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

Search Winchester Cottages

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

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 £176
includes taxes & fees
27 Jul - 28 Jul
Tiny Home w/ RV Hookups
Outdoor dining

Story-time Stay at Our Rupert Cottage!

Story-time Stay at Our Rupert Cottage!
Monteagle
8.8 out of 10, Excellent, (6 reviews)
"Pet friendly, host communication was excellent. The cottage was tidy and clean. "
United States
Taroub F.
The price is £161
includes taxes & fees
5 Jul - 6 Jul
Story-time Stay at Our Rupert Cottage!
Outdoor dining

Cozy Cottage in Monteagle!

Cozy Cottage in Monteagle!
Monteagle
10.0 out of 10, Exceptional, (1 review)
The price is £151
includes taxes & fees
5 Jul - 6 Jul
Cozy Cottage in Monteagle!
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)
"The property was just what we were looking for our family vacation. Less than an hour from multiple state parks with waterfalls and Chattanooga."
United States
Chelsea N.
The price is £172
includes taxes & fees
5 Jul - 6 Jul
Catch Some ZZZ's at the Grizzly Cottage
House (3 Bedrooms) | Interior

Lakes, Whiskey & More! Charming Home in Tullahoma

Lakes, Whiskey & More! Charming Home in Tullahoma
3.0 star property
Tullahoma
The price is £257
includes taxes & fees
5 Jul - 6 Jul
Lakes, Whiskey & More! Charming Home in Tullahoma
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 £255
includes taxes & fees
5 Jul - 6 Jul
Cozy Cottage at Lavender Farm near Jack Daniel's Distillery, with breakfast
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 £148
includes taxes & fees
6 Jul - 7 Jul
Snuggle Up in our Teddy Cottage! *New Listing*
Exterior

Country Rose Cottage

Country Rose Cottage
Tracy City
The price is £166
includes taxes & fees
5 Jul - 6 Jul
Country Rose Cottage
Property grounds

Hilltop Cottage • Peaceful Escape Near Nashville • Perfect for Couples & Pets

Hilltop Cottage • Peaceful Escape Near Nashville • Perfect for Couples & Pets
Shelbyville
6.0 out of 10, (2 reviews)
"Property was wonderful and very cozy. Perfect little getaway from everyday life. "
United States
Kathy P.
The price is £136
includes taxes & fees
8 Jul - 9 Jul
Hilltop Cottage • Peaceful Escape Near Nashville • Perfect for Couples & Pets
Exterior

Swordfish Suite DOG friendly- Pup Shed Retreat

Swordfish Suite DOG friendly- Pup Shed Retreat
Tracy City
10.0 out of 10, Exceptional, (17 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 £288
includes taxes & fees
6 Jul - 7 Jul
Swordfish Suite DOG friendly- Pup Shed Retreat
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, (4 reviews)
"It was clean, organized, and quiet. We plan to stay there next year."
United States
Jeff S.
The price is £139
includes taxes & fees
13 Jul - 14 Jul
Adorable 1 bedroom tiny home w/ loft situated on 156 acres in Shelbyville, TN
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 £238
includes taxes & fees
6 Jul - 7 Jul
Picturesque Tiny Cottage with Cozy Indoor and Outdoor in Tennessee
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 £151
includes taxes & fees
5 Jul - 6 Jul
Visit 100 Aker Woods and Stay at Winnie Cottage!
Exterior

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 £151
includes taxes & fees
5 Jul - 6 Jul
Have the Sweetest Dreams @ the Honey Bear Cottage!
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 £381
includes taxes & fees
5 Jul - 6 Jul
Peaceful Mountaintop Cottage
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 £151
includes taxes & fees
8 Jul - 9 Jul
Smarter than the Average Stay at the Yogi 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

By The Pool

By The Pool

10/10 Excellent
"We loved the pool and how close the home was to the lake. All around made for a good trip!"
Katie J. 3-night trip
Posted 1 hour ago
By The Pool

Find out more about Winchester

Winchester Cottages information

Number of reviews
121
Accommodation
76 Cottages
Lowest Price
£136
Highest Price
£381

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.