Winter Garden Home!
Front of property

Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (37 reviews)
"Very clean room, quaint, close to the downtown area. "
United States
Raymond
The price is NZ$277
includes taxes & fees
2 July - 3 July
Historic Tremain Cottages
Exterior

Pool Days & Hammock Naps Book Your Escape Before It’s Gone

Pool Days & Hammock Naps Book Your Escape Before It’s Gone
Lake Mary
9.8 out of 10, Exceptional, (59 reviews)
"Absolutely perfect location! It was truly one of the best places we have stayed at!"
United States
Jaelyn M.
The price is NZ$462
includes taxes & fees
6 July - 7 July
Pool Days & Hammock Naps Book Your Escape Before It’s Gone
Interior

Downtown Cottage

Downtown Cottage
Colonialtown North
8.2 out of 10, Very good, (11 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is NZ$318
includes taxes & fees
15 July - 16 July
Downtown Cottage
House (2 Bedrooms) | Interior

Chic Orlando Family Getaway w/ Fenced Yard!

Chic Orlando Family Getaway w/ Fenced Yard!
3.0 star property
Rosemont
10.0 out of 10, Exceptional, (2 reviews)
"The house was well supplied with amenities, family friendly and it was very fun to use the pool and games. There’s a super Walmart and other shops close by."
United States
Jennifer
Chic Orlando Family Getaway w/ Fenced Yard!
Terrace/patio

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (37 reviews)
"Beautiful property in a fantastic location! We've booking this stay twice and will be back again."
United States
Lisa
The price is NZ$595
includes taxes & fees
5 July - 6 July
Incredible Private Lakefront Cottage Retreat
Terrace/patio

Last-Minute July 4th Getaway! Charming Cottage • Early Check-In

Last-Minute July 4th Getaway! Charming Cottage • Early Check-In
Lake Mary
10.0 out of 10, Exceptional, (19 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is NZ$421
includes taxes & fees
6 July - 7 July
Last-Minute July 4th Getaway! Charming Cottage • Early Check-In
Exterior

Charming Historic Cottage with Cozy Porch and Garden Retreat

Charming Historic Cottage with Cozy Porch and Garden Retreat
Polk City
10.0 out of 10, Exceptional, (3 reviews)
"Clean comfort all ok"
United States
Donald P.
The price is NZ$390
includes taxes & fees
21 July - 22 July
Charming Historic Cottage with Cozy Porch and Garden Retreat
Property grounds

Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (23 reviews)
"The setting was very nice and in a quiet area, but conveniently located to travel around Florida. Cottage was clean and very comfortable. Would definitely stay again."
United States
Brenda P.
The price is NZ$549
includes taxes & fees
7 July - 8 July
Cozy Lake Front Cottage
Exterior

Fenced in Backyard! Close to DT Mount Dora! King Bed + Golf Cart Rental!

Fenced in Backyard! Close to DT Mount Dora! King Bed + Golf Cart Rental!
Mount Dora
9.6 out of 10, Exceptional, (4 reviews)
"Perfect location for walking anywhere around downtown. The furnishings, the amenities and the backyard were all that we could have asked for. Would definitely return."
United States
Louis M.
The price is NZ$580
includes taxes & fees
2 July - 3 July
Fenced in Backyard! Close to DT Mount Dora! King Bed + Golf Cart Rental!
Exterior

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

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
College Park
10.0 out of 10, Exceptional, (41 reviews)
"Our hosts were incredibly accommodating and welcoming. This was the perfect place for us to stay while in town for a wedding in Winter Park. Thank you! "
United States
Danielle S.
The price is NZ$609
includes taxes & fees
13 July - 14 July
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Property grounds

Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"

Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Mount Dora
10.0 out of 10, Exceptional, (20 reviews)
"This was a nice charming home my weekend visit to Mount Dora - home was clean, close to downtown and host was a great communicator. "
United States
Rena C.
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
Exterior

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney

Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
Davenport
5.0 out of 10, (2 reviews)
"Needs some upgrades. The bed was a full size, very small for a couple, should really think of upgrading to a king. Pans were old and could use replacing. Bugs and ants constant. Shower was small. Very small tv. Stovetop had missing nob and was difficult to operate. Definitely needs upgrading, left a day early, didn’t feel comfortable there. "
United States
Rebecca F.
The price is NZ$293
includes taxes & fees
2 July - 3 July
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
House (4 Bedrooms) | Interior

Family Resort Home w Pool, BBQ & Game Room

Family Resort Home w Pool, BBQ & Game Room
3.0 star property
Solana
The price is NZ$639
includes taxes & fees
13 July - 14 July
Family Resort Home w Pool, BBQ & Game Room
House (3 Bedrooms) | Interior

Golf, Dine & Unwind Poolside! Haines City Getaway

Golf, Dine & Unwind Poolside! Haines City Getaway
3.0 star property
Haines City
The price is NZ$803
includes taxes & fees
7 July - 8 July
Golf, Dine & Unwind Poolside! Haines City Getaway
Interior

Beautiful Historic Cottage, Rendezvous

Beautiful Historic Cottage, Rendezvous
Mount Dora
9.4 out of 10, Exceptional, (16 reviews)
"This property is the perfect location for walking downtown shops and dining! "
United States
Julie
The price is NZ$355
includes taxes & fees
13 July - 14 July
Beautiful Historic Cottage, Rendezvous
Property grounds

Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is NZ$374
includes taxes & fees
2 July - 3 July
Romantic Lakefront Getaway with Balcony near Downtown Orlando
Front of property

Mount Dora Cottages

Mount Dora Cottages
3.0 star property
Mount Dora
9.4 out of 10, Exceptional, (212 reviews)
"Perfect spot"
United States
PATRICIA
The price is NZ$417
includes taxes & fees
2 July - 3 July
Mount Dora Cottages
Exterior

Newly Remodeled Tiny Home 20 minutes from Disney!~

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is NZ$365
includes taxes & fees
13 July - 14 July
Newly Remodeled Tiny Home 20 minutes from Disney!~
Exterior

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema

Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
3.0 star property
Kissimmee
The price is NZ$1,620
includes taxes & fees
28 July - 29 July
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Garden Hotel Reviews

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

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

10/10 Excellent
"Loved how helpful the staff was!"
Amanda 6-night trip
Posted less than an hour ago
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
452
Accommodation
2317 Cottages
Lowest Price
NZ$277
Highest Price
NZ$1,620

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between NZ$277 and NZ$1,620 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.

Explore a world of travel with Expedia