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

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Longwood cottages

A single-story building with the number 297, a red door, and a bench outside.

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, (67 reviews)
"The property was very clean and the host was quick to respond to any questions."
United States
Colette T.
The price is ￥15,073
￥38,527 total
includes taxes & fees
Oct 13 - Oct 14
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A patio with outdoor furniture, a wooden deck, and a basketball hoop.

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

Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
Lake Mary
10.0 out of 10, Exceptional, (22 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is ￥12,087
￥35,027 total
includes taxes & fees
Oct 14 - Oct 15
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A house with a red door, a front porch, and a pathway leading to the entrance.

3. Downtown Cottage

Downtown Cottage
Colonialtown North
8.8 out of 10, Excellent, (15 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is ￥11,416
￥29,336 total
includes taxes & fees
Oct 11 - Oct 12
Downtown Cottage
A small house with a porch, a red door, and potted plants.

4. 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, (43 reviews)
"My stay was convenient and easy. The place was clean. I will stay again!"
United States
Stacy S.
The price is ￥12,798
￥22,002 total
includes taxes & fees
Oct 12 - Oct 13
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
A residential house with a front yard, a palm tree, and a garage.

5. 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 ￥28,896
￥87,922 total
includes taxes & fees
Nov 8 - Nov 9
Chic Orlando Family Getaway w/ Fenced Yard!
A white building with large windows and a brick pathway leading to it.

6. 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, (54 reviews)
"Everything was super clean and exactly as described. Great location and great stay!"
United States
Garrett S.
The price is ￥24,964
￥51,587 total
includes taxes & fees
Oct 12 - Oct 13
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

7. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is ￥12,640
￥31,758 total
includes taxes & fees
Nov 3 - Nov 4
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A serene landscape with a pond, trees with Spanish moss, and a palm tree.

8. 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 ￥17,491
￥51,711 total
includes taxes & fees
Oct 13 - Oct 14
Shore Steps Cottage - Walking Distance To The Town Of Windermere
A covered porch with wicker chairs and a ceiling fan.

9. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (43 reviews)
"Accommodations were comfortable, quaint space. Bed was very comfortable. Just beware the shower is very narrow and ceilings low. Not ideal for a taller or bigger person. Nice and close to the downtown area. Would stay here again."
United States
Betty
The price is ￥30,725
￥34,105 total
includes taxes & fees
Oct 14 - Oct 15
Historic Tremain Cottages
A small, single-story house with a gabled roof and a front porch.

10. 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 ￥33,680
￥37,384 total
includes taxes & fees
Oct 22 - Oct 23
Mount Dora Cottages
A well-lit garden area with a gravel pathway, decorative lights, and various plants.

11. 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, (25 reviews)
"Great stay! Very welcoming home and very comfortable beds. Would rent again."
United States
Thomas K.
The price is ￥23,463
￥40,604 total
includes taxes & fees
Oct 16 - Oct 17
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
A multi-story residential building with balconies, a lawn, and outdoor seating.

12. Th10 - 3BR House Near Disney and Universal Studios

Th10 - 3BR House Near Disney and Universal Studios
3.0 star property
Orlando
The price is ￥38,908
￥77,468 total
includes taxes & fees
Oct 28 - Oct 29
Th10 - 3BR House Near Disney and Universal Studios
A wooden deck with a table and chairs, a white building with large windows, and a wooden fence.

13. 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 ￥32,385
￥40,372 total
includes taxes & fees
Oct 27 - Oct 28
Beautiful Historic Cottage, Nantucket
A covered porch with white wicker furniture and green cushions, large windows, and a ceiling fan.

14. 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 ￥40,522
￥50,193 total
includes taxes & fees
Oct 13 - Oct 14
Beautiful Historic Cottage, The Garden
A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

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

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is ￥31,442
￥78,861 total
includes taxes & fees
Oct 18 - Oct 19
Fire Pit & Yard: Updated Winter Garden Home!
A lakeside patio with wooden rocking chairs and a table, overlooking a calm lake and a forested area.

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

Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
Orlando
The price is ￥17,222
￥37,546 total
includes taxes & fees
Oct 19 - Oct 20
Walkable Quiet Lakefront Retreat near Downtown Orlando with Private Patio
A hallway with a dining area, a black metal chair, and a sign reading "Rendezvous".

17. Beautiful Historic Cottage, Rendezvous

Beautiful Historic Cottage, Rendezvous
Mount Dora
9.4 out of 10, Exceptional, (17 reviews)
"This property is the perfect location for walking downtown shops and dining! "
United States
Julie
The price is ￥32,385
￥40,214 total
includes taxes & fees
Oct 13 - Oct 14
Beautiful Historic Cottage, Rendezvous
A resort with a large central pool, a smaller circular pool, and a fountain. There are multiple buildings with balconies and a parking lot.

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

Th20 - 3BR House With Resort Access Near Parks
3.0 star property
Orlando
The price is ￥38,315
￥76,782 total
includes taxes & fees
Oct 28 - Oct 29
Th20 - 3BR House With Resort Access Near Parks
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

Spark by Hilton Orlando near Universal

Spark by Hilton Orlando near Universal

10/10 Excellent
"poca variedad y el huevo “hervido” lo servian congelado"
Kynaisha 3-night trip
Posted 1 hour ago
Spark by Hilton Orlando near Universal

Find out more about Longwood

Longwood Cottages information

Number of reviews
443
Accommodation
220 Cottages
Lowest Price
￥22,002
Highest Price
￥87,922

Frequently asked questions

How much do cottages in Longwood cost?
Prices for cottages in Longwood range between ￥22,002 and ￥87,922 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.