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Nov 14 - Nov 16
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Nov 21 - Nov 23
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Dec 5 - Dec 7
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Jan 2 - Jan 4

Cottages in Winchester

Exterior
Tiny Home w/ RV Hookups
Tiny Home w/ RV Hookups
8.8 out of 10, Excellent, (8)
"Very clean highly recommend if you are looking to get away and relax "
United States
Jeffrey
$219 nightly
The price is $251
Nov 7 - Nov 8
Total with taxes and fees
Tiny Home w/ RV Hookups
Property grounds
Picturesque Tiny Cottage with Cozy Indoor and Outdoor in Tennessee
Picturesque Tiny Cottage with Cozy Indoor and Outdoor in Tennessee
$233 nightly
The price is $263
Nov 6 - Nov 7
Total with taxes and fees
Picturesque Tiny Cottage with Cozy Indoor and Outdoor in Tennessee
Property grounds
Secluded Cottage with Fire Pit in Tracy City, Tennessee
Secluded Cottage with Fire Pit in Tracy City, Tennessee
$244 nightly
The price is $286
Nov 6 - Nov 7
Total with taxes and fees
Secluded Cottage with Fire Pit in Tracy City, Tennessee
Outdoor dining
Outstanding Cottage with Stunning Sights in Monteagle, Tennessee
Outstanding Cottage with Stunning Sights in Monteagle, Tennessee
$259 nightly
The price is $292
Nov 6 - Nov 7
Total with taxes and fees
Outstanding Cottage with Stunning Sights in Monteagle, Tennessee
Property grounds
Breathtaking Cottage with Fire Pit in Tracy City, Tennessee
Breathtaking Cottage with Fire Pit in Tracy City, Tennessee
$264 nightly
The price is $310
Nov 12 - Nov 13
Total with taxes and fees
Breathtaking Cottage with Fire Pit in Tracy City, Tennessee
Exterior
Impressive Cottage with Barbecue in Monteagle, Tennessee
Impressive Cottage with Barbecue in Monteagle, Tennessee
$251 nightly
The price is $282
Nov 11 - Nov 12
Total with taxes and fees
Impressive Cottage with Barbecue in Monteagle, Tennessee
Exterior
Fantastic Cozy Cottage Nestled Amidst Trees in Tracy City, Tennessee
Fantastic Cozy Cottage Nestled Amidst Trees in Tracy City, Tennessee
$347 nightly
The price is $407
Nov 6 - Nov 7
Total with taxes and fees
Fantastic Cozy Cottage Nestled Amidst Trees in Tracy City, Tennessee
Exterior
Visit 100 Aker Woods and Stay at Winnie Cottage!
Visit 100 Aker Woods and Stay at Winnie Cottage!
10.0 out of 10, Exceptional, (11)
"My stay at the Winnie Cabin in Monteagle was exactly what I needed—quiet, clean, and beautifully furnished. Tucked away in a peaceful setting, the cabin offered a perfect balance of comfort and charm. Every detail was thoughtfully curated, from the cozy décor to the spotless interior. It felt like a true retreat—a place to slow down, breathe deeply, and simply enjoy the quiet. I left feeling refreshed, grounded, and already planning my next visit. Thank you! "
United States
Charlene S.
$156 nightly
The price is $156
Nov 6 - Nov 7
Total with taxes and fees
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
9.6 out of 10, Exceptional, (5)
"Our family enjoyed a simple low-key stay after catching a show nearby and appreciated the no-frills experience overall. Pricing was great and would not hesitate to stay here again."
United States
Will
$171 nightly
The price is $188
Nov 6 - Nov 7
Total with taxes and fees
Catch Some ZZZ's at the Grizzly Cottage
Exterior
Swordfish Suite DOG friendly- Pup Shed Retreat
Swordfish Suite DOG friendly- Pup Shed Retreat
10.0 out of 10, Exceptional, (14)
"My family had a wonderful time at this tiny house (which is a bit of a misnomer as we had tons of space for four adults and two children)! The surrounding community is really lovely, and we took advantage of multiple gorgeous hiking trails with waterfall views a very short distance away. All in all, we had a really great time!"
United States
Jennifer L.
$292 nightly
The price is $342
Nov 30 - Dec 1
Total with taxes and fees
Swordfish Suite DOG friendly- Pup Shed Retreat
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
10.0 out of 10, Exceptional, (44)
"Bob and Anita are amazing, they go out of their way to make sure all of your needs are met. Loved the cottage."
United States
TIFFANY D J.
$254 nightly
The price is $287
Nov 6 - Nov 7
Total with taxes and fees
Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast
Exterior
Peaceful Mountaintop Cottage
Peaceful Mountaintop Cottage
9.8 out of 10, Exceptional, (14)
"We enjoyed this spacious home!"
United States
Bradley V.
$429 nightly
The price is $502
Nov 6 - Nov 7
Total with taxes and fees
Peaceful Mountaintop Cottage
Exterior
Smarter than the Average Stay at the Yogi Cottage!
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. "
United States
Rachel C.
$156 nightly
The price is $156
Nov 6 - Nov 7
Total with taxes and fees
Smarter than the Average Stay at the Yogi Cottage!
Exterior
Story-time Stay at Our Rupert Cottage!
Story-time Stay at Our Rupert Cottage!
8.4 out of 10, Very Good, (5)
"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"
United States
Beth L.
$156 nightly
The price is $169
Nov 30 - Dec 1
Total with taxes and fees
Story-time Stay at Our Rupert Cottage!
Terrace/patio
Bluebird Rest - Lakefront Cottage
Bluebird Rest - Lakefront Cottage
10.0 out of 10, Exceptional, (54)
"Great relaxing stay!!"
United States
Brian H.
$395 nightly
The price is $446
Nov 6 - Nov 7
Total with taxes and fees
Bluebird Rest - Lakefront Cottage
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

La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

10/10 Excellent
"Hotel was clean and the beds were super comfy"
Ariel 1-night trip
Posted 3 days ago
La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

Find out more about Winchester

Winchester Cottages information

Number of reviews
113
Accommodation
62 Cottages
Lowest Price
$156
Highest Price
$502

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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