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

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 NZ$354
includes taxes & fees
26 Oct - 27 Oct
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
The price is NZ$377
includes taxes & fees
25 Oct - 26 Oct
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
The price is NZ$637
includes taxes & fees
25 Oct - 26 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.

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.
The price is NZ$404
includes taxes & fees
25 Oct - 26 Oct
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.
The price is NZ$482
includes taxes & fees
28 Oct - 29 Oct
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.
The price is NZ$380
includes taxes & fees
28 Oct - 29 Oct
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.
The price is NZ$374
includes taxes & fees
31 Oct - 1 Nov
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.
The price is NZ$566
includes taxes & fees
6 Nov - 7 Nov
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.
The price is NZ$380
includes taxes & fees
26 Oct - 27 Oct
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.
The price is NZ$375
includes taxes & fees
23 Nov - 24 Nov
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.
The price is NZ$309
includes taxes & fees
3 Nov - 4 Nov
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.
The price is NZ$729
includes taxes & fees
28 Oct - 29 Oct
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
The price is NZ$900
includes taxes & fees
25 Oct - 26 Oct
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.
The price is NZ$354
includes taxes & fees
25 Oct - 26 Oct
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.
The price is NZ$651
includes taxes & fees
26 Oct - 27 Oct
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.
The price is NZ$636
includes taxes & fees
5 Nov - 6 Nov
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
The price is NZ$598
includes taxes & fees
27 Oct - 28 Oct
Outstanding Cottage with Stunning Sights in Monteagle, Tennessee
A modern building with a unique facade featuring large windows and a flat roof.

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

Only You Can Stay at the Smokey the Bear Cottage!
Monteagle
The price is NZ$373
includes taxes & fees
25 Oct - 26 Oct
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
The price is NZ$596
includes taxes & fees
27 Oct - 28 Oct
Stunning Cottage Nestled Amidst Trees with Fire Pit in Monteagle, Tennessee
A deck with a sectional sofa and a round table, surrounded by wicker furniture, overlooking a forested area.

20. Magical Tiny Cottage with Lovely Outdoor Living in Tennessee

Magical Tiny Cottage with Lovely Outdoor Living in Tennessee
Tracy City
The price is NZ$644
includes taxes & fees
27 Oct - 28 Oct
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

The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

10/10 Excellent
"Had a great stay in the 1.5 bedroom cabin was perfect for the 3 of us and 2 small dogs. The front desk was super friendly and helpful when we needed our card reprogrammed. The shuttle services to the caverns was extremely convenient. Super cute property."
Dennis 2-night trip
Posted 21 hours ago
The Smokehouse Lodge and Cabins

Find out more about Winchester

Winchester Cottages information

Number of reviews
119
Accommodation
77 Cottages
Lowest Price
NZ$309
Highest Price
NZ$900

Frequently asked questions

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.