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Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 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, (12 reviews)
"Great love the location "
United States
Zita L.
The price is AED 296
AED 636 total
includes taxes & fees
8 Feb - 9 Feb
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 AED 334
AED 679 total
includes taxes & fees
9 Feb - 10 Feb
Winchester's Premier Downtown Loft!
Smart TV

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

D-town w/ Balcony. Walk to Shops & Eats.
Fayetteville
10.0 out of 10, Exceptional, (3 reviews)
" 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 AED 313
AED 619 total
includes taxes & fees
7 Feb - 8 Feb
D-town w/ Balcony. Walk to Shops & Eats.
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 AED 197
AED 496 total
includes taxes & fees
8 Feb - 9 Feb
Newly Remodled Suite in Monteagle TN!
2 bedrooms, desk, iron/ironing board, travel crib

“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 AED 551
AED 743 total
includes taxes & fees
7 Feb - 8 Feb
“Give My All for Tennessee” in Downtown Fayetteville Near Jack Daniels
Fridge, microwave, oven, stovetop

Comfort Time after time in Fayetteville Tennessee. 3-bedroom pet friendly apt.

Comfort Time after time in Fayetteville Tennessee. 3-bedroom pet friendly apt.
Fayetteville
10.0 out of 10, Exceptional, (5 reviews)
"What a terrific stay!! As soon as you walk in, this home is welcoming and comfortable. Extremely clean and convenient to any and all your needs. Definitely will highly recommend!! "
United States
Jeremy S.
The price is AED 430
AED 566 total
includes taxes & fees
7 Feb - 8 Feb
Comfort Time after time in Fayetteville Tennessee. 3-bedroom pet friendly apt.
Property grounds

Among the Laurels - New Tiny Home by The Caverns

Among the Laurels - New Tiny Home by The Caverns
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 AED 441
AED 1,088 total
includes taxes & fees
7 Feb - 8 Feb
Among the Laurels - New Tiny Home by The Caverns
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 AED 353
AED 714 total
includes taxes & fees
9 Feb - 10 Feb
Luxury Loft DWTN | Whiskey Trail + River + Lake
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.
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 AED 364
AED 670 total
includes taxes & fees
7 Mar - 8 Mar
Centrally located in Shelbyville, just 1/4 mile from the Horse Show Grounds.
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 AED 511
AED 684 total
includes taxes & fees
8 Feb - 9 Feb
The Pythian Building Penthouse Apt. is centrally located on the city square.
Smart TV, video games

Cozy 2-bedroom apartment in charming downtown South Pittsburg, TN

Cozy 2-bedroom apartment in charming downtown South Pittsburg, TN
South Pittsburg
The price is AED 294
AED 516 total
includes taxes & fees
27 Feb - 28 Feb
Cozy 2-bedroom apartment in charming downtown South Pittsburg, TN
1 bedroom, desk, free WiFi, bed sheets

Guest Suite in Cowan with private entrance: 10 min to University of the South

Guest Suite in Cowan with private entrance: 10 min to University of the South
Cowan
The price is AED 441
AED 586 total
includes taxes & fees
7 Feb - 8 Feb
Guest Suite in Cowan with private entrance: 10 min to University of the South
Living area

Boutique Suite in Historic Tracy City!

Boutique Suite in Historic Tracy City!
Tracy City
The price is AED 147
AED 367 total
includes taxes & fees
7 Feb - 8 Feb
Boutique Suite in Historic Tracy City!
Interior

Sleeps 6. Two Downtown Lofts Combined.

Sleeps 6. Two Downtown Lofts Combined.
Fayetteville
The price is AED 595
AED 1,179 total
includes taxes & fees
16 Feb - 17 Feb
Sleeps 6. Two Downtown Lofts Combined.
Interior

Downtown View. Walk to Shops & Eats.

Downtown View. Walk to Shops & Eats.
Fayetteville
The price is AED 313
AED 619 total
includes taxes & fees
9 Feb - 10 Feb
Downtown View. Walk to Shops & Eats.
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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Top Winchester Hotel Reviews

Quality Inn Monteagle

Quality Inn Monteagle

10/10 Excellent
"Good value. Will stay again. "
Jennifer 1-night trip
Posted 2 days ago
Quality Inn Monteagle

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?
Winchester's Premier Downtown Loft!: Includes fireplaces and separate dining areas. Access to onsite laundry facilities is available on site. Dry Jack Tim- Water Views, Pool, Outdoor Fireplace: Includes free WiFi and fireplaces. Access to onsite laundry facilities is available 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. 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.
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 Hammers and Twin Creeks Marina, whereas Tims Ford and Tims Ford Lake are a couple of great spots to enjoy the outdoors. While here, Tim's Ford Marina and Tims Ford State Park 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.