A greenhouse with hanging flower baskets and ivy-covered walls.

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Our top choices for Longwood cottages

1. Orlando Pool Days & Hammock Naps Book Your Escape NOW!

Orlando Pool Days & Hammock Naps Book Your Escape NOW!
Lake Mary
9.8 out of 10, Exceptional, (70 reviews)
"The Property was very clean ! Super convenient location and the perfect size for a family with 2 younger children ! Suzy was super nice !"
United States
Gary
The price is CA $154
CA $356 total
includes taxes & fees
Dec 2 - Dec 3
Orlando Pool Days & Hammock Naps Book Your Escape NOW!

2. Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (23 reviews)
"We had an amazing stay! The place was beautiful, cozy, and incredibly comfortable. Even though we had to leave earlier than planned, we truly enjoyed our time here. The host was kind, responsive, and made everything easy from start to finish. We would definitely stay here again and look forward to returning in the future. Highly recommend!"
United States
Chiann M.
The price is CA $148
CA $348 total
includes taxes & fees
Dec 6 - Dec 7
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage

3. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (18 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is CA $96
CA $244 total
includes taxes & fees
Nov 11 - Nov 12
Downtown Cottage

4. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
10.0 out of 10, Exceptional, (1 review)
"Cozy and nice place. It was very clean. Comunication with host was easy. Great view and sitting area from balcony to the lake. Very relaxing!"
United States
jacqueline M.
The price is CA $127
CA $290 total
includes taxes & fees
Nov 30 - Dec 1
Romantic Lakefront Getaway with Balcony near Downtown Orlando

5. 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, (56 reviews)
"Great location, well stocked and beds were very comfortable."
United States
Raegan S.
The price is CA $251
CA $479 total
includes taxes & fees
Nov 16 - Nov 17
The Coach House- Entire Home - 2 bedroom/3 bath - Orlando Getaway!

6. The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
Lake Helen
9.8 out of 10, Exceptional, (44 reviews)
"My stay was convenient and easy. The place was clean. I will stay again!"
United States
Stacy S.
The price is CA $114
CA $185 total
includes taxes & fees
Nov 18 - Nov 19
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.

7. Shore Steps Cottage - Walking Distance To The Town Of Windermere

Shore Steps Cottage - Walking Distance To The Town Of Windermere
Windermere
10.0 out of 10, Exceptional, (1 review)
The price is CA $151
CA $439 total
includes taxes & fees
Nov 17 - Nov 18
Shore Steps Cottage - Walking Distance To The Town Of Windermere

8. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (44 reviews)
"Lovely stay in Mount Dora, perfect location, clean and quiet. Would definitely stay again."
United States
Charlotte
The price is CA $305
CA $339 total
includes taxes & fees
Dec 3 - Dec 4
Historic Tremain Cottages

9. Th20 - 3BR House With Resort Access Near Parks

Th20 - 3BR House With Resort Access Near Parks
3.0 star property
Orlando
The price is CA $325
CA $666 total
includes taxes & fees
Nov 28 - Nov 29
Th20 - 3BR House With Resort Access Near Parks

10. 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, (26 reviews)
"Great stay! Very welcoming home and very comfortable beds. Would rent again."
United States
Thomas K.
The price is CA $202
CA $352 total
includes taxes & fees
Nov 16 - Nov 17
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"

11. Beautiful Historic Cottage, Nantucket

Beautiful Historic Cottage, Nantucket
Mount Dora
9.8 out of 10, Exceptional, (8 reviews)
"Great location. Very clean "
United States
University Sports M.
The price is CA $289
CA $333 total
includes taxes & fees
Nov 11 - Nov 12
Beautiful Historic Cottage, Nantucket

12. Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is CA $281
CA $705 total
includes taxes & fees
Nov 11 - Nov 12
Fire Pit & Yard: Updated Winter Garden Home!

13. Beautiful Historic Cottage, The Garden

Beautiful Historic Cottage, The Garden
Mount Dora
10.0 out of 10, Exceptional, (15 reviews)
"Nice and quiet place to stay."
United States
Mark
The price is CA $362
CA $415 total
includes taxes & fees
Nov 11 - Nov 12
Beautiful Historic Cottage, The Garden

14. Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Orlando
The price is CA $154
CA $319 total
includes taxes & fees
Nov 11 - Nov 12
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio

15. The Ingram * 3 min walk to Downtown Mt. Dora!!

The Ingram * 3 min walk to Downtown Mt. Dora!!
Mt Dora
9.8 out of 10, Exceptional, (53 reviews)
"Perfect spot. House was decorated beautifully. Loved our stay!"
United States
Mark M.
The price is CA $377
CA $615 total
includes taxes & fees
Nov 14 - Nov 15
The Ingram * 3 min walk to Downtown Mt. Dora!!

16. Beautiful Historic Cottage, Rendezvous

Beautiful Historic Cottage, Rendezvous
Mount Dora
9.4 out of 10, Exceptional, (18 reviews)
"This property is the perfect location for walking downtown shops and dining! "
United States
Julie
The price is CA $289
CA $333 total
includes taxes & fees
Nov 11 - Nov 12
Beautiful Historic Cottage, Rendezvous

17. Th89 - 3BR House Near Disney With Resort Access

Th89 - 3BR House Near Disney With Resort Access
3.0 star property
Orlando
The price is CA $332
CA $674 total
includes taxes & fees
Dec 5 - Dec 6
Th89 - 3BR House Near Disney With Resort Access
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 Longwood Hotel Reviews

Find out more about Longwood

Longwood Cottages information

Number of reviews
378
Accommodation
219 Cottages
Lowest Price
CA $185
Highest Price
CA $834

Frequently asked questions

How much do cottages in Longwood cost?
Prices for cottages in Longwood range between CA $185 and CA $834 per night. No matter your budget, you'll find a perfect place to reconnect with nature. 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 Longwood with Expedia?
Expedia has some superb cottages in Longwood, so start packing for an unforgettable stay on nature's doorstep. If you're on a budget, click on how much you're willing to spend and the star rating of your property. Or, use our handy filters to search for cottages with a pool or a hot tub. We'll help you find the perfect place whatever your plans or bank balance.
How can I find cheap cottages in Longwood?
With Expedia's useful filter tool, getting your hands on cheap cottages in Longwood has never been easier. To find stays that'll make your bank balance smile, tailor your search results by amenities, star rating and budget.
What is there to do in Longwood near my cottage?
The most practical travel accessory is a well-planned to-do list. Alaqua Country Club is a great place to kick-start your exploration of Longwood.

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