Best Cottages in Longwood in 2026

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

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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!

Lake Mary

Colette T.

includes taxes & fees

3 Oct - 4 Oct

A patio with outdoor furniture, a wooden deck, and a basketball hoop.

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

Lake Mary

Tricia S.

includes taxes & fees

7 Oct - 8 Oct

A house with a red door, a front porch, and a pathway leading to the entrance.

3. Downtown Cottage

Colonialtown North

Jerred B.

includes taxes & fees

4 Oct - 5 Oct

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!

College Park

Garrett S.

includes taxes & fees

12 Oct - 13 Oct

A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

5. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Orlando

includes taxes & fees

5 Oct - 6 Oct

A covered porch with wicker chairs and a ceiling fan.

6. Historic Tremain Cottages

Mount Dora

Betty

includes taxes & fees

6 Oct - 7 Oct

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.

Lake Helen

Stacy S.

includes taxes & fees

5 Oct - 6 Oct

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

Windermere

includes taxes & fees

2 Oct - 3 Oct

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Top Longwood Hotel Reviews

Avanti International Resort

10/10 Excellent

"Was a good experience"

Rosen Inn at Pointe Orlando

10/10 Excellent

"Have stayed here many times over the years. Stayed at the Rosen closest to Universal for 3 nights before coming back to here for the end of our holiday and i can honestly say that this hotel is streets ahead of that in terms of cleanliness and size of toilet and room also a lot brighter. This hotel has been well and truly brightened up with lighter paint in rooms and brighter white bulbs everywhere which really does make a difference. At check in i requested block G high up and it was no issue. Yes you will get some noise from the I4 but as it's so busy any of the hotels will that are near it. No complaints here and we look forward to being back next year."

Ramada by Wyndham Suites Orlando Airport

10/10 Excellent

"Building and room were exceptionally clean and well cared for. The pool was a wonderful addition, our kids enjoyed swimming during our short stay. Breakfast was perfect before our flight. Staff was incredibly attentive, friendly and took pride in keeping the shared spaces cleaned."

Find out more about Longwood

Longwood Cottages information

Number of reviews	461
Accommodation	220 Cottages
Lowest Price	£108
Highest Price	£386

Frequently asked questions

How much do cottages in Longwood cost?

Prices for cottages in Longwood range between £108 and £386 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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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Longwood cottages

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