A calm lake with autumn foliage, a dock, and houses along the shore.

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Winchester cottages

A modern house with a wooden deck and a covered outdoor area.

1. Tiny Home w/ RV Hookups

Tiny Home w/ RV Hookups
Winchester
9.0 out of 10, Wonderful, (11 reviews)
"Great place to stay! "
United States
Erica P.
$173 nightly
The price is $198
Oct 19 - Oct 20
Total with taxes and fees
Tiny Home w/ RV Hookups
A single-story house with a front porch, a garage, and a small front yard.

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

Lakes, Whiskey & More! Charming Home in Tullahoma
3.0 star property
Tullahoma
$310 nightly
The price is $363
Oct 15 - Oct 16
Total with taxes and fees
Lakes, Whiskey & More! Charming Home in Tullahoma
A wooden deck with a metal table and chairs, overlooking a fenced yard with trees and a distant building.

3. Story-time Stay at Our Rupert Cottage!

Story-time Stay at Our Rupert Cottage!
Monteagle
8.8 out of 10, Excellent, (6 reviews)
"Pet friendly, host communication was excellent. The cottage was tidy and clean. "
United States
Taroub F.
$220 nightly
The price is $235
Oct 15 - Oct 16
Total with taxes and fees
Story-time Stay at Our Rupert Cottage!
A covered porch with a table and chairs, a potted plant, and a view of the surrounding trees.

4. Cozy Cottage in Monteagle!

Cozy Cottage in Monteagle!
Monteagle
9.0 out of 10, Wonderful, (2 reviews)
"Very nice cabin. It was convenient to our activities and had everything that we needed."
United States
Rebecca
$218 nightly
The price is $218
Oct 18 - Oct 19
Total with taxes and fees
Cozy Cottage in Monteagle!
A wooden cabin with a deck and a small porch, surrounded by trees.

5. Snuggle Up in our Teddy Cottage! *New Listing*

Snuggle Up in our Teddy Cottage! *New Listing*
Monteagle
10.0 out of 10, Exceptional, (8 reviews)
"I really enjoyed my stay here with my girlfriend and our two dogs. The cottage & surrounding area is super cute and cozy. There is also a nice walking trail right outside the entrance of the lodging area that we got to use. This is for sure a place I would stay at again!"
United States
Samantha B.
$213 nightly
The price is $213
Oct 15 - Oct 16
Total with taxes and fees
Snuggle Up in our Teddy Cottage! *New Listing*
A modern building with a unique facade featuring large windows and a flat roof.

6. Catch Some ZZZ's at the Grizzly Cottage

Catch Some ZZZ's at the Grizzly Cottage
Monteagle
9.8 out of 10, Exceptional, (12 reviews)
"Very comfortable and clean, close to hiking trails. We enjoyed our stay very much!"
United States
Marni F.
$256 nightly
The price is $277
Oct 15 - Oct 16
Total with taxes and fees
Catch Some ZZZ's at the Grizzly Cottage
A modern building with a unique facade featuring large windows and a flat roof.

7. Smarter than the Average Stay at the Yogi Cottage!

Smarter than the Average Stay at the Yogi Cottage!
Monteagle
9.2 out of 10, Wonderful, (10 reviews)
"We had the best time. The place was really nice. We loved the bear statues that decorated the establishment. Communication was good. Interior was visually appealing."
United States
Shanna R.
$220 nightly
The price is $220
Oct 15 - Oct 16
Total with taxes and fees
Smarter than the Average Stay at the Yogi Cottage!
A white house with a red roof and a porch, surrounded by trees and grass.

8. Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast

Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast
Mulberry
10.0 out of 10, Exceptional, (44 reviews)
"Beautiful property and wonderful proprietors."
United States
Dawn K.
$294 nightly
The price is $332
Oct 17 - Oct 18
Total with taxes and fees
Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast
Exterior

9. Country Rose Cottage

Country Rose Cottage
Tracy City
10.0 out of 10, Exceptional, (2 reviews)
"We loved the cute cottage. So cozy and so convenient!!!!! We will be back !!!"
United States
Melinda S.
$185 nightly
The price is $216
Oct 15 - Oct 16
Total with taxes and fees
Country Rose Cottage
A modern building with a unique facade featuring large windows and a flat roof.

10. Visit 100 Aker Woods and Stay at Winnie Cottage!

Visit 100 Aker Woods and Stay at Winnie Cottage!
Monteagle
10.0 out of 10, Exceptional, (14 reviews)
"This place was awesome! Super clean, with everything I needed. Very peaceful"
United States
Christina H.
$220 nightly
The price is $220
Oct 15 - Oct 16
Total with taxes and fees
Visit 100 Aker Woods and Stay at Winnie Cottage!
A small, single-story house with a porch and a fenced yard.

11. Have the Sweetest Dreams @ the Honey Bear Cottage!

Have the Sweetest Dreams @ the Honey Bear Cottage!
Monteagle
10.0 out of 10, Exceptional, (5 reviews)
"Very easy to book and to navigate. "
United States
Lynn A.
$218 nightly
The price is $218
Nov 8 - Nov 9
Total with taxes and fees
Have the Sweetest Dreams @ the Honey Bear Cottage!
A single-story house with a front porch, a staircase leading to the entrance, and a small patio area.

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

Tullahoma Whiskey Trail Base w/ Yard & Fire Pit
3.0 star property
Tullahoma
$438 nightly
The price is $513
Oct 15 - Oct 16
Total with taxes and fees
Tullahoma Whiskey Trail Base w/ Yard & Fire Pit
A covered porch with a wooden bench and a cushioned seating area, surrounded by trees.

13. Picturesque Tiny Cottage with Cozy Indoor and Outdoor in Tennessee

Picturesque Tiny Cottage with Cozy Indoor and Outdoor in Tennessee
Monteagle
10.0 out of 10, Exceptional, (1 review)
"Everything worked and functional as advertised. Property is at end of road and quiet with no one driving by"
United States
Francis P.
$287 nightly
The price is $334
Oct 21 - Oct 22
Total with taxes and fees
Picturesque Tiny Cottage with Cozy Indoor and Outdoor in Tennessee
A two-story house with a covered porch, surrounded by a well-maintained lawn and trees.

14. Peaceful Mountaintop Cottage

Peaceful Mountaintop Cottage
Tracy City
9.8 out of 10, Exceptional, (20 reviews)
"Great location, spacious entertainment areas!"
United States
Karen F.
$364 nightly
The price is $426
Oct 15 - Oct 16
Total with taxes and fees
Peaceful Mountaintop Cottage
A modern building with a unique facade featuring large windows and a flat roof.

15. Only You Can Stay at the Smokey the Bear Cottage!

Only You Can Stay at the Smokey the Bear Cottage!
Monteagle
$215 nightly
The price is $215
Oct 15 - Oct 16
Total with taxes and fees
Only You Can Stay at the Smokey the Bear Cottage!
A modern cabin with a stone foundation, large windows, and a view of the surrounding forest.

16. Outstanding Cottage with Stunning Sights in Monteagle, Tennessee

Outstanding Cottage with Stunning Sights in Monteagle, Tennessee
Monteagle
$297 nightly
The price is $346
Oct 18 - Oct 19
Total with taxes and fees
Outstanding Cottage with Stunning Sights in Monteagle, Tennessee
A covered outdoor patio with a round table and chairs, a ceiling fan, and a view of a grassy field.

17. Adorable 1 bedroom tiny home w/ loft situated on 156 acres in Shelbyville, TN

Adorable 1 bedroom tiny home w/ loft situated on 156 acres in Shelbyville, TN
Shelbyville
10.0 out of 10, Exceptional, (16 reviews)
"Excellent place super comfortable, cozy and beautiful. It has all you need and the details of the hosts are amazing."
United States
rafael z.
$178 nightly
The price is $204
Oct 15 - Oct 16
Total with taxes and fees
Adorable 1 bedroom tiny home w/ loft situated on 156 acres in Shelbyville, TN
A brick pathway leading to a white building with a metal roof, surrounded by a white picket fence and various plants.

18. Hilltop Cottage • Peaceful Escape Near Nashville • Perfect for Couples & Pets

Hilltop Cottage • Peaceful Escape Near Nashville • Perfect for Couples & Pets
Shelbyville
8.0 out of 10, Very good, (4 reviews)
"Great location, great host."
United States
Jerry H.
$154 nightly
The price is $176
Oct 15 - Oct 16
Total with taxes and fees
Hilltop Cottage • Peaceful Escape Near Nashville • Perfect for Couples & Pets
A two-story house with a covered patio area, a deck, and a view of a lake.

19. Swordfish Suite DOG friendly- Pup Shed Retreat

Swordfish Suite DOG friendly- Pup Shed Retreat
Tracy City
10.0 out of 10, Exceptional, (19 reviews)
"Enjoyed our stay."
United States
Mark P.
$323 nightly
The price is $378
Nov 2 - Nov 3
Total with taxes and fees
Swordfish Suite DOG friendly- Pup Shed Retreat
A wooden deck with a railing, two stools, and a bench overlooking a forest.

20. Stunning Cottage Nestled Amidst Trees with Fire Pit in Monteagle, Tennessee

Stunning Cottage Nestled Amidst Trees with Fire Pit in Monteagle, Tennessee
Monteagle
$290 nightly
The price is $338
Nov 1 - Nov 2
Total with taxes and fees
Stunning Cottage Nestled Amidst Trees with Fire Pit in Monteagle, Tennessee
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 Winchester Hotel Reviews

The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

8/10 Good
"Handy access........................."
Gregory 1-night trip
Posted 1 day ago
The Smokehouse Lodge and Cabins

Find out more about Winchester

Winchester Cottages information

Number of reviews
135
Accommodation
77 Cottages
Lowest Price
$176
Highest Price
$513

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.

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