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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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.
$165 nightly
The price is $189
Nov 16 - Nov 17
Total with taxes and fees
Tiny Home w/ RV Hookups
A modern building with a unique facade featuring large windows and a flat roof.

2. 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.
$216 nightly
The price is $216
Nov 13 - Nov 14
Total with taxes and fees
Smarter than the Average Stay at the Yogi Cottage!
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
Nov 15 - Nov 16
Total with taxes and fees
Lakes, Whiskey & More! Charming Home in Tullahoma
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
$217 nightly
The price is $217
Nov 19 - Nov 20
Total with taxes and fees
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.
$210 nightly
The price is $210
Nov 30 - Dec 1
Total with taxes and fees
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, (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.
$252 nightly
The price is $273
Nov 15 - Nov 16
Total with taxes and fees
Catch Some ZZZ's at the Grizzly Cottage
Exterior

7. Country Rose Cottage

Country Rose Cottage
Tracy City
10.0 out of 10, Exceptional, (4 reviews)
"We loved the cute cottage. So cozy and so convenient!!!!! We will be back !!!"
United States
Melinda S.
$175 nightly
The price is $206
Nov 13 - Nov 14
Total with taxes and fees
Country Rose Cottage
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.
$216 nightly
The price is $216
Nov 15 - Nov 16
Total with taxes and fees
Have the Sweetest Dreams @ the Honey Bear Cottage!
A two-story house with a dark shingle roof, a front porch with steps, and a front door with a wreath.

9. Cascade Hollow Cottage Next to Dickel Distillery

Cascade Hollow Cottage Next to Dickel Distillery
Normandy
8.0 out of 10, Very good, (1 review)
"Such a cute place with a beautiful setting."
United States
Angela S.
$270 nightly
The price is $313
Nov 13 - Nov 14
Total with taxes and fees
Cascade Hollow Cottage Next to Dickel Distillery
A white house with a red roof and a porch, surrounded by trees and grass.

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.
$280 nightly
The price is $318
Nov 13 - Nov 14
Total with taxes and fees
Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast
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
8.4 out of 10, Very good, (6 reviews)
"Property was wonderful and very cozy. Perfect little getaway from everyday life. "
United States
Kathy P.
$146 nightly
The price is $168
Nov 13 - Nov 14
Total with taxes and fees
Hilltop Cottage • Peaceful Escape Near Nashville • Perfect for Couples & Pets
A two-story house with a covered patio area, a deck, and a view of a lake.

12. 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.
$310 nightly
The price is $365
Nov 17 - Nov 18
Total with taxes and fees
Swordfish Suite DOG friendly- Pup Shed Retreat
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
Nov 13 - Nov 14
Total with taxes and fees
Tullahoma Whiskey Trail Base w/ Yard & Fire Pit
A modern building with a unique facade featuring large windows and a flat roof.

14. 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.
$216 nightly
The price is $216
Nov 15 - Nov 16
Total with taxes and fees
Visit 100 Aker Woods and Stay at Winnie 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, (18 reviews)
"We had a great 3 night stay. Will definitely stay here again when in the area."
United States
Jeff S.
$169 nightly
The price is $195
Nov 13 - Nov 14
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 porch, surrounded by a well-maintained lawn and trees.

16. 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.
$345 nightly
The price is $407
Nov 15 - Nov 16
Total with taxes and fees
Peaceful Mountaintop Cottage
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
$212 nightly
The price is $212
Nov 15 - Nov 16
Total with taxes and fees
Only You Can Stay at the Smokey the Bear Cottage!
A cabin with a wooden deck and a staircase leading to the entrance.

18. 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.
$317 nightly
The price is $353
Nov 16 - Nov 17
Total with taxes and fees
Stunning Cottage Nestled Amidst Trees with Fire Pit in Monteagle, Tennessee
A cabin with a wooden deck, surrounded by trees and rocks.

19. Outstanding Cottage with Stunning Sights in Monteagle, Tennessee

Outstanding Cottage with Stunning Sights in Monteagle, Tennessee
Monteagle
$313 nightly
The price is $348
Nov 16 - Nov 17
Total with taxes and fees
Outstanding Cottage with Stunning Sights in Monteagle, Tennessee
A two-story cabin with a covered porch and a staircase leading to the entrance.

20. Fantastic Cozy Cottage Nestled Amidst Trees in Tracy City, Tennessee

Fantastic Cozy Cottage Nestled Amidst Trees in Tracy City, Tennessee
Tracy City
10.0 out of 10, Exceptional, (1 review)
"This was by far the best VRBO I have stayed at that was as advertised! The previous VRBO I rented looked good in pictures but was not as advertised.Besides this being a great rental, it was an awesome and amazing community. Will definitely plan on coming back here again.."
United States
Tim B.
$376 nightly
The price is $436
Nov 14 - Nov 15
Total with taxes and fees
Fantastic Cozy Cottage Nestled Amidst Trees 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

La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

10/10 Excellent
"Very helpful front desk. Description stated sleeps 3 but extra"
Steve 1-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

Find out more about Winchester

Winchester Cottages information

Number of reviews
121
Accommodation
77 Cottages
Lowest Price
$168
Highest Price
$513

Frequently asked questions

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Expedia has some excellent cottages in Winchester, so start packing for an unforgettable stay on nature's doorstep. If you have a fixed budget, select how much you're willing to spend and the preferred star rating of your property. Or, use our filters to search for cottages with a kitchen or a pool. We'll help you find the right place whatever your bank balance or plans.
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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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