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
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Winchester apartments

Interior

1. Winchester's Premier Downtown Loft!

Winchester's Premier Downtown Loft!
Winchester
9.4 out of 10, Exceptional, (16 reviews)
"It was wonderful and right in the center of downtown winchester. Very clean and beautiful loft and amazing lighting to have long night talks. Truly amazing"
United States
Gianmarco
The price is CA $128
CA $259 total
includes taxes & fees
Aug 19 - Aug 20
Winchester's Premier Downtown Loft!
Coffee/tea maker, fridge, microwave, oven

2. Oasis on the Square

Oasis on the Square
Winchester
9.8 out of 10, Exceptional, (13 reviews)
"Great location on the square with plenty of dining options a short walk away."
United States
possible Amanda H
The price is CA $136
CA $268 total
includes taxes & fees
Aug 25 - Aug 26
Oasis on the Square
Exterior

3. New Listing! Welcome to Bear Hollow Retreat!

New Listing! Welcome to Bear Hollow Retreat!
Monteagle
The price is CA $74
CA $243 total
includes taxes & fees
Sep 1 - Sep 2
New Listing! Welcome to Bear Hollow Retreat!
Coffee/tea maker, fridge, microwave, toaster

4. Adorable, Stylish Studio in Monteagle, TN!

Adorable, Stylish Studio in Monteagle, TN!
Monteagle
The price is CA $74
CA $243 total
includes taxes & fees
Sep 1 - Sep 2
Adorable, Stylish Studio in Monteagle, TN!
TV

5. Brand New, Adorable Suite Near the Caverns!

Brand New, Adorable Suite Near the Caverns!
Monteagle
The price is CA $74
CA $243 total
includes taxes & fees
Sep 1 - Sep 2
Brand New, Adorable Suite Near the Caverns!
Living area

6. Lounges at Lynchburg Black House - within walking distance to Jack Daniels!

Lounges at Lynchburg Black House - within walking distance to Jack Daniels!
Lynchburg
10.0 out of 10, Exceptional, (16 reviews)
"Amazing little property!"
United States
Carley H.
The price is CA $187
CA $239 total
includes taxes & fees
Sep 14 - Sep 15
Lounges at Lynchburg Black House - within walking distance to Jack Daniels!
Interior

7. Boutique Suite in Historic Tracy City!

Boutique Suite in Historic Tracy City!
Tracy City
10.0 out of 10, Exceptional, (4 reviews)
"Awesome place"
United States
Casey C.
The price is CA $56
CA $160 total
includes taxes & fees
Aug 24 - Aug 25
Boutique Suite in Historic Tracy City!
Terrace/patio

8. Newly Remodled Suite in Monteagle TN!

Newly Remodled Suite in Monteagle TN!
Monteagle
9.4 out of 10, Exceptional, (12 reviews)
"comfy and cute stay!"
United States
Kylee
The price is CA $74
CA $243 total
includes taxes & fees
Sep 2 - Sep 3
Newly Remodled Suite in Monteagle TN!
Smart TV

9. D-town w/ Balcony. Walk to Shops & Eats.

D-town w/ Balcony. Walk to Shops & Eats.
Fayetteville
10.0 out of 10, Exceptional, (6 reviews)
"Great stay!"
United States
Donna R.
The price is CA $123
CA $246 total
includes taxes & fees
Aug 19 - Aug 20
D-town w/ Balcony. Walk to Shops & Eats.
Interior

10. The Pythian Building Penthouse Apt. is centrally located on the city square.

The Pythian Building Penthouse Apt. is centrally located on the city square.
Fayetteville
10.0 out of 10, Exceptional, (51 reviews)
"The penthouse is a fantastical property, we enjoyed our stay very much."
United States
Jinny
The price is CA $193
CA $253 total
includes taxes & fees
Aug 26 - Aug 27
The Pythian Building Penthouse Apt. is centrally located on the city square.
Coffee/tea maker, fridge, microwave, oven

11. Luxury Loft DWTN | Whiskey Trail + River + Lake

Luxury Loft DWTN | Whiskey Trail + River + Lake
Fayetteville
9.8 out of 10, Exceptional, (10 reviews)
"The host was great and the loft was beautiful "
United States
Kitty O.
The price is CA $181
CA $331 total
includes taxes & fees
Aug 19 - Aug 20
Luxury Loft DWTN | Whiskey Trail + River + Lake
2 bedrooms, desk, iron/ironing board, travel crib

12. “Give My All for Tennessee” in Downtown Fayetteville Near Jack Daniels

“Give My All for Tennessee” in Downtown Fayetteville Near Jack Daniels
Fayetteville
10.0 out of 10, Exceptional, (3 reviews)
"Excellent downtown property!!! Close to everything. "
United States
Scotty L.
The price is CA $250
CA $371 total
includes taxes & fees
Aug 20 - Aug 21
“Give My All for Tennessee” in Downtown Fayetteville Near Jack Daniels
TV

13. Centrally located in Shelbyville, just 1/4 mile from the Horse Show Grounds.

Centrally located in Shelbyville, just 1/4 mile from the Horse Show Grounds.
Shelbyville
9.6 out of 10, Exceptional, (19 reviews)
"The place had a very cozy feel. Easy to access and it felt welcoming!"
United States
Kimmi G.
The price is CA $149
CA $260 total
includes taxes & fees
Aug 19 - Aug 20
Centrally located in Shelbyville, just 1/4 mile from the Horse Show Grounds.
Smart TV, video games

14. Cozy 2-bedroom apartment in charming downtown South Pittsburg, TN

Cozy 2-bedroom apartment in charming downtown South Pittsburg, TN
South Pittsburg
9.0 out of 10, Wonderful, (4 reviews)
"Located in a small, old and run down part of town. It’s ok if you want something inexpensive but not fancy. Host was nice."
United States
Kim H.
The price is CA $128
CA $210 total
includes taxes & fees
Sep 5 - Sep 6
Cozy 2-bedroom apartment in charming downtown South Pittsburg, TN
Interior

15. Sleeps 6. Two Downtown Lofts Combined.

Sleeps 6. Two Downtown Lofts Combined.
Fayetteville
10.0 out of 10, Exceptional, (2 reviews)
"Our girlfriend group loved this little getaway on the square. It was such a treat to come back and relax in the larger loft space after checking out downtown’s shops and eats. Hospitality was extended by the hosts and everyone we encountered in Fayetteville. A wonderful stay!"
United States
Eileen G.
The price is CA $229
CA $455 total
includes taxes & fees
Aug 19 - Aug 20
Sleeps 6. Two Downtown Lofts Combined.
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

Best Western Inn

Best Western Inn

10/10 Excellent
"Great staff and the breakfast items were hot and good"
William 2-night trip
Posted 3 days ago
Best Western Inn

Find out more about Winchester

Winchester Apartments information

Number of reviews
156
Accommodation
29 Apartments
Lowest Price
CA $160
Highest Price
CA $455

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You'll find 8 apartments to choose from in Winchester for your vacation.
Are you thinking about apartments over traditional hotel rooms?
Offering a kitchen for convenient meals, an apartment often has more space than a traditional hotel room. Apartments are a good option for solo travelers who want to live like locals, but also for families wanting the conveniences of home.
What's the best apartment for a stay in Winchester?
Winchester's Premier Downtown Loft!: Includes fireplaces and separate dining areas. Access to onsite laundry facilities is available on site. Dry Jack Tim-Hot Tub, Water Views, Marina: Free WiFi and fireplaces are included. Onsite laundry facilities and a hot tub are on site. Lakeside Retreat with Golf Cart, Game Room, Fireplace, Pool: Includes free WiFi, fireplaces, and sofa beds. Onsite laundry facilities and a game room are on site. Best Views on Lake, TIki Hut, Boat Rental: Free WiFi, private balconies, and fireplaces are included. Onsite laundry facilities and a game room are on site.
How many apartments can I expect to find in Winchester?
Expedia has 8 apartments to book in Winchester.
What can I expect from the weather in Winchester?
Weather is only one factor, but it can really affect your travel plans, especially if you're planning an extended stay in Winchester. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 43°F. Average annual precipitation for Winchester is 64 inches.
What are the must-see places to visit in Winchester?
Family-friendly attractions include Twin Creeks Marina and Tim's Ford Marina, whereas Tims Ford Lake and Elk River are a couple of great spots to enjoy the outdoors. While here, Tims Ford State Park and Franklin County Farmers Market are other places worth a visit.
What's the best way to get to and around Winchester?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Chattanooga Metropolitan Airport (CHA), which is located 52.8 mi (85 km) away from the city center. Otherwise, you can search for flights to Huntsville International Airport (HSV), which is 52.8 mi (85 km) away. If you'd like to explore around the area, you may want a rental car for your journey.

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