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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Winchester apartments

Interior

1. Winchester's Premier Downtown Loft!

Winchester's Premier Downtown Loft!
Winchester
9.6 out of 10, Exceptional, (17 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 $117
CA $247 total
includes taxes & fees
Sep 16 - Sep 17
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 $270 total
includes taxes & fees
Sep 27 - Sep 28
Oasis on the Square
TV

3. New Listing! Welcome to Bear Hollow Retreat!

New Listing! Welcome to Bear Hollow Retreat!
Monteagle
The price is CA $96
CA $266 total
includes taxes & fees
Sep 17 - Sep 18
New Listing! Welcome to Bear Hollow Retreat!
Internet, bed sheets

4. Brand New, Adorable Suite Near the Caverns!

Brand New, Adorable Suite Near the Caverns!
Monteagle
The price is CA $96
CA $269 total
includes taxes & fees
Sep 17 - Sep 18
Brand New, Adorable Suite Near the Caverns!
Terrace/patio

5. 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 $96
CA $269 total
includes taxes & fees
Sep 17 - Sep 18
Newly Remodled Suite in Monteagle TN!
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, (21 reviews)
"This place was awesome the host was also outstanding no matter the question she was very informative and always available when asked something.This is a great place to stay when doing the Jack Daniels Tours."
United States
Frederick E.
The price is CA $187
CA $244 total
includes taxes & fees
Oct 1 - Oct 2
Lounges at Lynchburg Black House - within walking distance to Jack Daniels!
Coffee/tea maker, fridge, microwave, toaster

7. Adorable, Stylish Studio in Monteagle, TN!

Adorable, Stylish Studio in Monteagle, TN!
Monteagle
The price is CA $96
CA $269 total
includes taxes & fees
Sep 17 - Sep 18
Adorable, Stylish Studio in Monteagle, TN!
Interior

8. 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 $83
CA $194 total
includes taxes & fees
Sep 22 - Sep 23
Boutique Suite in Historic Tracy City!
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, (7 reviews)
"Great stay!"
United States
Donna R.
The price is CA $141
CA $267 total
includes taxes & fees
Sep 16 - Sep 17
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, (52 reviews)
"The penthouse is a fantastical property, we enjoyed our stay very much."
United States
Jinny
The price is CA $193
CA $258 total
includes taxes & fees
Oct 1 - Oct 2
The Pythian Building Penthouse Apt. is centrally located on the city square.
WiFi (free), bed sheets

11. Cozy 1-bedroom apartment in adorable Fayetteville Near Jack Daniel's!

Cozy 1-bedroom apartment in adorable Fayetteville Near Jack Daniel's!
Fayetteville
The price is CA $129
CA $248 total
includes taxes & fees
Sep 22 - Sep 23
Cozy 1-bedroom apartment in adorable Fayetteville Near Jack Daniel's!
TV

12. 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, (20 reviews)
"The place had a very cozy feel. Easy to access and it felt welcoming!"
United States
Kimmi G.
The price is CA $174
CA $297 total
includes taxes & fees
Sep 20 - Sep 21
Centrally located in Shelbyville, just 1/4 mile from the Horse Show Grounds.
Interior

13. 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 $216
CA $437 total
includes taxes & fees
Sep 16 - Sep 17
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

Dock, Water Views, Kayaks, Fire Pit, Game Room

Dock, Water Views, Kayaks, Fire Pit, Game Room

10/10 Excellent
"This was a great house for our vacation, It was very clean and had everything we needed. We were treated very well by the property mangers and would definitely use them again."
MIKE K. 7-night trip
Posted 18 hours ago
Dock, Water Views, Kayaks, Fire Pit, Game Room

Find out more about Winchester

Winchester Apartments information

Number of reviews
6,502
Accommodation
29 Apartments
Lowest Price
CA $81
Highest Price
CA $326

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?
Dry Jack Tim-Hot Tub, Water Views, Marina: Includes free WiFi and fireplaces. Onsite laundry facilities and a hot tub are on site. Winchester's Premier Downtown Loft!: Fireplaces and separate dining areas are included. Access to onsite laundry facilities is available 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 and Tims Ford Lake are a couple of great spots to enjoy the outdoors. While here, Tims Ford State Park and Elk River 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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