Search Winter Park Cottages

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

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
9.0 out of 10, Wonderful, (4)
"great experience. very clean and in a good area"
United States
Aubrey V.
$120 nightly
The price is $133
Nov 24 - Nov 25
Total with taxes and fees
Charming 2-bedroom Country Cottage in Kissimmee with private parking
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
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.
$223 nightly
The price is $246
Nov 22 - Nov 23
Total with taxes and fees
Cozy Cottage Retreat – Queen Bed, Fire Pit & Private Lanai
Exterior
The Blue Loft-Cozy Style Guest House · Close to UCF, Downtown & Theme Parks

The Blue Loft-Cozy Style Guest House · Close to UCF, Downtown & Theme Parks

2.0 star property
Orlando
$134 nightly
The price is $148
Nov 19 - Nov 20
Total with taxes and fees
The Blue Loft-Cozy Style Guest House · Close to UCF, Downtown & Theme Parks
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.
Guesthouse Retreat – Private Pool & King Suite
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.
$290 nightly
The price is $320
Nov 17 - Nov 18
Total with taxes and fees
Hidden Garden Cottage-Swim&Spa, Ctrl Orlando Disney Universal Sea World Beaches,
Interior
Tiny Hidden Cottage

Tiny Hidden Cottage

Longwood
9.2 out of 10, Wonderful, (56)
"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 16 - Nov 17
Total with taxes and fees
Tiny Hidden Cottage
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 15 - Nov 16
Total with taxes and fees
Cozy Deltona Stay Fire Pit + Orlando
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 16 - Nov 17
Total with taxes and fees
Fire Pit & Yard: Updated Winter Garden Home!
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, (29)
"Easy and convenient in a nice place "
United States
cameron h.
$343 nightly
The price is $380
Nov 17 - Nov 18
Total with taxes and fees
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
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.
$292 nightly
The price is $323
Nov 23 - Nov 24
Total with taxes and fees
Incredible Private Lakefront Cottage Retreat
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 Park Hotel Reviews

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"👍"
CHAD 1-night trip
Posted 11 hours ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Find out more about Winter Park

Winter Park Cottages information

Number of reviews
201
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.

Explore a world of travel with Expedia