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A river winding through a town with a bridge, surrounded by greenery and buildings.

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    Check prices for these dates

    Check prices for these dates, December 15 – 16, 2026

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    Our top choices for Maitland cottages

    1. Incredible Private Lakefront Cottage Retreat

    A deck with a table and chairs, an umbrella, and a view of a lake with trees.

    2. Downtown Cottage

    A room with a bed, a TV on a stand, a bookshelf, and a window with blinds.

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

    A white building with large windows and a brick pathway leading to it.

    4. Disney Pool Days & Hammock Naps Book Your Escape NOW!

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

    5. Romantic Lakefront Getaway with Balcony near Downtown Orlando

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

    6. Orlando Getaway? 🌴 Private Lanai & Cozy Cottage

    A landscaped backyard with a wooden fence, gravel ground, and outdoor lighting.

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

    A bench in a park with a lake and trees in the background.

    8. Th130 - 3BR House Near Disney and Universal Parks

    A resort with multiple swimming pools, palm trees, and a large building with a red-tiled roof.

    9. Historic Tremain Cottages

    A covered porch with wicker chairs and a ceiling fan.

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

    A lakeside patio with wooden rocking chairs and a table, overlooking a calm lake and a forested area.

    11. Beautiful Historic Cottage, Nantucket

    A wooden deck with a table and chairs, a white building with large windows, and a wooden fence.

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

    A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

    13. Beautiful Historic Cottage, The Garden

    A covered porch with white wicker furniture and green cushions, large windows, and a ceiling fan.

    14. Beautiful Historic Cottage, Rendezvous

    A hallway with a dining area, a black metal chair, and a sign reading "Rendezvous".

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

    A resort with multiple swimming pools, palm trees, and a large building with a red-tiled roof.

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

    A resort with multiple swimming pools, palm trees, and a large building with a red-tiled roof.

    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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    Learn more about Maitland

    Stroll along the boardwalk at Lake Lily Park where weekend farmers markets showcase local treats and artisan crafts. Art lovers shouldn't miss the Maitland Art Center's Mayan-inspired architecture and rotating exhibits, while paddlers can explore peaceful waterways connecting the city's chain of lakes.

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    A river winding through a town with a bridge, surrounded by greenery and buildings.

    Frequently Asked Questions

    How much do cottages in Maitland cost?

    Rates for cottages in Maitland range between $168 and $511 per night. Whatever your budget, you're sure to find the perfect place to get in tune 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 Maitland with Expedia?

    We think that a vacation should be a breeze, so if you're chasing cottages in Maitland at the perfect price, Expedia delivers. Stick to the budget and go for a low-cost option far from the downtown buzz, or splurge on an upmarket cottage to pamper your favorite people.

    How can I find cheap cottages in Maitland?

    A great way to get cheap cottages in Maitland is with Expedia's convenient filter tool. Refine your search results by star rating, amenities and budget to grab awesome rates in just a few clicks.

    What is there to do in Maitland near my cottage?

    There are plenty of wonderful things to do in Maitland. Don't miss major attractions like Maitland Historical Society, Maitland Art Center and Lake Lily Park. Maitland Community Park, Lil 500 Go-Karts and Enzian Theater are also on many to-do lists.

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