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

Search Apartment Rentals 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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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, (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 $148
CA $287 total
includes taxes & fees
Oct 18 - Oct 19
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 CA $124
CA $258 total
includes taxes & fees
Oct 11 - Oct 12
Oasis on the Square
A bedroom with a bed, a nightstand, a lamp, a dresser, a wall art piece, and a rug.

3. 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
8.0 out of 10, Very good, (1 review)
"We were the third visitors in this brand new tiny house that is located in the backyard of the host’s home. The tiny house was well planned out and featured a main bedroom w/king-sized bed, well stocked fridge, & coffee bar and another separate room with toilet & shower. Area is very quiet & tranquil. Great location to rock on the front porch or take a stroll around the neighborhood."
United States
Mark
The price is CA $128
CA $177 total
includes taxes & fees
Oct 6 - Oct 7
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.

4. 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, (23 reviews)
"What a great property. Close to town and very clean and private. Would recommend to anyone that wants to stay in Lynchburg."
United States
Doug
The price is CA $192
CA $251 total
includes taxes & fees
Oct 13 - Oct 14
Lounges at Lynchburg Black House - within walking distance to Jack Daniels!
A wooden deck with outdoor seating and a covered area with large windows.

5. 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 CA $99
CA $277 total
includes taxes & fees
Oct 6 - Oct 7
Newly Remodled Suite in Monteagle TN!
A hallway with wooden doors labeled 'The Cove' and 'The Overlook,' leading to a room with a view.

6. Boutique Suite in Historic Tracy City!

Boutique Suite in Historic Tracy City!
Tracy City
10.0 out of 10, Exceptional, (5 reviews)
"Great stay, host was very accommodating. Would stay again! Clean accommodations, great location, and very comfortable."
United States
Eric S.
The price is CA $86
CA $198 total
includes taxes & fees
Oct 6 - Oct 7
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.

7. 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 CA $142
CA $270 total
includes taxes & fees
Nov 2 - Nov 3
D-town w/ Balcony. Walk to Shops & Eats.
A room with a fireplace, a large statue, and a variety of decorative items.

8. 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 $178
CA $242 total
includes taxes & fees
Oct 6 - Oct 7
The Pythian Building Penthouse Apt. is centrally located on the city square.
A rustic barn-style venue with wooden walls and a sloped ceiling, equipped with tables and chairs for dining or events.

9. New Listing! Welcome to Bear Hollow Retreat!

New Listing! Welcome to Bear Hollow Retreat!
Monteagle
The price is CA $99
CA $273 total
includes taxes & fees
Oct 6 - Oct 7
New Listing! Welcome to Bear Hollow Retreat!
A wooden deck with two Adirondack chairs and a table, a door with the number 6, and a view of greenery through the windows.

10. Adorable, Stylish Studio in Monteagle, TN!

Adorable, Stylish Studio in Monteagle, TN!
Monteagle
The price is CA $99
CA $277 total
includes taxes & fees
Oct 6 - Oct 7
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.

11. Brand New, Adorable Suite Near the Caverns!

Brand New, Adorable Suite Near the Caverns!
Monteagle
The price is CA $99
CA $277 total
includes taxes & fees
Oct 6 - Oct 7
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.

12. 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 $257
CA $494 total
includes taxes & fees
Oct 13 - Oct 14
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

Microtel Inn & Suites by Wyndham Manchester

Microtel Inn & Suites by Wyndham Manchester

10/10 Excellent
"Updated rooms and “pancake conveyer belt” at breakfast!"
Shanna 1-night trip
Posted 8 hours ago
Microtel Inn & Suites by Wyndham Manchester

Find out more about Winchester

Winchester Apartments information

Number of reviews
117
Accommodation
30 Apartments
Lowest Price
CA $177
Highest Price
CA $494

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