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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 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 €185
includes taxes & fees
2 Nov - 3 Nov
Tiny Home w/ RV Hookups
A log cabin with a deck, large windows, and a patio area.

2. Story-time Stay at Our Rupert Cottage!

Story-time Stay at Our Rupert Cottage!
Monteagle
9.0 out of 10, Wonderful, (7 reviews)
"Pet friendly, host communication was excellent. The cottage was tidy and clean. "
United States
Taroub F.
The price is €230
includes taxes & fees
30 Oct - 31 Oct
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.

3. 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 €199
includes taxes & fees
29 Nov - 30 Nov
Cozy Cottage in Monteagle!
A modern building with a unique facade featuring large windows and a flat roof.

4. 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 €254
includes taxes & fees
30 Oct - 31 Oct
Catch Some ZZZ's at the Grizzly Cottage
A single-story house with a front porch, a garage, and a small front yard.

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

Lakes, Whiskey & More! Charming Home in Tullahoma
3.0 star property
Tullahoma
The price is €338
includes taxes & fees
12 Nov - 13 Nov
Lakes, Whiskey & More! Charming Home in Tullahoma
A wooden cabin with a front porch, a small front door, and a window.

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 €199
includes taxes & fees
29 Nov - 30 Nov
Smarter than the Average Stay at the Yogi Cottage!
A white house with a red roof and a porch, surrounded by trees and grass.

7. 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 €303
includes taxes & fees
12 Nov - 13 Nov
Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast
A small, single-story house with a porch and a fenced yard.

8. 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 €201
includes taxes & fees
8 Nov - 9 Nov
Have the Sweetest Dreams @ the Honey Bear Cottage!
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.
The price is €199
includes taxes & fees
2 Nov - 3 Nov
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 €203
includes taxes & fees
1 Nov - 2 Nov
Visit 100 Aker Woods and Stay at Winnie 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 €162
includes taxes & fees
3 Nov - 4 Nov
Hilltop Cottage • Peaceful Escape Near Nashville • Perfect for Couples & Pets
A covered outdoor patio with a round table and chairs, a ceiling fan, and a view of a grassy field.

12. 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 €184
includes taxes & fees
12 Nov - 13 Nov
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.

13. 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 €340
includes taxes & fees
1 Nov - 2 Nov
Swordfish Suite DOG friendly- Pup Shed Retreat
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
10.0 out of 10, Exceptional, (21 reviews)
"Great location, spacious entertainment areas!"
United States
Karen F.
The price is €369
includes taxes & fees
1 Nov - 2 Nov
Peaceful Mountaintop Cottage
A single-story house with a front porch, a staircase leading to the entrance, and a small patio area.

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

Tullahoma Whiskey Trail Base w/ Yard & Fire Pit
3.0 star property
Tullahoma
The price is €460
includes taxes & fees
12 Nov - 13 Nov
Tullahoma Whiskey Trail Base w/ Yard & Fire Pit
A cabin with a gravel driveway and a wooden fence.

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

Stunning Cottage Nestled Amidst Trees with Fire Pit in Monteagle, Tennessee
Monteagle
10.0 out of 10, Exceptional, (1 review)
"This place was just perfect! It was close to some lovely hiking and had a private view of the creek. The back yard with the fire pit was nice with lots of kindling available. The cabin seemed to have everything you could want. It was cozy, and we enjoyed cooking on the stove, in the oven, and on the grill. The location was central to all the good hiking, too. I hope to return!"
United States
Tracy M.
The price is €302
includes taxes & fees
2 Nov - 3 Nov
Stunning Cottage Nestled Amidst Trees with Fire Pit in Monteagle, Tennessee
A two-story house with a porch, a fenced yard, and a gravel driveway.

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

Only You Can Stay at the Smokey the Bear Cottage!
Monteagle
The price is €195
includes taxes & fees
1 Nov - 2 Nov
Only You Can Stay at the Smokey the Bear Cottage!
A cabin with a wooden deck, surrounded by trees and rocks.

18. Outstanding Cottage with Stunning Sights in Monteagle, Tennessee

Outstanding Cottage with Stunning Sights in Monteagle, Tennessee
Monteagle
The price is €311
includes taxes & fees
2 Nov - 3 Nov
Outstanding Cottage with Stunning Sights in Monteagle, Tennessee
A stone cabin with a sloped roof, large windows, and a stone exterior.

19. Magical Tiny Cottage with Lovely Outdoor Living in Tennessee

Magical Tiny Cottage with Lovely Outdoor Living in Tennessee
Tracy City
The price is €341
includes taxes & fees
2 Nov - 3 Nov
Magical Tiny Cottage with Lovely Outdoor Living in Tennessee
A wooden deck with outdoor seating, a barbecue grill, and a view of a lake with trees and a small building in the background.

20. Breathtaking Cottage with Fire Pit in Tracy City, Tennessee

Breathtaking Cottage with Fire Pit in Tracy City, Tennessee
Tracy City
The price is €336
includes taxes & fees
1 Nov - 2 Nov
Breathtaking Cottage with Fire Pit in Tracy City, 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

Microtel Inn & Suites by Wyndham Manchester

Microtel Inn & Suites by Wyndham Manchester

10/10 Excellent
"Off the beaten path--by a block, so convenient."
Gregory 2-night trip
Posted 2 days ago
Microtel Inn & Suites by Wyndham Manchester

Find out more about Winchester

Winchester Cottages information

Number of reviews
113
Accommodation
76 Cottages
Lowest Price
€162
Highest Price
€460

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.