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

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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, (66 reviews)
"The property was very clean and the host was quick to respond to any questions."
United States
Colette T.
The price is CA $147
CA $358 total
includes taxes & fees
Oct 3 - Oct 4
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, (21 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is CA $134
CA $343 total
includes taxes & fees
Oct 7 - Oct 8
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 CA $97
CA $257 total
includes taxes & fees
Oct 4 - Oct 5
Downtown Cottage
A white building with large windows and a brick pathway leading to it.

4. 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 CA $224
CA $463 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.

5. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is CA $120
CA $294 total
includes taxes & fees
Oct 5 - Oct 6
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A covered porch with wicker chairs and a ceiling fan.

6. 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 CA $231
CA $257 total
includes taxes & fees
Oct 6 - Oct 7
Historic Tremain Cottages
A small house with a porch, a red door, and potted plants.

7. 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 CA $115
CA $198 total
includes taxes & fees
Oct 12 - Oct 13
The Hidden Gem in historic Lake Helen. Next to Cassadaga & downtown Deland.
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 CA $229
CA $558 total
includes taxes & fees
Oct 2 - Oct 3
Shore Steps Cottage - Walking Distance To The Town Of Windermere
A well-lit garden area with a gravel pathway, decorative lights, and various plants.

9. 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 CA $203
CA $370 total
includes taxes & fees
Oct 11 - Oct 12
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

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

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is CA $298
CA $726 total
includes taxes & fees
Oct 2 - Oct 3
Fire Pit & Yard: Updated Winter Garden Home!
A hallway with a dining area, a black metal chair, and a sign reading "Rendezvous".

11. 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 CA $232
CA $289 total
includes taxes & fees
Oct 6 - Oct 7
Beautiful Historic Cottage, Rendezvous
A covered porch with white wicker furniture and green cushions, large windows, and a ceiling fan.

12. Beautiful Historic Cottage, The Garden

Beautiful Historic Cottage, The Garden
Mount Dora
10.0 out of 10, Exceptional, (15 reviews)
"It was a perfect house for our short stay. Great location."
United States
Connie D.
The price is CA $247
CA $307 total
includes taxes & fees
Oct 6 - Oct 7
Beautiful Historic Cottage, The Garden
A small, single-story house with a gabled roof and a front porch.

13. 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 CA $303
CA $336 total
includes taxes & fees
Oct 5 - Oct 6
Mount Dora Cottages
A wooden deck with a table and chairs, a white building with large windows, and a wooden fence.

14. 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 $291
CA $365 total
includes taxes & fees
Oct 27 - Oct 28
Beautiful Historic Cottage, Nantucket
A single-story house with a front porch, a flag, and a small garden area.

15. Mount Dora Home: Private Pool, Spa & Tropical Bar!

Mount Dora Home: Private Pool, Spa & Tropical Bar!
3.0 star property
Mount Dora
6.0 out of 10, (1 review)
The price is CA $219
CA $483 total
includes taxes & fees
Oct 5 - Oct 6
Mount Dora Home: Private Pool, Spa & Tropical Bar!
A wooden pier extending into a body of water with a bench at the end.

16. Waterfront Lake Dora Escape w/ Private Dock & Slip

Waterfront Lake Dora Escape w/ Private Dock & Slip
3.0 star property
Tavares
Waterfront Lake Dora Escape w/ Private Dock & Slip
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
"Clean room but AC seemed off a little. Humidity in the room seemed high. I guess that’s Florida for you."
Kathy 1-night trip
Posted 1 hour ago
Spark by Hilton Orlando near Universal

Find out more about Longwood

Longwood Cottages information

Number of reviews
461
Accommodation
220 Cottages
Lowest Price
CA $198
Highest Price
CA $726

Frequently asked questions

How much do cottages in Longwood cost?
Prices for cottages in Longwood range between CA $198 and CA $726 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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