Apartments in Winchester for Rent

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Find vacation rentals that suit your style

cabin image
Cabins
Cabins
Apartment image
Apartments
Apartments

Check prices for these dates

Next weekend
Nov 13 - Nov 15
In two weeks
Nov 20 - Nov 22
In one month
Dec 4 - Dec 6
In two months
Jan 1 - Jan 3

Our top choices for Winchester apartments

A rustic wooden ceiling with a circular opening and hanging light fixtures.

1. Winchester's Premier Downtown Loft!

Winchester's Premier Downtown Loft!
Winchester
9.6 out of 10, Exceptional, (19 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
$167 nightly
The price is $182
Nov 9 - Nov 10
Total with taxes and fees
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
$161 nightly
The price is $175
Nov 12 - Nov 13
Total with taxes and fees
Oasis on the Square
Living area

3. A quiet getaway.

A quiet getaway.
Winchester
$314 nightly
The price is $363
Nov 11 - Nov 12
Total with taxes and fees
A quiet getaway.
A bedroom with a bed, a ceiling fan, a wall-mounted tree decoration, a nightstand with a lamp, and a painting of a sunflower field.

4. SUNFLOWER TINY HOUSE 3 blocks to Jack Daniel Distillery, close to town square

SUNFLOWER TINY HOUSE 3 blocks to Jack Daniel Distillery, close to town square
Lynchburg
9.8 out of 10, Exceptional, (6 reviews)
"Loved are stay here. Great hosts."
United States
Patricia
$109 nightly
The price is $125
Nov 9 - Nov 10
Total with taxes and fees
SUNFLOWER TINY HOUSE 3 blocks to Jack Daniel Distillery, close to town square
A modern living room with a black leather sofa, a brown leather armchair, and a small side table.

5. 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, (24 reviews)
"Beautiful, and handy for walking to JD. Had excellent lunch in Miss Bobo. Host very friendly."
United Kingdom
Mostyn
$149 nightly
The price is $171
Nov 9 - Nov 10
Total with taxes and fees
Lounges at Lynchburg Black House - within walking distance to Jack Daniels!
A wooden deck with outdoor seating and a covered area with large windows.

6. Newly Remodled Suite in Monteagle TN!

Newly Remodled Suite in Monteagle TN!
Monteagle
9.4 out of 10, Exceptional, (13 reviews)
"A very unique location that was quiet and close enough to everything we wanted."
United States
Tina
$188 nightly
The price is $188
Nov 9 - Nov 10
Total with taxes and fees
Newly Remodled Suite in Monteagle TN!
A rustic interior with a leather sofa, a round wooden table, and a bar area.

7. Boutique Suite in Historic Tracy City!

Boutique Suite in Historic Tracy City!
Tracy City
10.0 out of 10, Exceptional, (5 reviews)
"Awesome place"
United States
Casey C.
$103 nightly
The price is $121
Nov 30 - Dec 1
Total with taxes and fees
Boutique Suite in Historic Tracy City!
A spacious living room with a sofa, armchairs, and a patterned rug. A kitchen is visible in the background with modern appliances.

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

D-town w/ Balcony. Walk to Shops & Eats.
Fayetteville
10.0 out of 10, Exceptional, (8 reviews)
"Great stay!"
United States
Donna R.
$160 nightly
The price is $175
Nov 9 - Nov 10
Total with taxes and fees
D-town w/ Balcony. Walk to Shops & Eats.
A modern apartment with a kitchenette, a dining area, a sofa, a bed, and a ceiling fan.

9. New Listing! Welcome to Bear Hollow Retreat!

New Listing! Welcome to Bear Hollow Retreat!
Monteagle
$188 nightly
The price is $188
Nov 9 - Nov 10
Total with taxes and fees
New Listing! Welcome to Bear Hollow Retreat!
A neatly made bed with white linens, two bedside tables with lamps, a wooden nightstand, and a coat rack.

10. Brand New, Adorable Suite Near the Caverns!

Brand New, Adorable Suite Near the Caverns!
Monteagle
$188 nightly
The price is $188
Nov 9 - Nov 10
Total with taxes and fees
Brand New, Adorable Suite Near the Caverns!
A room with a brick wall, a bed with colorful pillows, a desk with a lamp, and a door.

11. “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, (4 reviews)
"Fantastic location and provided exactly all that we needed for a perfect stay. Very clean and comfortable. Communication with host was perfect. Recommended."
United States
Chad J.
$302 nightly
The price is $308
Nov 12 - Nov 13
Total with taxes and fees
“Give My All for Tennessee” in Downtown Fayetteville Near Jack Daniels
A room with a fireplace, a large statue, and a variety of decorative items.

12. 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, (55 reviews)
"The penthouse is a fantastical property, we enjoyed our stay very much."
United States
Jinny
$134 nightly
The price is $159
Nov 9 - Nov 10
Total with taxes and fees
The Pythian Building Penthouse Apt. is centrally located on the city square.
A compact kitchen with wooden shelves, a sink, and a dishwasher.

13. Adorable, Stylish Studio in Monteagle, TN!

Adorable, Stylish Studio in Monteagle, TN!
Monteagle
$188 nightly
The price is $188
Nov 15 - Nov 16
Total with taxes and fees
Adorable, Stylish Studio in Monteagle, TN!
A spacious room with a large wooden table, white chairs, and a brick wall.

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

Luxury Loft DWTN | Whiskey Trail + River + Lake
Fayetteville
10.0 out of 10, Exceptional, (13 reviews)
"Very convenient to shops and restaurants."
United States
Linda
$197 nightly
The price is $201
Nov 11 - Nov 12
Total with taxes and fees
Luxury Loft DWTN | Whiskey Trail + River + Lake
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.
$297 nightly
The price is $325
Nov 30 - Dec 1
Total with taxes and fees
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

Learn more about Winchester

Nestled between rolling hills, this charming town offers visitors the crystal-clear waters of Tims Ford Lake for boating and fishing. Explore downtown's historic courthouse square where local shops serve up Southern hospitality alongside the famous Winchester Swamp Festival each September.

See all hotels in Winchester
A calm lake with autumn foliage, a dock, and houses along the shore.

Top reviews in Winchester

Breakfast area
Best Western Inn

Best Western Inn

Best Western Inn
Winchester

10/10 Excellent

Karen at the front desk is why this rating gets 5 stars! I’ve stayed at hundreds of hotels, and never been greeted as kind and friendly and helpful as her! Thank you so much to her!!!
United States
Cindy
Reviewed October 18, 2021
Best Western Inn

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.

Explore a world of travel with Expedia