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Compare 17 Apartments in Winchester with updated reviews, rates, and availability.

Newly Remodled Suite in Monteagle TN!

10.0 out of 10, Exceptional, (5)
"Very cozy and clean. Bed and couch were both very comfortable. Kitchen was also an added bonus. Nice rocking chairs and table outside of the room to enjoy nature and fresh mountain air. Will definitely come back again. Host were very awesome also ."
The price is AED 165
AED 464 total
includes taxes & fees
5 May - 6 May
Newly Remodled Suite in Monteagle TN!

Winchester's Premier Downtown Loft!

9.4 out of 10, Exceptional, (6)
"This was my first Vrbo and I couldn’t have had a better experience. The loft was very clean and welcoming. Our host was great with communicating with us all the information to make our stay great. "
The price is AED 290
AED 629 total
includes taxes & fees
5 May - 6 May
Winchester's Premier Downtown Loft!

Oasis on the Square

10.0 out of 10, Exceptional, (4)
"Great accommodations in downtown Winchester! "
The price is AED 290
AED 629 total
includes taxes & fees
4 May - 5 May
Oasis on the Square

2BD/2BA Luxury Loft on Historic Fayetteville Square

9.0 out of 10, Wonderful, (2)
"Beautiful loft in downtown. Central location for travel needs. Cat was fabulous and responsive. Thanks for a great stay. "
The price is AED 629
AED 1,147 total
includes taxes & fees
12 May - 13 May
2BD/2BA Luxury Loft on Historic Fayetteville Square

Lakeside Tiny Home in The Retreat by Water's Edge

10.0 out of 10, Exceptional, (17)
"Just what we needed. Local fishing, beautiful scenery, very nice accomendations. Will definitely go back again."
Lakeside Tiny Home in The Retreat by Water's Edge

Fireside Apartment

9.8 out of 10, Exceptional, (39)
"Perfect spot to stay!"
Fireside Apartment

“Give My All for Tennessee” in Downtown Fayetteville Near Jack Daniels

10.0 out of 10, Exceptional, (1)
"This place was super fun and adorable. Loads of thoughtful touches (lots of TN themed decor, local snacks, nice toiletries). Plenty of things are within walking distance. It was perfect for our weekend visit. The host was super responsive to all requests. "
The price is AED 528
AED 712 total
includes taxes & fees
4 May - 5 May
“Give My All for Tennessee” in Downtown Fayetteville Near Jack Daniels

Centrally located in Shelbyville, just 1/4 mile from the Horse Show Grounds.

2.0 star property
9.2 out of 10, Wonderful, (10)
"The property was just as described. It had a nice comfortable bed, great location, and was very clean. "
The price is AED 400
AED 712 total
includes taxes & fees
4 May - 5 May
Centrally located in Shelbyville, just 1/4 mile from the Horse Show Grounds.

Carriage House;Caverns;Fiery Gizzard;Pets;S. Cumberland Parks;Bluff; Longhorns

10.0 out of 10, Exceptional, (150)
"Beautiful area with great hosts"
Carriage House;Caverns;Fiery Gizzard;Pets;S. Cumberland Parks;Bluff; Longhorns

The Pythian Building Penthouse Apt. is centrally located on the city square.

10.0 out of 10, Exceptional, (34)
"This place was amazing!!!!"
The price is AED 511
AED 684 total
includes taxes & fees
7 May - 8 May
The Pythian Building Penthouse Apt. is centrally located on the city square.

Beautiful cottage, close to rivers, creeks, lakes for fishing, boating, hunting

10.0 out of 10, Exceptional, (19)
"Cabin and owners where wonderful. We traveled with our small little dog and they had a little area fenced in area for the dog which was very handy. The cabin was clean and had everything we needed during our stay. 5 star all the way"
Beautiful cottage, close to rivers, creeks, lakes for fishing, boating, hunting

3 Bedroom Cozy Home Minutes from Tims Ford Lake

9.0 out of 10, Wonderful, (4)
"Property as described and quiet. Nice neighborhood and easy to find. Close to everything."
3 Bedroom Cozy Home Minutes from Tims Ford Lake

Beautifully Renovated Studio 2 miles from the Marina

10.0 out of 10, Exceptional, (13)
"The place was exactly as pictured with an easy check-in and out process. Was a perfect little place for us to stay for a long weekend!"
The price is AED 275
AED 708 total
includes taxes & fees
4 May - 5 May
Beautifully Renovated Studio 2 miles from the Marina

Renovated Cozy Home Minutes from Tims Ford Lake

4.0 out of 10, (2)
"This property was well located for our business trip. The picture of the property shown on the listing is a somewhat deceptive, the actual entrance to the rental can't be seen. The inside was clean and supplied for our visit. Wash cloths, hand towels and toilet paper were in short supply for our 4 day visit. Outside the grounds were somewhat cluttered and the picnic table had a broken seat. A leaking toilet valve and loose kitchen faucet will need attention."
The price is AED 184
AED 633 total
includes taxes & fees
6 May - 7 May
Renovated Cozy Home Minutes from Tims Ford Lake

Spacious Historic 3-bedroom apartment with AC, WiFi in charming Winchester

Spacious Historic 3-bedroom apartment with AC, WiFi in charming Winchester

Hook, Wine, Sinker Unit B

Hook, Wine, Sinker Unit B

Brand New Studio with a Bluff View

Brand New Studio with a Bluff View
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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Other property types in Winchester

Million Dollar Views: Lakefront, Dock, Kayaks+More

10.0 out of 10, Exceptional, (44)
"The house is clean, updated and the views are amazing! We were there in January, so we didn't use the dock, but the house was perfect. The living space and kitchen is large and open, the bedrooms are spacious, and the movie screen set up downstairs was perfect to watch a game and a movie. Will be back!"
Million Dollar Views: Lakefront, Dock, Kayaks+More

Sunset Cove- Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc

9.8 out of 10, Exceptional, (18)
"Great location. Very clean, well equipped, good communication with managers."
Sunset Cove- Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc

Dock, Water Views, Kayaks, Fire Pit, Game Room

10.0 out of 10, Exceptional, (15)
"Beautiful home with everything we needed for our stay! The kids loved the game/bunk room and golf cart rides to the awesome dock. We enjoyed it so much and felt right at home!"
Dock, Water Views, Kayaks, Fire Pit, Game Room
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.

Frequently asked questions

What's it like to stay at an apartment in Winchester?
You’ll find 6 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?
Winchester’s Premier Downtown Loft!: Includes fireplaces and separate dining areas. Access to onsite laundry facilities is available on site. Beautifully Renovated Studio 2 miles from the Marina: Free WiFi and Smart TVs are included. Access to onsite laundry facilities is available on site. Spacious Historic 3-bedroom apartment with AC, WiFi in charming Winchester: Amenities include Smart TVs. Access to onsite laundry facilities is available on site.
How many apartments can I expect to find in Winchester?
Expedia has 6 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.