Kissimmee Lakefront Park Grassy waterfront park with walking paths, a fishing pier, picnic pavilions, and a shaded playground. children's playgrounds, splash pad

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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

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 CA $299
CA $760 total
includes taxes & fees
Jun 30 - Jul 1
Fire Pit & Yard: Updated Winter Garden Home!
The Garden, Pet Friendly | Terrace/patio

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 CA $206
CA $229 total
includes taxes & fees
Jun 23 - Jun 24
Historic Tremain Cottages
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 CA $107
CA $269 total
includes taxes & fees
Jun 16 - Jun 17
Downtown Cottage
Exterior

Poolside Weekday Retreat – Just 119 Night!

Poolside Weekday Retreat – Just 119 Night!
Lake Mary
9.8 out of 10, Exceptional, (54 reviews)
"Everything was wonderful! We loved the location and the house was cozy and comfortable. "
United States
Mike B.
The price is CA $175
CA $397 total
includes taxes & fees
Jun 30 - Jul 1
Poolside Weekday Retreat – Just 119 Night!
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 CA $197
CA $547 total
includes taxes & fees
Jun 16 - Jun 17
Golf, Dine & Unwind Poolside! Haines City Getaway
Exterior

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 CA $169
CA $479 total
includes taxes & fees
Jun 16 - Jun 17
Incredible Private Lakefront Cottage Retreat
Terrace/patio

Charming Cottage Retreat – Just 100 a Night Midweek Special Early Check In

Charming Cottage Retreat – Just 100 a Night Midweek Special 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 CA $126
CA $335 total
includes taxes & fees
Jun 22 - Jun 23
Charming Cottage Retreat – Just 100 a Night Midweek Special 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 CA $107
CA $282 total
includes taxes & fees
Jun 16 - Jun 17
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, (22 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 CA $188
CA $411 total
includes taxes & fees
Jun 16 - Jun 17
Cozy Lake Front Cottage
Front of property

Mount Dora Cottages

Mount Dora Cottages
3.0 star property
Mount Dora
9.4 out of 10, Exceptional, (211 reviews)
"Perfect spot"
United States
PATRICIA
The price is CA $298
CA $331 total
includes taxes & fees
Jun 17 - Jun 18
Mount Dora Cottages
Property grounds

Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
The price is CA $208
CA $531 total
includes taxes & fees
Jun 16 - Jun 17
Shore Steps Cottage - Walking Distance To The Town Of Windermere
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, (18 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.
The price is CA $191
CA $353 total
includes taxes & fees
Jun 16 - Jun 17
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
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
9.8 out of 10, Exceptional, (40 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 CA $252
CA $501 total
includes taxes & fees
Jul 13 - Jul 14
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
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 CA $330
CA $1,290 total
includes taxes & fees
Jun 17 - Jun 18
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
House (4 Bedrooms) | Interior

Pool Access! Spacious Home Near Wekiwa Springs

Pool Access! Spacious Home Near Wekiwa Springs
3.0 star property
Apopka
The price is CA $189
CA $569 total
includes taxes & fees
Jun 17 - Jun 18
Pool Access! Spacious Home Near Wekiwa Springs
Property grounds

Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is CA $140
CA $317 total
includes taxes & fees
Jun 18 - Jun 19
Romantic Lakefront Getaway with Balcony near Downtown Orlando
House (3 Bedrooms) | Interior

Oasis Near Disney w Golf View, Family&pet Friendly

Oasis Near Disney w Golf View, Family&pet Friendly
3.0 star property
Reunion
The price is CA $125
CA $512 total
includes taxes & fees
Jun 19 - Jun 20
Oasis Near Disney w Golf View, Family&pet Friendly
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 CA $99
CA $218 total
includes taxes & fees
Jun 16 - Jun 17
Cozy Forest Retreat Mid-Century Charm Fireplace 20 Min to Disney
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 CA $229
CA $285 total
includes taxes & fees
Jun 16 - Jun 17
Beautiful Historic Cottage, Rendezvous
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 CA $224
CA $547 total
includes taxes & fees
Jul 12 - Jul 13
Family Resort Home w Pool, BBQ & Game Room
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

8/10 Good
"Everything was great."
Joaquin 4-night trip
Posted 1 hour ago
Home2 Suites by Hilton Orlando at Flamingo Crossings

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
459
Accommodation
2549 Cottages
Lowest Price
CA $218
Highest Price
CA $1,290

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between CA $218 and CA $1,290 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.
Why book your cottage in Winter Garden with Expedia?
Expedia has some great cottages in Winter Garden, so get ready for a memorable vacation on nature's doorstep. If you're sticking to a budget, select how much you'd like to spend and the preferred star rating of your property. Or, use our filters to search for cottages with free WiFi or a kitchen. We'll help you find the right fit whatever your bank balance or plans.
How can I find cheap cottages in Winter Garden?
With Expedia's convenient filter tool, scoring cheap cottages in Winter Garden has never been simpler. To discover accommodations that'll make your wallet happy, fine-tune your search results by budget, star rating and amenities.
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 travelers' 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.

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