Search 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
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Winchester apartments

Fridge, microwave, oven, stovetop

Oasis on the Square

Oasis on the Square
Winchester
9.8 out of 10, Exceptional, (11 reviews)
"Great accommodations in downtown Winchester! "
United States
LeBron F.
The price is €143
includes taxes & fees
18 Jan - 19 Jan
Oasis on the Square
Interior

Winchester's Premier Downtown Loft!

Winchester's Premier Downtown Loft!
Winchester
9.8 out of 10, Exceptional, (11 reviews)
"We thoroughly enjoyed our stay in this comfortable and beautiful apartment, right in the heart of Winchester. It’s walkable to several restaurants and a great ice cream shop. Check-in and communication were smooth. "
United States
Jennifer M.
The price is €158
includes taxes & fees
15 Feb - 16 Feb
Winchester's Premier Downtown Loft!
Terrace/patio

Newly Remodled Suite in Monteagle TN!

Newly Remodled Suite in Monteagle TN!
Monteagle
9.2 out of 10, Wonderful, (9 reviews)
"We had a nicely refurbished room with a small kitchen in a quiet area. Would definitely stay again when we're back in the area."
United States
Carey D.
The price is €120
includes taxes & fees
19 Jan - 20 Jan
Newly Remodled Suite in Monteagle TN!
TV

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.
2.0 star property
Shelbyville
9.6 out of 10, Exceptional, (19 reviews)
"Wonderful stay. The apartment was perfect for our needs. Clean and conveniently located. The bed was comfy and we both slept great."
United States
Lucas B.
The price is €151
includes taxes & fees
19 Jan - 20 Jan
Centrally located in Shelbyville, just 1/4 mile from the Horse Show Grounds.
Smart TV

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

D-town w/ Balcony. Walk to Shops & Eats.
2.0 star property
Fayetteville
10.0 out of 10, Exceptional, (1 review)
" My stay at this loft with balcony was an extremely good experience, The host was very helpful answering questions and the amenities were superior!I would highly recommend this location to all."
United States
Donna R.
The price is €143
includes taxes & fees
18 Jan - 19 Jan
D-town w/ Balcony. Walk to Shops & Eats.
2 bedrooms, desk, iron/ironing board, travel cot

“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 €177
includes taxes & fees
18 Jan - 19 Jan
“Give My All for Tennessee” in Downtown Fayetteville Near Jack Daniels
Property grounds

Among the Laurels - New Tiny Home by The Caverns

Among the Laurels - New Tiny Home by The Caverns
2.0 star property
Monteagle
10.0 out of 10, Exceptional, (1 review)
"Really struggled to decide if I should share our experience as I worry this place will blow up & become impossible to book in the future! Absolutely great place, location is convenient yet off the beaten path. Owner’s communication was well above average, getting back to me within minutes of anything asked/sent. The attention to detail was next level, very cool/welcoming decor tied to the immediate area. So if you’re looking for an ok place to stay this isn’t the place for you, as it will well...
United States
Michael K.
The price is €261
includes taxes & fees
26 Jan - 27 Jan
Among the Laurels - New Tiny Home by The Caverns
Interior

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, (47 reviews)
"Very cool place to stay"
United States
ZBIGNIEW
The price is €164
includes taxes & fees
20 Jan - 21 Jan
The Pythian Building Penthouse Apt. is centrally located on the city square.
Fridge, microwave, oven, stovetop

Luxury Loft DWTN | Whiskey Trail + River + Lake

Luxury Loft DWTN | Whiskey Trail + River + Lake
Fayetteville
9.8 out of 10, Exceptional, (6 reviews)
"Great place to stay, newly renovated with high end appliances."
United States
Thomas C.
The price is €264
includes taxes & fees
15 Feb - 16 Feb
Luxury Loft DWTN | Whiskey Trail + River + Lake
Living area

Boutique Sweet in Historic Tracy City!

Boutique Sweet in Historic Tracy City!
2.0 star property
Tracy City
The price is €94
includes taxes & fees
17 Jan - 18 Jan
Boutique Sweet in Historic Tracy City!
Interior

Downtown View. Walk to Shops & Eats.

Downtown View. Walk to Shops & Eats.
2.0 star property
Fayetteville
The price is €153
includes taxes & fees
18 Jan - 19 Jan
Downtown View. Walk to Shops & Eats.
Interior

Sleeps 6. Two Downtown Lofts Combined.

Sleeps 6. Two Downtown Lofts Combined.
2.0 star property
Fayetteville
The price is €262
includes taxes & fees
18 Jan - 19 Jan
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

Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak

Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak

10/10 Excellent
"Beautiful home and location. Hosts are great!"
Barbara K. 3-night trip
Posted 2 days ago
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak

Find out more about Winchester

Winchester Apartments information

Number of reviews
103
Accommodation
30 Apartments
Lowest Price
€120
Highest Price
€264

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?
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: Free WiFi, a balcony and a fireplace are included . On-site laundry facilities and a games room are on site . Winchester's Premier Downtown Loft!: Includes a fireplace and a dining area . Access to on-site laundry facilities is available on site . Dry Jack Tim- Water Views, Pool, Outdoor Fireplace: Includes free WiFi and a fireplace . Access to on-site laundry facilities is available 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 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, 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.