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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

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 £408
includes taxes & fees
14 Jul - 15 Jul
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 £123
includes taxes & fees
13 Jul - 14 Jul
Historic Tremain Cottages
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
The price is £394
includes taxes & fees
29 Jul - 30 Jul
Chic Orlando Family Getaway w/ Fenced Yard!
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 £177
includes taxes & fees
13 Jul - 14 Jul
Mount Dora 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, (61 reviews)
"Such a cute and clean rental! Well stocked coffee bar and the beds were so comfy after a long day. Quiet nice neighborhood, and host was quick to respond to questions. Left thoughtful touches throughout the space. 10/10 would recommend!"
United States
Christine N.
The price is £184
includes taxes & fees
15 Jul - 16 Jul
Pool Days & Hammock Naps Book Your Escape Before It’s Gone
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 £223
includes taxes & fees
13 Jul - 14 Jul
Cozy Lake Front Cottage
House (6 Bedrooms) | Interior

Upstay Spacious Home w Private Pool & Hot Tub

Upstay Spacious Home w Private Pool & Hot Tub
3.0 star property
Solana
The price is £341
includes taxes & fees
13 Jul - 14 Jul
Upstay Spacious Home w Private Pool & Hot Tub
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 £261
includes taxes & fees
11 Aug - 12 Aug
Incredible Private Lakefront Cottage Retreat
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 £156
includes taxes & fees
13 Jul - 14 Jul
Beautiful Historic Cottage, Rendezvous
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 £138
includes taxes & fees
15 Jul - 16 Jul
Downtown Cottage
Terrace/patio

Beautiful Historic Cottage, The Garden

Beautiful Historic Cottage, The Garden
Mount Dora
10.0 out of 10, Exceptional, (15 reviews)
"It was a perfect house for our short stay. Great location."
United States
Connie D.
The price is £162
includes taxes & fees
14 Jul - 15 Jul
Beautiful Historic Cottage, The Garden
Terrace/patio

Last-Minute Deal! Crystal Springs Adventure Awaits

Last-Minute Deal! Crystal Springs Adventure Awaits
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 £179
includes taxes & fees
13 Jul - 14 Jul
Last-Minute Deal! Crystal Springs Adventure Awaits
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 £340
includes taxes & fees
18 Jul - 19 Jul
Golf, Dine & Unwind Poolside! Haines City 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, (21 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 £192
includes taxes & fees
3 Aug - 4 Aug
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
10.0 out of 10, Exceptional, (43 reviews)
"The place was great overall, had everything needed. Rooms and bathrooms were spacious. Hosts left goodies for the stay, communicated what was needed, and made the check-in/check-out process very easy. Would stay again. It was perfect distance from Kia Center (5 min drive) "
United States
M L.
The price is £257
includes taxes & fees
13 Jul - 14 Jul
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 £637
includes taxes & fees
11 Aug - 12 Aug
Serenity Lakeview Retreat Stunning Water Views, No Rear Neighbors, Private Pool, Game Room & Star Wars Cinema
House (5 Bedrooms) | Interior

Spacious Family Home w Pool, Hot Tub & BBQ

Spacious Family Home w Pool, Hot Tub & BBQ
3.0 star property
Kissimmee
The price is £343
includes taxes & fees
14 Jul - 15 Jul
Spacious Family Home w Pool, Hot Tub & BBQ
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 £271
includes taxes & fees
14 Jul - 15 Jul
Oasis Near Disney w Golf View, Family&pet Friendly
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 £168
includes taxes & fees
25 Jul - 26 Jul
Charming Historic Cottage with Cozy Porch and Garden Retreat
Exterior

Newly Remodeled Tiny Home 20 minutes from Disney!~

Newly Remodeled Tiny Home 20 minutes from Disney!~
Kissimmee
The price is £161
includes taxes & fees
13 Jul - 14 Jul
Newly Remodeled Tiny Home 20 minutes from Disney!~
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

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

10/10 Excellent
"Amazing water park great having Starbucks on property big spacious rooms"
Julia 3-night trip
Posted 6 hours ago
The Grove Resort & Water Park Orlando

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
445
Accommodation
2561 Cottages
Lowest Price
£123
Highest Price
£637

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between £123 and £637 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 holiday 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 accommodation 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 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.