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 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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.
$174 nightly
The price is $199
Nov 2 - Nov 3
Total with taxes and fees
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.
$226 nightly
The price is $242
Oct 30 - Oct 31
Total with taxes and fees
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
$218 nightly
The price is $218
Nov 1 - Nov 2
Total with taxes and fees
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.
$254 nightly
The price is $275
Oct 30 - Oct 31
Total with taxes and fees
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
$322 nightly
The price is $377
Nov 2 - Nov 3
Total with taxes and fees
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.
$218 nightly
The price is $218
Oct 30 - Oct 31
Total with taxes and fees
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.
$296 nightly
The price is $334
Oct 30 - Oct 31
Total with taxes and fees
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.
$220 nightly
The price is $220
Nov 8 - Nov 9
Total with taxes and fees
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.
$185 nightly
The price is $216
Nov 2 - Nov 3
Total with taxes and fees
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.
$218 nightly
The price is $218
Nov 1 - Nov 2
Total with taxes and fees
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.
$154 nightly
The price is $176
Oct 30 - Oct 31
Total with taxes and fees
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.
$177 nightly
The price is $203
Nov 4 - Nov 5
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 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.
$323 nightly
The price is $378
Nov 1 - Nov 2
Total with taxes and fees
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.
$361 nightly
The price is $423
Nov 1 - Nov 2
Total with taxes and fees
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
$438 nightly
The price is $513
Nov 1 - Nov 2
Total with taxes and fees
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.
$293 nightly
The price is $341
Nov 3 - Nov 4
Total with taxes and fees
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
$213 nightly
The price is $213
Nov 1 - Nov 2
Total with taxes and fees
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
$294 nightly
The price is $342
Nov 2 - Nov 3
Total with taxes and fees
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
$314 nightly
The price is $381
Oct 30 - Oct 31
Total with taxes and fees
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
$305 nightly
The price is $369
Nov 2 - Nov 3
Total with taxes and fees
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
77 Cottages
Lowest Price
$176
Highest Price
$513

Frequently asked questions

Why book your cottage in Winchester with Expedia?
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.
How can I find cheap cottages in Winchester?
An excellent way to find cheap cottages in Winchester is with Expedia's user-friendly filter tool. Narrow your search by budget, star rating and amenities to take advantage of unbeatable rates in just a few keystrokes.
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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