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

Apartments in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Winchester apartments

Coffee/tea maker, fridge, microwave, oven

1. 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 AU$274
includes taxes & fees
7 Sept - 8 Sept
Oasis on the Square
Interior

2. 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 AU$284
includes taxes & fees
7 Sept - 8 Sept
Winchester's Premier Downtown Loft!
Exterior

3. New Listing! Welcome to Bear Hollow Retreat!

New Listing! Welcome to Bear Hollow Retreat!
Monteagle
The price is AU$247
includes taxes & fees
2 Sept - 3 Sept
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 AU$249
includes taxes & fees
2 Sept - 3 Sept
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 AU$249
includes taxes & fees
2 Sept - 3 Sept
Brand New, Adorable Suite Near the Caverns!
Terrace/patio

6. 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 AU$247
includes taxes & fees
8 Sept - 9 Sept
Newly Remodled Suite in Monteagle TN!
Living area

7. 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, (19 reviews)
"Very friendly host , clean and neat , great location. We had a great time and hope to come back . "
United States
Brian S.
The price is AU$248
includes taxes & fees
7 Sept - 8 Sept
Lounges at Lynchburg Black House - within walking distance to Jack Daniels!
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 AU$197
includes taxes & fees
15 Sept - 16 Sept
Boutique Suite in Historic Tracy City!
Smart TV, video games

9. 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 AU$208
includes taxes & fees
5 Sept - 6 Sept
Cozy 2-bedroom apartment in charming downtown South Pittsburg, TN
Smart TV, books

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

Luxury Loft DWTN | Whiskey Trail + River + Lake
Fayetteville
10.0 out of 10, Exceptional, (11 reviews)
"The host was great and the loft was beautiful "
United States
Kitty O.
The price is AU$317
includes taxes & fees
14 Sept - 15 Sept
Luxury Loft DWTN | Whiskey Trail + River + Lake
Interior

11. 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 AU$263
includes taxes & fees
10 Sept - 11 Sept
The Pythian Building Penthouse Apt. is centrally located on the city square.
Smart TV

12. 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 AU$261
includes taxes & fees
29 Sept - 30 Sept
D-town w/ Balcony. Walk to Shops & Eats.
2 bedrooms, desk, iron/ironing board, travel cot

13. “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 AU$373
includes taxes & fees
2 Sept - 3 Sept
“Give My All for Tennessee” in Downtown Fayetteville Near Jack Daniels
TV

14. 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 AU$303
includes taxes & fees
6 Sept - 7 Sept
Centrally located in Shelbyville, just 1/4 mile from the Horse Show Grounds.
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 AU$459
includes taxes & fees
7 Sept - 8 Sept
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.
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

Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

10/10 Excellent
"This is our 3rd time to stay here. We love the location."
Cheri J. 3-night trip
Posted 12 days ago
Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

Find out more about Winchester

Winchester Apartments information

Number of reviews
145
Accommodation
30 Apartments
Lowest Price
AU$197
Highest Price
AU$459

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 holiday.
Are you thinking about apartments over traditional hotel rooms?
An apartment features a kitchen for convenient meals, and is usually more spacious than a traditional hotel room. Apartments are a good option for couples who want to live like locals, but also for families wanting the conveniences of home.
What's a favourite apartment for a stay in Winchester?
Dry Jack Tim-Hot Tub, Water Views, Marina: Includes free WiFi and a fireplace . On-site laundry facilities and 1 hot tub are on site . Winchester's Premier Downtown Loft!: A fireplace and a dining area are included . Access to on-site laundry facilities is available on site . Lakeside Retreat with Golf Cart, Game Room, Fireplace, Pool: Includes free WiFi, a fireplace and a sofa bed . On-site laundry facilities and a games room are on site . Best Views on Lake, TIki Hut, Boat Rental: Includes free WiFi, a balcony and a fireplace . On-site laundry facilities and a games 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 during my trip to 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 temperature of 24°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Winchester is 1622 mm.
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 Hammers 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, TN (CHA-Chattanooga Metropolitan), which is located 52.8 mi (85 km) away from the heart of the city. 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.