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

Search Winchester Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

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.
$165 nightly
The price is $189
Nov 16 - Nov 17
Total with taxes and fees
Tiny Home w/ RV Hookups

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 15 - Nov 16
Total with taxes and fees
Smarter than the Average Stay at the Yogi Cottage!

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
$217 nightly
The price is $217
Nov 19 - Nov 20
Total with taxes and fees
Cozy Cottage in Monteagle!

4. 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

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*

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

7. 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 15 - Nov 16
Total with taxes and fees
Cascade Hollow Cottage Next to Dickel Distillery

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!

9. 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 16 - Nov 17
Total with taxes and fees
Adorable 1 bedroom tiny home w/ loft situated on 156 acres in Shelbyville, TN

10. 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 15 - Nov 16
Total with taxes and fees
Country Rose Cottage

11. 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 15 - Nov 16
Total with taxes and fees
Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast

12. 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!

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.
$311 nightly
The price is $366
Nov 30 - Dec 1
Total with taxes and fees
Swordfish Suite DOG friendly- Pup Shed Retreat

14. 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 15 - Nov 16
Total with taxes and fees
Tullahoma Whiskey Trail Base w/ Yard & Fire Pit

15. 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 16 - Nov 17
Total with taxes and fees
Hilltop Cottage • Peaceful Escape Near Nashville • Perfect for Couples & Pets

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.
$318 nightly
The price is $354
Nov 15 - Nov 16
Total with taxes and fees
Stunning Cottage Nestled Amidst Trees with Fire Pit in Monteagle, Tennessee

17. 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.
$348 nightly
The price is $410
Nov 15 - Nov 16
Total with taxes and fees
Peaceful Mountaintop Cottage

18. 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!

19. Magical Tiny Cottage with Lovely Outdoor Living in Tennessee

Magical Tiny Cottage with Lovely Outdoor Living in Tennessee
Tracy City
$346 nightly
The price is $400
Nov 16 - Nov 17
Total with taxes and fees
Magical Tiny Cottage with Lovely Outdoor Living in Tennessee

20. Outstanding Cottage with Stunning Sights in Monteagle, Tennessee

Outstanding Cottage with Stunning Sights in Monteagle, Tennessee
Monteagle
$313 nightly
The price is $348
Dec 1 - Dec 2
Total with taxes and fees
Outstanding Cottage with Stunning Sights in Monteagle, 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

Find out more about Winchester

Winchester Cottages information

Number of reviews
120
Accommodation
77 Cottages
Lowest Price
$168
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.

Explore a world of travel with Expedia