Search Cottages in Winchester

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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Winchester cottages

A single-story house with a front porch, a garage, and a small front yard.

1. Lakes, Whiskey & More! Charming Home in Tullahoma

Lakes, Whiskey & More! Charming Home in Tullahoma
3.0 star property
Tullahoma
The price is RM559
RM1,526 total
includes taxes & fees
15 Nov - 16 Nov
Lakes, Whiskey & More! Charming Home in Tullahoma
A single-story house with a front porch, a staircase leading to the entrance, and a small patio area.

2. Tullahoma Whiskey Trail Base w/ Yard & Fire Pit

Tullahoma Whiskey Trail Base w/ Yard & Fire Pit
3.0 star property
Tullahoma
The price is RM782
RM2,078 total
includes taxes & fees
9 Nov - 10 Nov
Tullahoma Whiskey Trail Base w/ Yard & Fire Pit
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 Winchester

Nestled between rolling hills, this charming town offers visitors the crystal-clear waters of Tims Ford Lake for boating and fishing. Explore downtown's historic courthouse square where local shops serve up Southern hospitality alongside the famous Winchester Swamp Festival each September.

See all hotels in Winchester
A calm lake with autumn foliage, a dock, and houses along the shore.

Frequently Asked Questions

Why book your cottage in Winchester with Expedia?

Expedia has some excellent cottages in Winchester, so start packing for an unforgettable stay on nature's doorstep. If you have a fixed budget, select how much you're willing to spend and the preferred star rating of your property. Or, use our filters to search for cottages with a kitchen or a pool. We'll help you find the right place whatever your bank balance or plans.

How can I find cheap cottages in Winchester?

An excellent way to find cheap cottages in Winchester is with Expedia's user-friendly filter tool. Narrow your search by budget, star rating and amenities to take advantage of unbeatable rates in just a few keystrokes.

What is there to do in Winchester near my cottage?

The most useful travel accessory is a well-planned itinerary. Tim's Ford Marina is a terrific place to start your exploration of Winchester.