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

Search Cottages in Winchester

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

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.
The price is AED 408
AED 752 total
includes taxes & fees
19 Nov - 20 Nov
Tiny Home w/ RV Hookups

2. 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 AED 320
AED 759 total
includes taxes & fees
19 Nov - 20 Nov
Cozy Cottage in Monteagle!

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 AED 320
AED 792 total
includes taxes & fees
8 Nov - 9 Nov
Smarter than the Average Stay at the Yogi Cottage!

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

Lakes, Whiskey & More! Charming Home in Tullahoma
3.0 star property
Tullahoma
The price is AED 507
AED 1,385 total
includes taxes & fees
16 Nov - 17 Nov
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.
The price is AED 298
AED 770 total
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 AED 405
AED 1,004 total
includes taxes & fees
8 Nov - 9 Nov
Catch Some ZZZ's at the Grizzly Cottage

7. 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 AED 430
AED 757 total
includes taxes & fees
6 Nov - 7 Nov
Country Rose Cottage

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 AED 320
AED 792 total
includes taxes & fees
8 Nov - 9 Nov
Have the Sweetest Dreams @ the Honey Bear Cottage!

9. 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 AED 771
AED 1,167 total
includes taxes & fees
6 Nov - 7 Nov
Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast

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 AED 320
AED 792 total
includes taxes & fees
8 Nov - 9 Nov
Visit 100 Aker Woods and Stay at Winnie Cottage!

11. 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 AED 459
AED 716 total
includes taxes & fees
6 Dec - 7 Dec
Adorable 1 bedroom tiny home w/ loft situated on 156 acres in Shelbyville, TN

12. 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 AED 459
AED 755 total
includes taxes & fees
6 Dec - 7 Dec
Hilltop Cottage • Peaceful Escape Near Nashville • Perfect for Couples & Pets

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 AED 826
AED 1,446 total
includes taxes & fees
7 Nov - 8 Nov
Peaceful Mountaintop Cottage

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

Tullahoma Whiskey Trail Base w/ Yard & Fire Pit
3.0 star property
Tullahoma
The price is AED 709
AED 1,885 total
includes taxes & fees
8 Nov - 9 Nov
Tullahoma Whiskey Trail Base w/ Yard & Fire Pit

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

Only You Can Stay at the Smokey the Bear Cottage!
Monteagle
The price is AED 320
AED 777 total
includes taxes & fees
8 Nov - 9 Nov
Only You Can Stay at the Smokey the Bear Cottage!

16. 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 AED 500
AED 1,341 total
includes taxes & fees
9 Nov - 10 Nov
Swordfish Suite DOG friendly- Pup Shed Retreat

17. 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 AED 1,017
AED 1,291 total
includes taxes & fees
30 Nov - 1 Dec
Stunning Cottage Nestled Amidst Trees with Fire Pit in Monteagle, Tennessee

18. Outstanding Cottage with Stunning Sights in Monteagle, Tennessee

Outstanding Cottage with Stunning Sights in Monteagle, Tennessee
Monteagle
The price is AED 998
AED 1,274 total
includes taxes & fees
9 Nov - 10 Nov
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 AED 1,102
AED 1,459 total
includes taxes & fees
9 Nov - 10 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 AED 1,057
AED 1,399 total
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

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.

Explore a world of travel with Expedia