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Cottages in Winter Park

Exterior
Charming 2-bedroom Country Cottage in Kissimmee with private parking

Charming 2-bedroom Country Cottage in Kissimmee with private parking

Kissimmee
10.0 out of 10, Exceptional, (3)
"great experience. very clean and in a good area"
United States
Aubrey V.
$120 nightly
The price is $133
Nov 17 - Nov 18
Total with taxes and fees
Charming 2-bedroom Country Cottage in Kissimmee with private parking
Exterior
Guesthouse Retreat – Private Pool & King Suite

Guesthouse Retreat – Private Pool & King Suite

Lake Mary
9.8 out of 10, Exceptional, (42)
"Great times!!! I would book again!!!"
United States
Darren B.
$233 nightly
The price is $257
Nov 14 - Nov 15
Total with taxes and fees
Guesthouse Retreat – Private Pool & King Suite
Property grounds
Cozy Cottage Retreat – Queen Bed, Fire Pit & Private Lanai

Cozy Cottage Retreat – Queen Bed, Fire Pit & Private Lanai

Lake Mary
10.0 out of 10, Exceptional, (16)
"Great place and exactly as described. "
United States
Kanzeda C.
$235 nightly
The price is $260
Nov 22 - Nov 23
Total with taxes and fees
Cozy Cottage Retreat – Queen Bed, Fire Pit & Private Lanai
Interior
Tiny Hidden Cottage

Tiny Hidden Cottage

Longwood
9.2 out of 10, Wonderful, (55)
"The house is perfect for my weekend trips to the area and I plan to stay there again if my travels permit. "
United States
Wesley P.
$131 nightly
The price is $144
Nov 9 - Nov 10
Total with taxes and fees
Tiny Hidden Cottage
1 bedroom, desk, WiFi, bed sheets
The Sanford Foodie Guest House

The Sanford Foodie Guest House

Sanford
8.8 out of 10, Excellent, (13)
"Cozy little place to stay"
United States
Ruth P.
$134 nightly
The price is $148
Nov 30 - Dec 1
Total with taxes and fees
The Sanford Foodie Guest House
Fridge, microwave, oven, stovetop
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,

Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,

Altamonte Springs
8.6 out of 10, Excellent, (16)
"Lots of room to spend time with family and friends. Great location, easy to move around Orlando from here."
United States
Rachael C.
$285 nightly
The price is $315
Nov 17 - Nov 18
Total with taxes and fees
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Exterior
Cozy Deltona Stay Fire Pit + Orlando

Cozy Deltona Stay Fire Pit + Orlando

2.0 star property
Deltona Lakes
$282 nightly
The price is $314
Nov 8 - Nov 9
Total with taxes and fees
Cozy Deltona Stay Fire Pit + Orlando
Exterior
Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat

Altamonte Springs
10.0 out of 10, Exceptional, (27)
"Super cool spot I sank in the main bed in bedroom Aside from that the place was amazing"
United States
Chris W.
$332 nightly
The price is $368
Nov 23 - Nov 24
Total with taxes and fees
Incredible Private Lakefront Cottage Retreat
Smart TV, DVD player
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, (29)
"Easy and convenient in a nice place "
United States
cameron h.
$345 nightly
The price is $382
Nov 10 - Nov 11
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
House (2 Bedrooms) | Interior
Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!

3.0 star property
Winter Garden
$426 nightly
The price is $476
Nov 9 - Nov 10
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
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 Park Hotel Reviews

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"Amazing place in Orlando for te family "
Crystal 1-night trip
Posted 12 hours ago
Universal's Cabana Bay Beach Resort

Find out more about Winter Park

Winter Park Cottages information

Number of reviews
200
Accommodation
262 Cottages
Lowest Price
$133
Highest Price
$476

Frequently asked questions

How much do cottages in Winter Park cost?
Cottages in Winter Park range between $133 and $476 per night. These stays offer a chance to touch base 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 Park with Expedia?
Expedia has some terrific cottages in Winter Park, so start packing for a memorable vacation close to nature. If you have a fixed budget, choose how much you'd like to spend and the preferred star rating of your property. Or, make use of our filters to search for cottages with a pool or a kitchen. We'll help you find the perfect fit whatever your plans or bank balance.
How can I find cheap cottages in Winter Park?
Expedia is here to help you easily track down cheap cottages in Winter Park. To discover your dream stay in a couple of quick clicks, simply use our handy filter tool to tailor your search results by amenities, star rating and budget.
What is there to do in Winter Park near my cottage?
There are tons of superb things to sink your teeth into in Winter Park. Discover well-known attractions like Winter Park Country Club, Crealde School of Art and Winter Park Village. Casa Feliz Historic Home Museum, Albin Polasek Museum and Sculpture Gardens and Kraft Azalea Gardens are other must-see's.

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