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
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Winchester cottages

Exterior

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 HK$825
HK$1,679 total
includes taxes & fees
27 Jul - 28 Jul
Tiny Home w/ RV Hookups
Exterior

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 HK$1,646
HK$2,600 total
includes taxes & fees
17 Jul - 18 Jul
Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast
Interior

Lakes, Whiskey & More! Charming Home in Tullahoma

Lakes, Whiskey & More! Charming Home in Tullahoma
3.0 star property
Tullahoma
The price is HK$988
HK$2,844 total
includes taxes & fees
18 Jul - 19 Jul
Lakes, Whiskey & More! Charming Home in Tullahoma
Exterior

Peaceful Mountaintop Cottage

Peaceful Mountaintop Cottage
Tracy City
9.8 out of 10, Exceptional, (18 reviews)
"This is the cutest house! We rented it for a little staycation girls night and it was a perfect experience. We would definitely come back!"
United States
Emily F.
The price is HK$2,234
HK$3,959 total
includes taxes & fees
29 Jul - 30 Jul
Peaceful Mountaintop Cottage
Property grounds

Picturesque Tiny Cottage with Cozy Indoor and Outdoor in Tennessee

Picturesque Tiny Cottage with Cozy Indoor and Outdoor in Tennessee
Monteagle
The price is HK$2,008
HK$2,468 total
includes taxes & fees
29 Jul - 30 Jul
Picturesque Tiny Cottage with Cozy Indoor and Outdoor in Tennessee
Exterior

Fantastic Cozy Cottage Nestled Amidst Trees in Tracy City, Tennessee

Fantastic Cozy Cottage Nestled Amidst Trees in Tracy City, Tennessee
Tracy City
The price is HK$2,375
HK$3,124 total
includes taxes & fees
28 Jul - 29 Jul
Fantastic Cozy Cottage Nestled Amidst Trees in Tracy City, Tennessee
Exterior

Stunning Cottage Nestled Amidst Trees with Fire Pit in Monteagle, Tennessee

Stunning Cottage Nestled Amidst Trees with Fire Pit in Monteagle, Tennessee
Monteagle
The price is HK$2,050
HK$2,579 total
includes taxes & fees
29 Jul - 30 Jul
Stunning Cottage Nestled Amidst Trees with Fire Pit in Monteagle, Tennessee
Terrace/patio

Bluebird Rest - Peaceful Lake Retreat

Bluebird Rest - Peaceful Lake Retreat
Kelso
10.0 out of 10, Exceptional, (68 reviews)
"Adorable cottage on a quiet lake. The house was perfect, with comfortable furniture and a well stocked kitchen. The host was very kind and responsive when needed. We enjoyed our time & would look to stay again in the future!"
United States
Jennifer H.
The price is HK$1,842
HK$3,343 total
includes taxes & fees
3 Aug - 4 Aug
Bluebird Rest - Peaceful Lake Retreat
Outdoor dining

Cozy Cottage in Monteagle!

Cozy Cottage in Monteagle!
Monteagle
10.0 out of 10, Exceptional, (1 review)
The price is HK$503
HK$1,561 total
includes taxes & fees
19 Jul - 20 Jul
Cozy Cottage in Monteagle!
Outdoor dining

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, (6 reviews)
The price is HK$889
HK$1,423 total
includes taxes & fees
20 Jul - 21 Jul
Adorable 1 bedroom tiny home w/ loft situated on 156 acres in Shelbyville, TN
Exterior

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, (12 reviews)
"I enjoyed my time on Monteagle at the Winnie cottage. It was a great time to rest and recharge. "
United States
Ashli L.
The price is HK$503
HK$1,561 total
includes taxes & fees
19 Jul - 20 Jul
Visit 100 Aker Woods and Stay at Winnie Cottage!
Exterior

Catch Some ZZZ's at the Grizzly Cottage

Catch Some ZZZ's at the Grizzly Cottage
Monteagle
9.8 out of 10, Exceptional, (10 reviews)
"Just right for an overnight stay for our family of five. Even though it overall is a small space, having two bathrooms and enough sleeping space for everyone was really nice. "
United States
Caitlin L.
The price is HK$503
HK$1,790 total
includes taxes & fees
23 Jul - 24 Jul
Catch Some ZZZ's at the Grizzly Cottage
Exterior

Swordfish Suite DOG friendly- Pup Shed Retreat

Swordfish Suite DOG friendly- Pup Shed Retreat
Tracy City
10.0 out of 10, Exceptional, (18 reviews)
"Oh my goodness we BEYOND enjoyed our stay! The Host’s were so wonderful and the atmosphere was great!! Can’t wait to go back again this summer!! Thank to again!! "
United States
Maggie R.
The price is HK$1,066
HK$2,995 total
includes taxes & fees
5 Aug - 6 Aug
Swordfish Suite DOG friendly- Pup Shed Retreat
Exterior

Country Rose Cottage

Country Rose Cottage
Tracy City
10.0 out of 10, Exceptional, (1 review)
"We loved the cute cottage. So cozy and so convenient!!!!! We will be back !!!"
United States
Melinda S.
The price is HK$917
HK$1,679 total
includes taxes & fees
18 Jul - 19 Jul
Country Rose Cottage
Exterior

Outstanding Cottage with Stunning Sights in Monteagle, Tennessee

Outstanding Cottage with Stunning Sights in Monteagle, Tennessee
Monteagle
The price is HK$1,965
HK$2,475 total
includes taxes & fees
29 Jul - 30 Jul
Outstanding Cottage with Stunning Sights in Monteagle, Tennessee
Exterior

Snuggle Up in our Teddy Cottage! *New Listing*

Snuggle Up in our Teddy Cottage! *New Listing*
Monteagle
10.0 out of 10, Exceptional, (7 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 HK$503
HK$1,576 total
includes taxes & fees
29 Jul - 30 Jul
Snuggle Up in our Teddy Cottage! *New Listing*
Property grounds

Gorgeous Cottage with Fire Pit and Barbecue in Tracy City, Tennessee

Gorgeous Cottage with Fire Pit and Barbecue in Tracy City, Tennessee
Tracy City
The price is HK$2,050
HK$2,634 total
includes taxes & fees
21 Jul - 22 Jul
Gorgeous Cottage with Fire Pit and Barbecue in Tracy City, Tennessee
Exterior

Magical Tiny Cottage with Lovely Outdoor Living in Tennessee

Magical Tiny Cottage with Lovely Outdoor Living in Tennessee
Tracy City
The price is HK$2,161
HK$2,772 total
includes taxes & fees
29 Jul - 30 Jul
Magical Tiny Cottage with Lovely Outdoor Living in Tennessee
Exterior

Smarter than the Average Stay at the Yogi Cottage!

Smarter than the Average Stay at the Yogi Cottage!
Monteagle
9.0 out of 10, Wonderful, (8 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 HK$503
HK$1,569 total
includes taxes & fees
22 Jul - 23 Jul
Smarter than the Average Stay at the Yogi Cottage!
Property grounds

Breathtaking Cottage with Fire Pit in Tracy City, Tennessee

Breathtaking Cottage with Fire Pit in Tracy City, Tennessee
Tracy City
The price is HK$2,085
HK$2,729 total
includes taxes & fees
29 Jul - 30 Jul
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

Lakefront w/Private Dock and Walk to Historic Downtown Winchester!

Lakefront w/Private Dock and Walk to Historic Downtown Winchester!

10/10 Excellent
"Great property all around!"
Josh B. 4-night trip
Posted 1 day ago
Lakefront w/Private Dock and Walk to Historic Downtown Winchester!

Find out more about Winchester

Winchester Cottages information

Number of reviews
Accommodation
72 Cottages
Lowest Price
HK$2,844
Highest Price
HK$2,844

Frequently asked questions

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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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