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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

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.
The price is SAR 405
SAR 816 total
includes taxes & fees
9 Nov - 10 Nov
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
The price is SAR 473
SAR 1,362 total
includes taxes & fees
13 Oct - 14 Oct
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.
The price is SAR 301
SAR 875 total
includes taxes & fees
9 Nov - 10 Nov
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
The price is SAR 301
SAR 825 total
includes taxes & fees
21 Oct - 22 Oct
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.
The price is SAR 281
SAR 793 total
includes taxes & fees
9 Nov - 10 Nov
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.
The price is SAR 382
SAR 1,035 total
includes taxes & fees
23 Oct - 24 Oct
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.
The price is SAR 301
SAR 817 total
includes taxes & fees
15 Oct - 16 Oct
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.
The price is SAR 788
SAR 1,245 total
includes taxes & fees
11 Oct - 12 Oct
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, (1 review)
"We loved the cute cottage. So cozy and so convenient!!!!! We will be back !!!"
United States
Melinda S.
The price is SAR 443
SAR 812 total
includes taxes & fees
23 Oct - 24 Oct
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.
The price is SAR 301
SAR 817 total
includes taxes & fees
14 Oct - 15 Oct
Visit 100 Aker Woods and Stay at Winnie Cottage!
A two-story house with a covered porch, surrounded by a well-maintained lawn and trees.

11. Peaceful Mountaintop Cottage

Peaceful Mountaintop Cottage
Tracy City
9.8 out of 10, Exceptional, (19 reviews)
"Great location, spacious entertainment areas!"
United States
Karen F.
The price is SAR 845
SAR 1,590 total
includes taxes & fees
23 Oct - 24 Oct
Peaceful Mountaintop 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
The price is SAR 725
SAR 1,927 total
includes taxes & fees
19 Oct - 20 Oct
Tullahoma Whiskey Trail Base w/ Yard & Fire Pit
A modern building with a unique facade featuring large windows and a flat roof.

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

Only You Can Stay at the Smokey the Bear Cottage!
Monteagle
The price is SAR 301
SAR 806 total
includes taxes & fees
21 Oct - 22 Oct
Only You Can Stay at the Smokey the Bear Cottage!
A small, single-story house with a porch and a fenced yard.

14. 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.
Have the Sweetest Dreams @ the Honey Bear Cottage!
A covered outdoor patio with a round table and chairs, a ceiling fan, and a view of a grassy field.

15. 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, (15 reviews)
The price is SAR 469
SAR 740 total
includes taxes & fees
11 Oct - 12 Oct
Adorable 1 bedroom tiny home w/ loft situated on 156 acres in Shelbyville, TN
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.
The price is SAR 946
SAR 1,254 total
includes taxes & fees
2 Nov - 3 Nov
Picturesque Tiny Cottage with Cozy Indoor and Outdoor in Tennessee
A two-story house with a covered patio area, a deck, and a view of a lake.

17. Swordfish Suite DOG friendly- Pup Shed Retreat

Swordfish Suite DOG friendly- Pup Shed Retreat
Tracy City
10.0 out of 10, Exceptional, (19 reviews)
Swordfish Suite DOG friendly- Pup Shed Retreat
A wooden deck with a sofa and chairs, overlooking a forest.

18. Outstanding Cottage with Stunning Sights in Monteagle, Tennessee

Outstanding Cottage with Stunning Sights in Monteagle, Tennessee
Monteagle
The price is SAR 984
SAR 1,311 total
includes taxes & fees
3 Nov - 4 Nov
Outstanding Cottage with Stunning Sights in Monteagle, Tennessee
A cabin with a gravel driveway, surrounded by dense forest.

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

Stunning Cottage Nestled Amidst Trees with Fire Pit in Monteagle, Tennessee
Monteagle
The price is SAR 997
SAR 1,312 total
includes taxes & fees
28 Oct - 29 Oct
Stunning Cottage Nestled Amidst Trees with Fire Pit in Monteagle, Tennessee
A brick pathway leading to a white building with a metal roof, surrounded by a white picket fence and various plants.

20. 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.
The price is SAR 352
SAR 661 total
includes taxes & fees
12 Oct - 13 Oct
Hilltop Cottage • Peaceful Escape Near Nashville • Perfect for Couples & Pets
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
"Very clean, breakfast was very good and clean, good variety of breakfast food, the lady kept the breakfast area immaculate, room was nice and huge shower. Only complaint was it was a little noisy in the room above us or beside us, not sure if walls were thin. Also on my husbands side of bed light did not work or could of just needed a bulb, we did not report, but overall very nice place"
Martin 3-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

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