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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Leesburg cottages

A white house with a covered porch, surrounded by lush greenery and a large tree.

1. Waterfront Cottage on Haynes Creek

Waterfront Cottage on Haynes Creek
Leesburg
9.4 out of 10, Exceptional, (21 reviews)
"Cute little cottage, we had a nice relaxing stay."
United States
Rebecca S.
The price is ￥14,079
￥30,836 total
includes taxes & fees
Nov 11 - Nov 12
Waterfront Cottage on Haynes Creek
A covered outdoor area with a pool, palm trees, and a tiled floor.

2. The Villages 2BR Vacation Home, Lanai & Golf Cart

The Villages 2BR Vacation Home, Lanai & Golf Cart
3.0 star property
Belvedere
10.0 out of 10, Exceptional, (5 reviews)
"Great place to stay!! Nice home, quiet street, and better than staying in a hotel."
United States
Paul
The price is ￥15,485
￥52,763 total
includes taxes & fees
Nov 24 - Nov 25
The Villages 2BR Vacation Home, Lanai & Golf Cart
A covered outdoor area with a vehicle and a boat, surrounded by trees and a white fence.

3. Cozy 1-bedroom cottage in Lake Panasoffkee with boat parking

Cozy 1-bedroom cottage in Lake Panasoffkee with boat parking
Lake Panasoffkee
The price is ￥11,235
￥22,372 total
includes taxes & fees
Nov 11 - Nov 12
Cozy 1-bedroom cottage in Lake Panasoffkee with boat parking
A covered porch with wicker chairs and a ceiling fan.

4. Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (44 reviews)
"Lovely stay in Mount Dora, perfect location, clean and quiet. Would definitely stay again."
United States
Charlotte
The price is ￥33,835
￥37,557 total
includes taxes & fees
Nov 11 - Nov 12
Historic Tremain Cottages
A beachside restaurant named Gator Joes with a wooden boardwalk leading to the entrance.

5. Cozy Cottage At Lake Weir

Cozy Cottage At Lake Weir
Ocklawaha
10.0 out of 10, Exceptional, (14 reviews)
"My daughters and granddaughter stayed for three nights and we had blast. We loved the cozy cottage. It was clean, nicely decorated and there were even snacks and cold drinks upon arrival. We definitely will stay again."
United States
Tracey
The price is ￥19,514
￥34,699 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Cottage At Lake Weir
A well-lit garden area with a gravel pathway, decorative lights, and various plants.

6. 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, (26 reviews)
"Great stay! Very welcoming home and very comfortable beds. Would rent again."
United States
Thomas K.
The price is ￥22,611
￥39,185 total
includes taxes & fees
Nov 16 - Nov 17
Charming Celtic Cottage Retreat – 2 Bed, 1 Bath Haven"
A wooden deck with a table and chairs, a white building with large windows, and a wooden fence.

7. 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 ￥32,387
￥37,214 total
includes taxes & fees
Nov 11 - Nov 12
Beautiful Historic Cottage, Nantucket
A covered porch with white wicker furniture and green cushions, large windows, and a ceiling fan.

8. 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 ￥40,525
￥46,405 total
includes taxes & fees
Nov 11 - Nov 12
Beautiful Historic Cottage, The Garden
A room with a television on a wooden cabinet, a table, and two chairs. There is a sofa and a window with curtains.

9. Vacation Village Resort a "Hilltop Haven" Cozy 2-bedroom cottage in Clermont

Vacation Village Resort a "Hilltop Haven" Cozy 2-bedroom cottage in Clermont
Vacation Village
10.0 out of 10, Exceptional, (1 review)
"I loved the home: the views, the sunsets, the lake, the pool, the peace and tranquility, and so much more. Clermont is truly the "Gem of the Hills". And the nearby shops: Publix, Keyfood, the small Brazilian market, Shantee's Caribbean market, etc.; there is such a variety of foods. And Salt Shack overlooking Lake Minneola is another gem. I will be coming again and again to this home and this location."
United States
Anonymous traveler
The price is ￥12,799
￥32,204 total
includes taxes & fees
Nov 18 - Nov 19
Vacation Village Resort a "Hilltop Haven" Cozy 2-bedroom cottage in Clermont
A yellow house with a porch, a black door, and a number '140' on the wall.

10. The Ingram * 3 min walk to Downtown Mt. Dora!!

The Ingram * 3 min walk to Downtown Mt. Dora!!
Mt Dora
9.8 out of 10, Exceptional, (53 reviews)
"Perfect spot. House was decorated beautifully. Loved our stay!"
United States
Mark M.
The price is ￥42,189
￥68,793 total
includes taxes & fees
Nov 14 - Nov 15
The Ingram * 3 min walk to Downtown Mt. Dora!!
A hammock tied between two wooden posts, a wooden deck, and a view of a lake with trees and a clear sky.

11. Cozy Lake Front Cottage

Cozy Lake Front Cottage
Clermont
10.0 out of 10, Exceptional, (27 reviews)
"Very nice cottage, beautiful view"
United States
rachel c.
The price is ￥23,534
￥46,726 total
includes taxes & fees
Nov 11 - Nov 12
Cozy Lake Front Cottage
A single-story house with a garage, a well-maintained lawn, and a street lamp.

12. Complimentary Golf Cart! Home in The Villages

Complimentary Golf Cart! Home in The Villages
3.0 star property
Lynnhaven
10.0 out of 10, Exceptional, (1 review)
"Awesome place and conveniently located in the villages. Hosts were kind, helpful in making the trip perfect! We will be back!"
United States
Tory
The price is ￥15,848
￥53,259 total
includes taxes & fees
Dec 1 - Dec 2
Complimentary Golf Cart! Home in The Villages
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, (18 reviews)
"This property is the perfect location for walking downtown shops and dining! "
United States
Julie
The price is ￥32,387
￥37,214 total
includes taxes & fees
Nov 11 - Nov 12
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 ￥31,444
￥78,866 total
includes taxes & fees
Nov 11 - Nov 12
Fire Pit & Yard: Updated Winter Garden Home!
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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Leesburg and related destinations

Explore the Chain of Lakes by kayak, where rangers can point you to quiet coves with the best bird watching. Downtown's historic district offers local restaurants with live music, plus antique shops where owners share stories about their treasures.

See all hotels in Leesburg
A street with a yellow building, palm trees, and parked cars.
Photo by David Cate
Open Photo by David Cate

Top reviews in Leesburg

A covered outdoor area with a pool, palm trees, and a tiled floor.
The Villages 2BR Vacation Home, Lanai & Golf Cart

The Villages 2BR Vacation Home, Lanai & Golf Cart

The Villages 2BR Vacation Home, Lanai & Golf Cart
Belvedere

10/10 Excellent

Cleanliness User friendly
United States
Kathleen
Reviewed May 2, 2026
The Villages 2BR Vacation Home, Lanai & Golf Cart

Frequently Asked Questions

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What is there to do in Leesburg near my cottage?

Once you've unpacked your bags, get out and discover the fun things Leesburg has on offer. ViaPort Florida is a great attraction to add to your to-do list.