An aerial view of a city with a prominent building complex, surrounded by dense greenery and a river.

Search Maitland Cottage Rentals from CA $257

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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 Maitland cottages

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

1. 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 6 - Oct 7
Downtown Cottage
A single-story building with the number 297, a red door, and a bench outside.

2. 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 CA $136
CA $343 total
includes taxes & fees
Oct 4 - Oct 5
Orlando Pool Days & Hammock Naps Book Your Escape NOW!
A white building with large windows and a brick pathway leading to it.

3. 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 $225
CA $465 total
includes taxes & fees
Oct 12 - Oct 13
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
A residential house with a front yard, a palm tree, and a garage.

4. 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 CA $260
CA $792 total
includes taxes & fees
Oct 15 - Oct 16
Chic Orlando Family Getaway w/ Fenced Yard!
A patio with outdoor furniture, a wooden deck, and a basketball hoop.

5. 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 CA $109
CA $311 total
includes taxes & fees
Oct 7 - Oct 8
Last-Minute Getaway? 🌴 Private Lanai & Cozy Cottage
A table with a potted plant and a cup of coffee, overlooking a scenic landscape.

6. Romantic Lakefront Getaway with Balcony near Downtown Orlando

Romantic Lakefront Getaway with Balcony near Downtown Orlando
Orlando
The price is CA $118
CA $292 total
includes taxes & fees
Oct 27 - Oct 28
Romantic Lakefront Getaway with Balcony near Downtown Orlando
A serene landscape with a pond, trees with Spanish moss, and a palm tree.

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 $229
CA $558 total
includes taxes & fees
Oct 4 - Oct 5
Shore Steps Cottage - Walking Distance To The Town Of Windermere
A covered porch with wicker chairs and a ceiling fan.

8. 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 resort with a large central pool, a smaller circular pool, and a fountain. There are multiple buildings with balconies and a parking lot.

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

Th130 - 3BR House Near Disney and Universal Parks
3.0 star property
Orlando
The price is CA $322
CA $666 total
includes taxes & fees
Oct 12 - Oct 13
Th130 - 3BR House Near Disney and Universal Parks
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 CA $303
CA $337 total
includes taxes & fees
Oct 5 - Oct 6
Mount Dora Cottages
A covered porch with white wicker furniture and green cushions, large windows, and a ceiling fan.

11. 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 $248
CA $310 total
includes taxes & fees
Oct 5 - Oct 6
Beautiful Historic Cottage, The Garden
A wooden deck with a table and chairs, a white building with large windows, and a wooden fence.

12. 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 $292
CA $366 total
includes taxes & fees
Oct 27 - Oct 28
Beautiful Historic Cottage, Nantucket
A hallway with a dining area, a black metal chair, and a sign reading "Rendezvous".

13. 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 $233
CA $293 total
includes taxes & fees
Oct 5 - Oct 6
Beautiful Historic Cottage, Rendezvous
A two-story house with a front porch, a brick driveway, and a well-maintained lawn.

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

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is CA $299
CA $727 total
includes taxes & fees
Oct 20 - Oct 21
Fire Pit & Yard: Updated Winter Garden Home!
A multi-story residential building with balconies, a lawn, and outdoor seating.

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

Th10 - 3BR House Near Disney and Universal Studios
3.0 star property
Orlando
The price is CA $350
CA $697 total
includes taxes & fees
Oct 28 - Oct 29
Th10 - 3BR House Near Disney and Universal Studios
A resort with a large central pool, a smaller circular pool, and a fountain. There are multiple buildings with balconies and a parking lot.

16. 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 $345
CA $691 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 Maitland Hotel Reviews

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

10/10 Excellent
"Nice"
James 1-night trip
Posted 1 hour ago
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Find out more about Maitland

Maitland Cottages information

Number of reviews
375
Accommodation
179 Cottages
Lowest Price
CA $257
Highest Price
CA $792

Frequently asked questions

How much do cottages in Maitland cost?
Rates for cottages in Maitland range between CA $257 and CA $792 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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