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

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In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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.
$177 nightly
The price is $203
Oct 27 - Oct 28
Total with taxes and fees
Tiny Home w/ RV Hookups
A covered porch with a table and chairs, a potted plant, and a view of the surrounding trees.

2. 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
$220 nightly
The price is $220
Oct 26 - Oct 27
Total with taxes and fees
Cozy Cottage in Monteagle!
A single-story house with a front porch, a garage, and a small front yard.

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

Lakes, Whiskey & More! Charming Home in Tullahoma
3.0 star property
Tullahoma
$322 nightly
The price is $377
Oct 26 - Oct 27
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.

4. 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 26 - Oct 27
Total with taxes and fees
Story-time Stay at Our Rupert Cottage!
A modern building with a unique facade featuring large windows and a flat roof.

5. 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 26 - Oct 27
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.

6. 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 26 - Oct 27
Total with taxes and fees
Smarter than the Average Stay at the Yogi Cottage!
Exterior

7. 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.
$184 nightly
The price is $215
Oct 31 - Nov 1
Total with taxes and fees
Country Rose 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.
$295 nightly
The price is $333
Oct 26 - Oct 27
Total with taxes and fees
Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast
A modern building with a unique facade featuring large windows and a flat roof.

9. 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 26 - Oct 27
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.

10. 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.
$220 nightly
The price is $220
Nov 8 - Nov 9
Total with taxes and fees
Have the Sweetest Dreams @ the Honey Bear Cottage!
A brick pathway leading to a white building with a metal roof, surrounded by a white picket fence and various plants.

11. 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 26 - Oct 27
Total with taxes and fees
Hilltop Cottage • Peaceful Escape Near Nashville • Perfect for Couples & Pets
A two-story house with a covered porch, surrounded by a well-maintained lawn and trees.

12. 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 26 - Oct 27
Total with taxes and fees
Peaceful Mountaintop Cottage
A single-story house with a front porch, a staircase leading to the entrance, and a small patio area.

13. 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 28 - Oct 29
Total with taxes and fees
Tullahoma Whiskey Trail Base w/ Yard & Fire Pit
A covered outdoor patio with a round table and chairs, a ceiling fan, and a view of a grassy field.

14. 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, (17 reviews)
"We had a great 3 night stay. Will definitely stay here again when in the area."
United States
Jeff S.
$178 nightly
The price is $204
Oct 26 - Oct 27
Total with taxes and fees
Adorable 1 bedroom tiny home w/ loft situated on 156 acres in Shelbyville, TN
A two-story house with a covered patio area, a deck, and a view of a lake.

15. 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.
$318 nightly
The price is $372
Oct 26 - Oct 27
Total with taxes and fees
Swordfish Suite DOG friendly- Pup Shed Retreat
A cabin with a deck, surrounded by a forest.

16. 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 26 - Oct 27
Total with taxes and fees
Picturesque Tiny Cottage with Cozy Indoor and Outdoor in Tennessee
A cabin with a wooden deck, surrounded by trees and rocks.

17. Outstanding Cottage with Stunning Sights in Monteagle, Tennessee

Outstanding Cottage with Stunning Sights in Monteagle, Tennessee
Monteagle
$288 nightly
The price is $335
Oct 26 - Oct 27
Total with taxes and fees
Outstanding Cottage with Stunning Sights in Monteagle, Tennessee
A two-story house with a porch, a fenced yard, and a gravel driveway.

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

Only You Can Stay at the Smokey the Bear Cottage!
Monteagle
$214 nightly
The price is $214
Oct 26 - Oct 27
Total with taxes and fees
Only You Can Stay at the Smokey the Bear Cottage!
A cabin with a gravel driveway and a wooden fence.

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

Stunning Cottage Nestled Amidst Trees with Fire Pit in Monteagle, Tennessee
Monteagle
$292 nightly
The price is $340
Oct 27 - Oct 28
Total with taxes and fees
Stunning Cottage Nestled Amidst Trees with Fire Pit in Monteagle, Tennessee
A stone cabin with a sloped roof, large windows, and a stone exterior.

20. Magical Tiny Cottage with Lovely Outdoor Living in Tennessee

Magical Tiny Cottage with Lovely Outdoor Living in Tennessee
Tracy City
$301 nightly
The price is $368
Oct 27 - Oct 28
Total with taxes and fees
Magical Tiny Cottage with Lovely Outdoor Living in 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

La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

8/10 Good
"Property was clean, conveniently located, staff was good. However, I had no hot water in the sink faucet. I told the staff the day after arrived/checked in (Monday). They said someone will take care of it the next day as it was evening when I told them. It wasn't fixed during my stay - I left on Friday. The shower had the hot water."
Muhammad 5-night trip
Posted 4 hours ago
La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

Find out more about Winchester

Winchester Cottages information

Number of reviews
119
Accommodation
77 Cottages
Lowest Price
$176
Highest Price
$513

Frequently asked questions

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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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