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Check prices for these dates

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

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
9.6 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
The price is AED 359
AED 687 total
includes taxes & fees
9 Nov - 10 Nov
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 AED 359
AED 657 total
includes taxes & fees
8 Nov - 9 Nov
Oasis on the Square
Living area

3. A quiet getaway.

A quiet getaway.
Winchester
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
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
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
The price is AED 277
AED 704 total
includes taxes & fees
8 Nov - 9 Nov
Newly Remodled Suite in Monteagle TN!
A hallway with wooden doors labeled 'The Cove' and 'The Overlook,' leading to a room with a view.

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.
The price is AED 255
AED 544 total
includes taxes & fees
24 Nov - 25 Nov
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.
The price is AED 595
AED 952 total
includes taxes & fees
4 Dec - 5 Dec
D-town w/ Balcony. Walk to Shops & Eats.
A room with a fireplace, a large statue, and a variety of decorative items.

9. 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, (54 reviews)
"The penthouse is a fantastical property, we enjoyed our stay very much."
United States
Jinny
The price is AED 511
AED 654 total
includes taxes & fees
8 Nov - 9 Nov
The Pythian Building Penthouse Apt. is centrally located on the city square.
A room with a brick wall, a bed with colorful pillows, a desk with a lamp, and a door.

10. “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.
The price is AED 689
AED 1,161 total
includes taxes & fees
8 Nov - 9 Nov
“Give My All for Tennessee” in Downtown Fayetteville Near Jack Daniels
A spacious room with a large wooden table, white chairs, and a brick wall.

11. 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
The price is AED 551
AED 912 total
includes taxes & fees
8 Nov - 9 Nov
Luxury Loft DWTN | Whiskey Trail + River + Lake
A modern apartment with a kitchenette, a dining area, a sofa, a bed, and a ceiling fan.

12. New Listing! Welcome to Bear Hollow Retreat!

New Listing! Welcome to Bear Hollow Retreat!
Monteagle
New Listing! Welcome to Bear Hollow Retreat!
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
The price is AED 277
AED 711 total
includes taxes & fees
24 Nov - 25 Nov
Adorable, Stylish Studio in Monteagle, TN!
A neatly made bed with white linens, two bedside tables with lamps, a wooden nightstand, and a coat rack.

14. Brand New, Adorable Suite Near the Caverns!

Brand New, Adorable Suite Near the Caverns!
Monteagle
Brand New, Adorable Suite Near the Caverns!
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 AED 662
AED 1,213 total
includes taxes & fees
30 Nov - 1 Dec
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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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.

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