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Sep 26 - Sep 28
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Cottages in Winchester

Our top choices for Winchester cottages

The Blue Heron - Lake Side Chalet
Property grounds

The Blue Heron - Lake Side Chalet

10.0 out of 10, Exceptional, (95)
"Beautiful home, wonderful view, great host. Highly recommended!"
The Blue Heron - Lake Side Chalet
Holiday Cottage at Tim's Ford Lake next to Marina and Restaurant
Outdoor dining

Holiday Cottage at Tim's Ford Lake next to Marina and Restaurant

10.0 out of 10, Exceptional, (35)
"This place was so clean, super comfortable beds, and great location. Host was fantastic! Will definitely come back!"
Holiday Cottage at Tim's Ford Lake next to Marina and Restaurant
Snuggle Up in our Teddy Cottage! *New Listing*
Exterior

Snuggle Up in our Teddy Cottage! *New Listing*

10.0 out of 10, Exceptional, (6)
"Property was just as described and photographed. Sometimes that can be disappointing.Loved the attention to detail in the decor and including all essentials.It was very quiet and safe.Would recommend this property to others!"
$156 nightly
The price is $156
Sep 22 - Sep 23
Total with taxes and fees
Snuggle Up in our Teddy Cottage! *New Listing*
Bluebird Rest - Lakefront Cottage
Terrace/patio

Bluebird Rest - Lakefront Cottage

10.0 out of 10, Exceptional, (52)
"This was the best hidden gem we have came across. Beautiful house in a perfect location. The host of this property was amazing and very hospitable. They get 10s all across the board. "
$395 nightly
The price is $446
Sep 22 - Sep 23
Total with taxes and fees
Bluebird Rest - Lakefront Cottage
Story-time Stay at Our Rupert Cottage!
Exterior

Story-time Stay at Our Rupert Cottage!

10.0 out of 10, Exceptional, (2)
"Loved staying here. The staff, the cabin, the atmosphere were perfect for this weary traveler! It was great having the consistentcy of the cabin to stay at while seeking my forevervhome in Nashville! I am so grateful"
$156 nightly
The price is $169
Sep 29 - Sep 30
Total with taxes and fees
Story-time Stay at Our Rupert Cottage!
“License To Chill”. Lake Cottage at Tims Ford Lake Golf cart/Fire pit/Marina
Property grounds

“License To Chill”. Lake Cottage at Tims Ford Lake Golf cart/Fire pit/Marina

10.0 out of 10, Exceptional, (15)
"Great view, quiet and secluded deck, great floor plan."
“License To Chill”. Lake Cottage at Tims Ford Lake Golf cart/Fire pit/Marina
Lake it Oar Leave it- Lake front Tim's Ford Lake with DOCK
Property grounds

Lake it Oar Leave it- Lake front Tim's Ford Lake with DOCK

9.8 out of 10, Exceptional, (28)
"Clean, and accurate listing. "
Lake it Oar Leave it- Lake front Tim's Ford Lake with DOCK
Historic 1940's Cottage Near Tim's Ford Lake & Town Square Fully Remodeled
Exterior

Historic 1940's Cottage Near Tim's Ford Lake & Town Square Fully Remodeled

2.0 star property
10.0 out of 10, Exceptional, (5)
"Used for work housing "
Historic 1940's Cottage Near Tim's Ford Lake & Town Square Fully Remodeled
Tiny Home w/ RV Hookups
Exterior

Tiny Home w/ RV Hookups

8.4 out of 10, Very Good, (6)
"Perfect little spot, nice tiny home. Would stay again."
$217 nightly
The price is $249
Sep 23 - Sep 24
Total with taxes and fees
Tiny Home w/ RV Hookups
Cozy family friendly 2 bedroom lakefront cottage in charming Tracy City TN
Outdoor dining

Cozy family friendly 2 bedroom lakefront cottage in charming Tracy City TN

Cozy family friendly 2 bedroom lakefront cottage in charming Tracy City TN
The Livery at Rainbows End
Outdoor dining

The Livery at Rainbows End

10.0 out of 10, Exceptional, (4)
"This was a great little bungalow. "
The Livery at Rainbows End
Charming cottage in wooded location
Terrace/patio

Charming cottage in wooded location

10.0 out of 10, Exceptional, (31)
"We've stayed in this adorable cottage several times and it is always a pleasure. Close to Sewanee campus, while also being cozily secluded. "
Charming cottage in wooded location
Hollerback Hunt & Yacht Club, peaceful lakefront with private dock on 6 Acres
Exterior

Hollerback Hunt & Yacht Club, peaceful lakefront with private dock on 6 Acres

9.6 out of 10, Exceptional, (130)
"What a beautiful county oasis. And....we caught 25-30 fish including a lot of fun sized bass. Perfect for kids fishing! "
Hollerback Hunt & Yacht Club, peaceful lakefront with private dock on 6 Acres
Catch Some ZZZ's at the Grizzly Cottage
Exterior

Catch Some ZZZ's at the Grizzly Cottage

9.6 out of 10, Exceptional, (4)
"Very comfortable and clean, close to hiking trails. We enjoyed our stay very much!"
$171 nightly
The price is $188
Sep 22 - Sep 23
Total with taxes and fees
Catch Some ZZZ's at the Grizzly Cottage
Visit 100 Aker Woods and Stay at Winnie Cottage!
Exterior

Visit 100 Aker Woods and Stay at Winnie Cottage!

10.0 out of 10, Exceptional, (11)
"Spent the night here while travelking south. The place was perfect for what we needed!"
$156 nightly
The price is $156
Sep 22 - Sep 23
Total with taxes and fees
Visit 100 Aker Woods and Stay at Winnie Cottage!
Lakeside Cottage Retreat at Tim's Ford Lake
Property grounds

Lakeside Cottage Retreat at Tim's Ford Lake

10.0 out of 10, Exceptional, (35)
"We came in for the weekend. The location was walking distance from a restaurant in the lake. It was great! "
Lakeside Cottage Retreat at Tim's Ford Lake
Cottage by the creek, beautiful Mountain View, perfect getaway!!!
Exterior

Cottage by the creek, beautiful Mountain View, perfect getaway!!!

10.0 out of 10, Exceptional, (44)
"Everything was clean and the views were amazing! We really enjoyed our stay here and will definitely be coming back."
Cottage by the creek, beautiful Mountain View, perfect getaway!!!
Smarter than the Average Stay at the Yogi Cottage!
Exterior

Smarter than the Average Stay at the Yogi Cottage!

8.8 out of 10, Excellent, (6)
"We stayed the night to enjoy a concert at the Caverns. The cottage is adorable and the Caverns are amazing. "
$156 nightly
The price is $156
Sep 29 - Sep 30
Total with taxes and fees
Smarter than the Average Stay at the Yogi Cottage!
Swordfish Suite DOG friendly- Pup Shed Retreat
Exterior

Swordfish Suite DOG friendly- Pup Shed Retreat

10.0 out of 10, Exceptional, (10)
"Very dog and family friendly. Enjoyed our stay. Perfect location!"
$292 nightly
The price is $342
Sep 22 - Sep 23
Total with taxes and fees
Swordfish Suite DOG friendly- Pup Shed Retreat
Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast
Exterior

Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast

10.0 out of 10, Exceptional, (44)
"Beautiful property and wonderful proprietors."
$256 nightly
The price is $289
Sep 22 - Sep 23
Total with taxes and fees
Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast
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

Quality Inn Tullahoma

Quality Inn Tullahoma

10/10 Excellent
"Clean room. Zero frills. Friendly staff, "
Sandy 1-night trip
Posted 2 days ago
Quality Inn Tullahoma

Find out more about Winchester

Find out more about Winchester

Winchester Cottages information

Number of reviews
505
Accommodation
68 Cottages
Lowest Price
$156
Highest Price
$446

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