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Search Cottages in Winter Springs

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Compare 90 Cottages in Winter Springs with updated reviews, rates, and availability.

Orlando Lakefront Tiny House Community
Exterior

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (221)
"The location was beautiful. Loved the outside bed and being able to use the kayaks free of charge. Would be nice to have a few more in case our whole group wanted to go out. (6 of us) I did not ask as there may have been more if we asked. Overall, it was very nice and I would definitely stay again. Communication was great. Never had to wait for anything. However, the dryer did not work, and the one bedroom door did not close properly or lock. (not the king bedroom) Also, it would have been...
The price is AED 289
AED 585 total
includes taxes & fees
1 Dec - 2 Dec
Orlando Lakefront Tiny House Community
Downtown Winter Garden Cottage ~ 12 Mi to Disney!
Winter Garden Vacation Rental | 2BR | 1BA | 3 Steps Required for Entry

Downtown Winter Garden Cottage ~ 12 Mi to Disney!

9.8 out of 10, Exceptional, (41)
"Very comfortable beds. Kitchen well equipped. Nice front porch to sit on. Walking distance to shops & restaurants in downtown Winter Garden. Would definitely recommend."
Downtown Winter Garden Cottage ~ 12 Mi to Disney!
Tiny Hidden Cottage
Room

Tiny Hidden Cottage

9.4 out of 10, Exceptional, (23)
"COZY & CLEAN. GREAT PLACE FOR A COUPLE TO GET AWAY FOR A WEEKEND. CLEAN& COMFORTABLE."
The price is AED 338
AED 616 total
includes taxes & fees
25 Nov - 26 Nov
Tiny Hidden Cottage
Downtown Winter Garden Home ~ 12 Mi to Disney!
Winter Garden Vacation Rental | 3BR | 2BA | 1,200 Sq Ft | 3 Steps to Enter

Downtown Winter Garden Home ~ 12 Mi to Disney!

9.6 out of 10, Exceptional, (5)
"We evacuated from Helene. Because we were unable to return to our home, we ended up having to rent multiple vacation rentals. This is the first home that actually looked like it did online--really lovely. (I agree, yard can use some TLC) I liked the retro touches throughout. Comfortable furniture and beds. Luxury towels and linens. Really nice! Walk west and cross over Dillard two block then three blocks north to Plant street and you'll find many wonderful restaurants and shops. Saturday...
Downtown Winter Garden Home ~ 12 Mi to Disney!
4801 Tidecrest Avenue #166
Living area

4801 Tidecrest Avenue #166

3.0 star property
The price is AED 1,785
AED 2,959 total
includes taxes & fees
25 Dec - 26 Dec
4801 Tidecrest Avenue #166
Weekday special! Guest House with Private pool & WiFi
Pool

Weekday special! Guest House with Private pool & WiFi

9.8 out of 10, Exceptional, (26)
"I had surgery and stayed here for my recovery, nice quiet area, easily accessible to stores and very comfortable bed. I felt very comfortable while recuperating. Washer and dryer big plus and the pool was beautiful and well kept. I didn't get to use the pool but I sure would have loved to. I will be back when I have to go for my checkups "
The price is AED 459
AED 1,023 total
includes taxes & fees
16 Dec - 17 Dec
Weekday special! Guest House with Private pool & WiFi
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Orlando oasis ☀️

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

9.8 out of 10, Exceptional, (6)
"Our family of 4 (myself, my husband and my parents) along with our little pup enjoyed our stay. The property was clean and the availability of snacks and a stocked bar was an added bonus. I wish we could've stayed longer. Highly recommend!"
The price is AED 477
AED 1,068 total
includes taxes & fees
9 Dec - 10 Dec
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
Resort Townhome: Perfect Orlando Vacation Spot!!
Living area

Resort Townhome: Perfect Orlando Vacation Spot!!

4.0 star property
8.0 out of 10, Very Good, (1)
Resort Townhome: Perfect Orlando Vacation Spot!!
Orlando Golden Girls Retreat: Prime Location!
Living area

Orlando Golden Girls Retreat: Prime Location!

3.0 star property
Orlando Golden Girls Retreat: Prime Location!
Chic Orlando Family Getaway w/ Fenced Yard!
Living area

Chic Orlando Family Getaway w/ Fenced Yard!

3.0 star property
10.0 out of 10, Exceptional, (1)
Chic Orlando Family Getaway w/ Fenced Yard!
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
Pool

Orlando Home w/ Private Pool: 10 Mi to UCF Campus!

3.0 star property
Orlando Home w/ Private Pool: 10 Mi to UCF Campus!
Florida Vacation Rental on < 6 Acres w/ Fire Pit!
Living area

Florida Vacation Rental on < 6 Acres w/ Fire Pit!

3.0 star property
Florida Vacation Rental on < 6 Acres w/ Fire Pit!
Orlando Honeymoon Cottage with queen bed & fire pit.
Fire Pit

Orlando Honeymoon Cottage with queen bed & fire pit.

10.0 out of 10, Exceptional, (7)
"Nice and clean, and small"
The price is AED 386
AED 929 total
includes taxes & fees
2 Dec - 3 Dec
Orlando Honeymoon Cottage with queen bed & fire pit.
The Pink Door Cottage-Historic Sanford
Exterior detail

The Pink Door Cottage-Historic Sanford

10.0 out of 10, Exceptional, (9)
"A great location in Sanford. Well-stocked house in a historic district near downtown. Close to everything. Great host. Sleeps six comfortably. Large backyard with outdoor patio and bbq. An excellent family unit. 5 stars +."
The Pink Door Cottage-Historic Sanford
Deltona Lake House, Day Trip to Disney & Universal
Exterior

Deltona Lake House, Day Trip to Disney & Universal

3.0 star property
10.0 out of 10, Exceptional, (2)
"This house was perfect! Very spacious, clean, and felt like a very safe neighborhood for a few women traveling. The ONLY improvements I would suggest would be having more towels, and extra blankets available for guests. And I would replace the pull out couch mattress as it was very uncomfortable. Still a 10/10 overall!"
Deltona Lake House, Day Trip to Disney & Universal
Apopka Single-story Home w/ Private Lanai + Pool!
Pool

Apopka Single-story Home w/ Private Lanai + Pool!

3.0 star property
Apopka Single-story Home w/ Private Lanai + Pool!
Altamonte Springs Home w/ Canoe on Lake Marion
Living area

Altamonte Springs Home w/ Canoe on Lake Marion

3.0 star property
Altamonte Springs Home w/ Canoe on Lake Marion
Sandford Vacation Rental Near Airport & Lake!
Outdoor dining

Sandford Vacation Rental Near Airport & Lake!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house and location for our business trip was perfect. The house was spacious, clean, and had everything we needed. Communication with the owner was excellent and he was very accommodating. We plan on renting this house again for our next pet trip to the area "
Sandford Vacation Rental Near Airport & Lake!
Relaxing 2-bedroom cottage in beautiful Sanford
Living area

Relaxing 2-bedroom cottage in beautiful Sanford

Relaxing 2-bedroom cottage in beautiful Sanford
Lakefront - Lake Davis Art Deco Cottage
Living area

Lakefront - Lake Davis Art Deco Cottage

10.0 out of 10, Exceptional, (4)
"The cottage was even more impressive than we anticipated. The rooms were all attractive and very clean. My husband and I loved the location and took advantage of our surroundings.We walked several miles a day (weather permitting)around the nearby lakes. We found local eateries, went to Sunday farmers’ market and simply relaxed sitting out on the front lawn. The owner, Jeff and his manager, Becky made sure we were happy and comfortable. We are so happy that we found this perfect winter getaway!"
Lakefront - Lake Davis Art Deco Cottage
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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Other property types in Winter Springs

The View Studio Suites and Event Venue
Front of property

The View Studio Suites and Event Venue

3.5 star property
8.6 out of 10, Excellent, (565)
"They are remodeling the building but is nice and for the price..and the breakfast is a plus"
The price is AED 303
AED 331 total
includes taxes & fees
25 Nov - 26 Nov
The View Studio Suites and Event Venue
The Point Hotel & Suites
Exterior

The Point Hotel & Suites

3.5 star property
8.0 out of 10, Very Good, (3097)
"The people next to us were not pleasant..breakfast was quite a joke for what was paid and the lady running it was really rude. "
The price is AED 337
AED 412 total
includes taxes & fees
10 Dec - 11 Dec
The Point Hotel & Suites
Orlando Lakefront Tiny House Community
Exterior

Orlando Lakefront Tiny House Community

3.0 star property
9.4 out of 10, Exceptional, (221)
"The location was beautiful. Loved the outside bed and being able to use the kayaks free of charge. Would be nice to have a few more in case our whole group wanted to go out. (6 of us) I did not ask as there may have been more if we asked. Overall, it was very nice and I would definitely stay again. Communication was great. Never had to wait for anything. However, the dryer did not work, and the one bedroom door did not close properly or lock. (not the king bedroom) Also, it would have been...
The price is AED 289
AED 585 total
includes taxes & fees
1 Dec - 2 Dec
Orlando Lakefront Tiny House Community
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.

Frequently asked questions

How much do cottages in Winter Springs cost?
You can expect to pay between AED 289 and AED 1,785 per night for cottages in Winter Springs. No matter your budget, a wonderful stay is only a click away on Expedia. 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 Springs with Expedia?
We think that vacays should be stress-free, so if you’re looking for cottages in Winter Springs at an affordable rate, Expedia has got your back. Save those pennies and stay in a wallet-friendly option far away from the hustle and bustle, or splurge on an upmarket cottage to really spoil your favorite people.
How can I find cheap cottages in Winter Springs?
The simplest way to locate cheap cottages in Winter Springs is with Expedia’s handy filter tool. Narrow your search results by budget, star rating and amenities to discover awesome rates with only a few clicks.