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

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

10.0 out of 10, Exceptional, (149)
"What a beautiful, peaceful farm setting! We came for a concert at the Caverns, but really loved your property, dogs and guineas! Thanks for your hospitality"
Carriage House;Caverns;Fiery Gizzard;Pets;S. Cumberland Parks;Bluff; Longhorns

2BD/2BA Luxury Loft on Historic Fayetteville Square

9.0 out of 10, Wonderful, (2)
"Everything was great except music from The Elk Taproom below us. Even though it ended at 10 p.m.It still was annoying trying to wind down and watch tv."
The price is SAR 643
SAR 1,192 total
includes taxes & fees
26 Jan - 27 Jan
2BD/2BA Luxury Loft on Historic Fayetteville Square

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

10.0 out of 10, Exceptional, (18)
"Very quaint and quiet location. It perfectly suited our needs. Loved waking up to baby cows just across the road. Lots of hot water for a long shower if needed. It was close to our friends home and a small ride to Chattanooga. "
Beautiful cottage, close to rivers, creeks, lakes for fishing, boating, hunting

Newly Remodled Suite in Monteagle TN!

10.0 out of 10, Exceptional, (1)
"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 SAR 181
SAR 503 total
includes taxes & fees
26 Jan - 27 Jan
Newly Remodled Suite in Monteagle TN!

Oasis on the Square

The price is SAR 296
SAR 643 total
includes taxes & fees
23 Feb - 24 Feb
Oasis on the Square

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

2.0 star property
9.0 out of 10, Wonderful, (8)
"Very impressed with the condo, it was stocked with everything you need in the kitchen, bathroom and the bedrooms. The bed was a bit uncomfortable but not a deal killer. "
The price is SAR 409
SAR 728 total
includes taxes & fees
27 Jan - 28 Jan
Centrally located in Shelbyville, just 1/4 mile from the Horse Show Grounds.

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

10.0 out of 10, Exceptional, (30)
"We loved our overnight stay! It was to have time alone together and there was so many unique items and conversation pieces in the room it kept us occupied/talking for hours. Allowed us to leave work behind and enjoy our time. The owner is super as well!"
The price is SAR 521
SAR 698 total
includes taxes & fees
23 Feb - 24 Feb
The Pythian Building Penthouse Apt. is centrally located on the city square.

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."
Renovated Cozy Home Minutes from Tims Ford Lake

Beautifully Renovated Studio 2 miles from the Marina

10.0 out of 10, Exceptional, (12)
"Had an issue with the television, but it was rectified fairly quickly."
The price is SAR 263
SAR 694 total
includes taxes & fees
25 Jan - 26 Jan
Beautifully Renovated Studio 2 miles from the Marina

Lakeside Tiny Home in The Retreat by Water's Edge

10.0 out of 10, Exceptional, (14)
"I loved my stay! Very clean and comfortable. There were a few ants in the kitchen but it didn't bother me much and had been treated by pest control. Location right by the lake was perfect. The whole community was quite lovely and inviting. My little issue was the lack of kitchen knives for cutting fruits and veggies. There were a couple tiny knives and a bread knife, but nothing like a chef's knife. No peeler either. Maybe I just missed it?? I made due but those seem like regular kitchen items...
Lakeside Tiny Home in The Retreat by Water's Edge

3 Bedroom Cozy Home Minutes from Tims Ford Lake

9.0 out of 10, Wonderful, (4)
"This is a really cute house. The pictures were true to the property. Paul was very quick to respond to emails. He continually works to make this place perfect for his guests. It is conveniently located near grocer stores, restaurants, and the lake."
The price is SAR 225
SAR 779 total
includes taxes & fees
10 Feb - 11 Feb
3 Bedroom Cozy Home Minutes from Tims Ford Lake

Winchester's Premier Downtown Loft!

9.0 out of 10, Wonderful, (2)
"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 SAR 296
SAR 643 total
includes taxes & fees
23 Feb - 24 Feb
Winchester's Premier Downtown Loft!

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

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

Brand New Studio with a Bluff View

Brand New Studio with a Bluff View

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

The price is SAR 539
SAR 730 total
includes taxes & fees
26 Jan - 27 Jan
“Give My All for Tennessee” in Downtown Fayetteville Near Jack Daniels

Hook, Wine, Sinker Unit B

Hook, Wine, Sinker Unit B
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, (39)
"We have been traveling for weekend trips with our friends for years and this was the best house yet. Beautiful lake views, clean house, well stocked, and room for everyone. We had the best time! "
Million Dollar Views: Lakefront, Dock, Kayaks+More

Family friendly lake front home with private dock in a cove

10.0 out of 10, Exceptional, (22)
"Nice location, easy instructions in the binder to reference information about the stay. Prior guests left some lovely floats by the dock. Friendly neighbors as well."
Family friendly lake front home with private dock in a cove

Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK

10.0 out of 10, Exceptional, (23)
"We enjoyed spending special family time. The kitchen is perfect for a multi family gathering. Liked having multiple spaces to eat, play games, a do crafts. Having the kayaks (adult and kid size) was wonderful. Realized we were one kayak short late in the week and could have used all that were stated in the description. The kids loved fishing off the dock! Having kids fishing poles was a huge hit! We had to borrow another little kid life jacket from a friend. We rented a boat for the day and the...
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK
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?
Beautifully Renovated Studio 2 miles from the Marina: Free WiFi and Smart TVs are included. Winchester’s Premier Downtown Loft!: Fireplaces and separate dining areas are included. Hook, Wine, Sinker Unit B: Includes free WiFi. Access to a game room 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 Tim’s Ford Marina and Hammers, whereas Tims Ford State Park and Tims Ford are a couple of great spots to enjoy the outdoors. While here, Twin Creeks Marina and Tims Ford Lake 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.