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Compare 16 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 AED 629
AED 1,153 total
includes taxes & fees
23 Feb - 24 Feb
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, (2)
"The exterior of this charming little spot gives me "OK Corral." It's like I traveled "out west" to find gold. It's a perfect spot for family events too. There's nice event hall as part of the building. I picture a family booking several rooms for a wedding or anniversary party. The room I stayed in was perfect! I had all I needed to feel comfy including little kitchenette which allowed me to cook my meals. The inside is where the old meets new. "
The price is AED 177
AED 476 total
includes taxes & fees
24 Feb - 25 Feb
Newly Remodled Suite in Monteagle TN!

Oasis on the Square

10.0 out of 10, Exceptional, (1)
"We spent three nights in this awesome apartment. It was perfectly located and had everything we needed. The inside was very well done and the owner was very communicative. I would definitely stay here again. Maybe next time it won’t be 10 degrees and we can explore the downtown a little more"
The price is AED 261
AED 596 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
9.2 out of 10, Wonderful, (9)
"Great location. Cute place. Very clean apartment and safe neighborhood! We enjoyed our stay and would definitely stay at this property again if we are back in town. "
The price is AED 400
AED 712 total
includes taxes & fees
24 Feb - 25 Feb
Centrally located in Shelbyville, just 1/4 mile from the Horse Show Grounds.

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

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 AED 511
AED 684 total
includes taxes & fees
23 Feb - 24 Feb
The Pythian Building Penthouse Apt. is centrally located on the city square.

Winchester's Premier Downtown Loft!

9.4 out of 10, Exceptional, (3)
"Went to visit TN Whiskey Trail. We determined Winchester, TN would be a good spot to stage from. This loft was ideal...right in the middle of Winchester and esay walking to numerous restaurants in a quaint little town. Adam was a great host and was always Johnny on the spot. Due to impending Artic Blast, he provided two addtional space heaters to keep the loft warm.We will be back! Thank you, Adam."
The price is AED 261
AED 596 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

Hook, Wine, Sinker Unit B

Hook, Wine, Sinker Unit B

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

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 715 total
includes taxes & fees
23 Feb - 24 Feb
“Give My All for Tennessee” in Downtown Fayetteville Near Jack Daniels
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

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

"The Hawk Nest" cabin on Tims Ford Lake

9.0 out of 10, Wonderful, (10)
"This is a clean, comfortable and well-appointed cabin and a well-maintained property. It was perfectly simple and had everything we needed…even a flashlight, which we forgot. Our host generously accommodated our special request. Access to water with a kayak was easy. We would love to rent this again! Leslie November 2024"
The price is AED 364
AED 1,072 total
includes taxes & fees
1 Mar - 2 Mar
"The Hawk Nest" cabin on Tims Ford Lake

Lakeside Haven w/Dock/Slip, Fire Pit, Game Room, Kayaks,

10.0 out of 10, Exceptional, (5)
"A get together for high school friends after many years and we all turned 60. "
Lakeside Haven w/Dock/Slip, Fire Pit, Game Room, Kayaks,
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 5 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. Hook, Wine, Sinker Unit B: Amenities include free WiFi. Access to a game room is available on site.
How many apartments can I expect to find in Winchester?
Expedia has 5 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 State Park and Tims Ford are a couple of great spots to enjoy the outdoors. While here, Tims Ford Lake 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.