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

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Our top choices for Winchester cottages

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 AU$284
includes taxes & fees
16 Nov - 17 Nov
Tiny Home w/ RV Hookups

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

Lakes, Whiskey & More! Charming Home in Tullahoma
3.0 star property
Tullahoma
The price is AU$549
includes taxes & fees
16 Nov - 17 Nov
Lakes, Whiskey & More! Charming Home in Tullahoma

3. 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, (11 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 AU$318
includes taxes & fees
9 Nov - 10 Nov
Smarter than the Average Stay at the Yogi Cottage!

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 AU$302
includes taxes & fees
19 Nov - 20 Nov
Cozy Cottage in Monteagle!

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 AU$309
includes taxes & fees
30 Nov - 1 Dec
Snuggle Up in our Teddy Cottage! *New Listing*

6. Catch Some ZZZ's at the Grizzly Cottage

Catch Some ZZZ's at the Grizzly Cottage
Monteagle
9.8 out of 10, Exceptional, (13 reviews)
"We were very pleased with everything about this rental. Check-in and out were smooth, the host was very responsive and helpful when we had a question. We plan to stay again whenever we’re in the area!"
United States
Stephen C.
The price is AU$399
includes taxes & fees
9 Nov - 10 Nov
Catch Some ZZZ's at the Grizzly Cottage

7. 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 AU$318
includes taxes & fees
9 Nov - 10 Nov
Have the Sweetest Dreams @ the Honey Bear Cottage!

8. 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 AU$318
includes taxes & fees
9 Nov - 10 Nov
Visit 100 Aker Woods and Stay at Winnie Cottage!

9. Country Rose Cottage

Country Rose Cottage
Tracy City
10.0 out of 10, Exceptional, (3 reviews)
"We loved the cute cottage. So cozy and so convenient!!!!! We will be back !!!"
United States
Melinda S.
The price is AU$304
includes taxes & fees
9 Nov - 10 Nov
Country Rose Cottage

10. 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 AU$458
includes taxes & fees
13 Nov - 14 Nov
Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast

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

Only You Can Stay at the Smokey the Bear Cottage!
Monteagle
The price is AU$310
includes taxes & fees
9 Nov - 10 Nov
Only You Can Stay at the Smokey the Bear Cottage!

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 AU$747
includes taxes & fees
9 Nov - 10 Nov
Tullahoma Whiskey Trail Base w/ Yard & Fire Pit

13. 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 AU$589
includes taxes & fees
18 Nov - 19 Nov
Peaceful Mountaintop Cottage

14. 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 AU$527
includes taxes & fees
9 Nov - 10 Nov
Swordfish Suite DOG friendly- Pup Shed Retreat

15. 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 AU$503
includes taxes & fees
19 Nov - 20 Nov
Stunning Cottage Nestled Amidst Trees with Fire Pit in Monteagle, Tennessee

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

Hilltop Cottage • Peaceful Escape Near Nashville • Perfect for Couples & Pets
Shelbyville
8.4 out of 10, Very good, (6 reviews)
"Property was wonderful and very cozy. Perfect little getaway from everyday life. "
United States
Kathy P.
The price is AU$247
includes taxes & fees
9 Nov - 10 Nov
Hilltop Cottage • Peaceful Escape Near Nashville • Perfect for Couples & Pets

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, (18 reviews)
"We had a great 3 night stay. Will definitely stay here again when in the area."
United States
Jeff S.
The price is AU$284
includes taxes & fees
9 Nov - 10 Nov
Adorable 1 bedroom tiny home w/ loft situated on 156 acres in Shelbyville, TN

18. Outstanding Cottage with Stunning Sights in Monteagle, Tennessee

Outstanding Cottage with Stunning Sights in Monteagle, Tennessee
Monteagle
The price is AU$496
includes taxes & fees
8 Dec - 9 Dec
Outstanding Cottage with Stunning Sights in Monteagle, Tennessee

19. Magical Tiny Cottage with Lovely Outdoor Living in Tennessee

Magical Tiny Cottage with Lovely Outdoor Living in Tennessee
Tracy City
The price is AU$560
includes taxes & fees
19 Nov - 20 Nov
Magical Tiny Cottage with Lovely Outdoor Living in Tennessee

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

Breathtaking Cottage with Fire Pit in Tracy City, Tennessee
Tracy City
The price is AU$557
includes taxes & fees
9 Nov - 10 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

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Winchester Cottages information

Number of reviews
115
Accommodation
76 Cottages
Lowest Price
AU$247
Highest Price
AU$747

Frequently asked questions

What is there to do in Winchester near my cottage?
The ideal travel accessory is a well-planned schedule. Tims Ford State Park is a wonderful place to kick-start your exploration of Winchester.