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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Winchester apartments

A modern living room with a built-in aquarium, a leather sofa, and a patterned rug.

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 £153
includes taxes & fees
7 Sept - 8 Sept
Winchester's Premier Downtown Loft!
A modern kitchen with dark cabinetry, stainless steel appliances, and a light-colored backsplash.

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 £146
includes taxes & fees
31 Aug - 1 Sept
Oasis on the Square
A modern living room with a black leather sofa, a brown leather armchair, and a small side table.

3. 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, (18 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 £133
includes taxes & fees
7 Sept - 8 Sept
Lounges at Lynchburg Black House - within walking distance to Jack Daniels!
A wooden deck with two Adirondack chairs and a table, a covered porch, and a door with a number.

4. 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 £134
includes taxes & fees
3 Sept - 4 Sept
Newly Remodled Suite in Monteagle TN!
A hallway with wooden doors labeled 'The Cove' and 'The Overlook,' leading to a room with a view.

5. 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 £89
includes taxes & fees
31 Aug - 1 Sept
Boutique Suite in Historic Tracy City!
A rustic building with a red roof and a wooden facade, likely a barn or historical building.

6. New Listing! Welcome to Bear Hollow Retreat!

New Listing! Welcome to Bear Hollow Retreat!
Monteagle
The price is £132
includes taxes & fees
1 Sept - 2 Sept
New Listing! Welcome to Bear Hollow Retreat!

7. Adorable, Stylish Studio in Monteagle, TN!

Adorable, Stylish Studio in Monteagle, TN!
Monteagle
The price is £134
includes taxes & fees
1 Sept - 2 Sept
Adorable, Stylish Studio in Monteagle, TN!
A modern living room with a sofa, a TV, a wooden cabinet, and a kitchen area with a microwave and cabinets.

8. Brand New, Adorable Suite Near the Caverns!

Brand New, Adorable Suite Near the Caverns!
Monteagle
The price is £134
includes taxes & fees
1 Sept - 2 Sept
Brand New, Adorable Suite Near the Caverns!
A spacious living room with a sofa, armchairs, and a patterned rug. A kitchen is visible in the background with modern appliances.

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 £156
includes taxes & fees
2 Sept - 3 Sept
D-town w/ Balcony. Walk to Shops & Eats.
A room with a fireplace, a large statue, and a variety of decorative items.

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 £193
includes taxes & fees
11 Sept - 12 Sept
The Pythian Building Penthouse Apt. is centrally located on the city square.
A compact living space with a sofa, a small table, a kitchenette with a refrigerator and microwave, and a sliding door leading to another room.

11. 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 £119
includes taxes & fees
5 Sept - 6 Sept
Cozy 2-bedroom apartment in charming downtown South Pittsburg, TN
A modern kitchen with white cabinets, a black countertop, and a wooden floor.

12. 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 £172
includes taxes & fees
14 Sept - 15 Sept
Luxury Loft DWTN | Whiskey Trail + River + Lake
A room with a brick wall, a bed with colorful pillows, a desk with a lamp, and a door.

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 £198
includes taxes & fees
31 Aug - 1 Sept
“Give My All for Tennessee” in Downtown Fayetteville Near Jack Daniels
A modern living room with a grey leather sofa, two round marble tables, and a TV on a stand.

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 £163
includes taxes & fees
6 Sept - 7 Sept
Centrally located in Shelbyville, just 1/4 mile from the Horse Show Grounds.
A spacious kitchen with modern appliances, a dining area with a large wooden table, and a living room with a sofa and a TV.

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 £242
includes taxes & fees
1 Sept - 2 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.
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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 10 days ago
Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

Find out more about Winchester

Winchester Apartments information

Number of reviews
159
Accommodation
30 Apartments
Lowest Price
£89
Highest Price
£242

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.