A calm lake with autumn foliage, a dock, and houses along the shore.

Search and Rent Winchester Condos

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7
No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

A hotel room with a bed, a chair, a small table, a desk, and a mirror.

1. Best Western Inn

Best Western Inn
2.5 star property
Winchester
8.8 out of 10, Excellent, (756 reviews)
"Our room was very nice and staff were great."
United States
kenneth
$101 nightly
The price is $116
Oct 20 - Oct 21
Total with taxes and fees
Best Western Inn
A modern living room with a built-in aquarium, a leather sofa, and a patterned rug.

2. Winchester's Premier Downtown Loft!

Winchester's Premier Downtown Loft!
Winchester
9.6 out of 10, Exceptional, (18 reviews)
"It was wonderful and right in the center of downtown winchester. Very clean and beautiful loft and amazing lighting to have long night talks. Truly amazing"
United States
Gianmarco
$179 nightly
The price is $194
Oct 15 - Oct 16
Total with taxes and fees
Winchester's Premier Downtown Loft!
A modern kitchen with dark cabinetry, stainless steel appliances, and a light-colored backsplash.

3. Oasis on the Square

Oasis on the Square
Winchester
9.8 out of 10, Exceptional, (13 reviews)
"Great location on the square with plenty of dining options a short walk away."
United States
possible Amanda H
$173 nightly
The price is $187
Oct 18 - Oct 19
Total with taxes and fees
Oasis on the Square
A lakeside view with a wooden dock, a grassy area with a gazebo, and a building with multiple windows in the background.

4. Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family

Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Winchester
10.0 out of 10, Exceptional, (39 reviews)
"Great property!"
United States
Greg B.
$279 nightly
The price is $319
Oct 31 - Nov 1
Total with taxes and fees
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
A spacious kitchen with granite countertops, white cabinetry, and a built-in dishwasher. There are multiple windows providing natural light and a view of the outdoors.

5. Tiny Home w/ RV Hookups

Tiny Home w/ RV Hookups
Winchester
9.0 out of 10, Wonderful, (11 reviews)
"Great place to stay! "
United States
Erica P.
$173 nightly
The price is $198
Oct 19 - Oct 20
Total with taxes and fees
Tiny Home w/ RV Hookups
A stainless steel outdoor grill with four burners, a chimney, and a control panel, set against a wooden fence and surrounded by trees.

6. *NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub

*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
Winchester
$521 nightly
The price is $539
Oct 25 - Oct 26
Total with taxes and fees
*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
A marina with boats docked, a dock with a covered area, and a sunset over water.

7. Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home

Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
3.0 star property
Winchester
$864 nightly
The price is $987
Oct 19 - Oct 20
Total with taxes and fees
Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
A white RV with 'Campbound' branding parked by a lake with picnic tables and chairs.

8. Stationary tiny camper in Winchester, TN with pond and mountain views.

Stationary tiny camper in Winchester, TN with pond and mountain views.
Winchester
10.0 out of 10, Exceptional, (1 review)
"I definitely give this property 5 gold stars in all categories. It was EXACTLY as advertised with the owner taking care to provide little 'extras' on top of that in the form of snacks, coffee, etc... The electric awning is not even mentioned, but it makes a nice outside sitting area with the provided picnic table. The tiny camper is perfect for a night or a few for 1-2 people. Very clean, great communication and all the things you would want."
United States
Jr H.
$160 nightly
The price is $182
Oct 20 - Oct 21
Total with taxes and fees
Stationary tiny camper in Winchester, TN with pond and mountain views.
A log cabin with a porch, outdoor seating, and a welcome sign.

9. "The Hawk Nest" cabin on Tims Ford Lake

"The Hawk Nest" cabin on Tims Ford Lake
Winchester
9.4 out of 10, Exceptional, (26 reviews)
"Super nice, peaceful get-away. Love the private dock and all the sitting areas outside. Feels secluded and I like it. Very easy access as well."
United States
Andrew N.
$372 nightly
The price is $425
Oct 14 - Oct 15
Total with taxes and fees
"The Hawk Nest" cabin on Tims Ford Lake
Living area

10. A quiet getaway.

A quiet getaway.
Winchester
$341 nightly
The price is $390
Oct 14 - Oct 15
Total with taxes and fees
A quiet getaway.
A wooden deck with a picnic table and chairs, surrounded by windows and a railing.

11. Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub

Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
Winchester
10.0 out of 10, Exceptional, (83 reviews)
"We had a great time! "
United States
Cindy O.
$857 nightly
The price is $979
Nov 1 - Nov 2
Total with taxes and fees
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
A spacious living room with a large flat-screen TV, comfortable seating, a dining area, and a staircase leading to an upper level.

12. Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12

Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
Winchester
10.0 out of 10, Exceptional, (27 reviews)
"This property conbined with the unit nexf door worked perfectly for our group of 18 people to enjoy a great 4th of july week at the lake."
United States
Timothy W.
$685 nightly
The price is $782
Oct 18 - Oct 19
Total with taxes and fees
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
A spacious living room with a stone fireplace, comfortable seating, a flat-screen TV, and large windows offering natural light.

13. Quality Inn Decherd - Winchester

Quality Inn Decherd - Winchester
2.5 star property
Decherd
7.0 out of 10, Good, (316 reviews)
"Good"
United States
Valerie
$76 nightly
The price is $91
Nov 12 - Nov 13
Total with taxes and fees
Quality Inn Decherd - Winchester
A hotel with a brick facade, a covered entrance, and a parking lot.

14. Holiday Inn Express Hotel & Suites Tullahoma by IHG

Holiday Inn Express Hotel & Suites Tullahoma by IHG
2.5 star property
Tullahoma
9.0 out of 10, Wonderful, (722 reviews)
$92 nightly
The price is $108
Nov 13 - Nov 14
Total with taxes and fees
Holiday Inn Express Hotel & Suites Tullahoma by IHG
A red mailbox with "McCormick Farmall" on it, a black barbecue grill, a red metal table and chairs, and a sign that says "Come In We're Open".

15. A very rustic converted pole barn unique cozy cabin

A very rustic converted pole barn unique cozy cabin
Estill Springs
9.8 out of 10, Exceptional, (167 reviews)
"This was a perfect stay for us while we were visiting family! We look forward to staying again when we’re in the area."
United States
Jacquelyne S.
$145 nightly
The price is $165
Oct 15 - Oct 16
Total with taxes and fees
A very rustic converted pole barn unique cozy cabin
A spacious room with a stone fireplace, a flat-screen TV mounted above it, and a green upholstered sofa.

16. Quality Inn Monteagle

Quality Inn Monteagle
2.5 star property
Downtown Monteagle
8.8 out of 10, Excellent, (965 reviews)
"Room was very clean. Staff was especially nice and welcoming!"
United States
Gloria
$80 nightly
The price is $95
Nov 1 - Nov 2
Total with taxes and fees
Quality Inn Monteagle
A lodge with a large wooden overhang, stone pillars, and a stone entrance.

17. The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins
3.0 star property
Monteagle
8.4 out of 10, Very good, (1,301 reviews)
"Lovely property set in extensive grounds. Extremely pet friendly and a comfortable, relaxing place to stay!"
United States
Theodosios
$56 nightly
The price is $64
Oct 19 - Oct 20
Total with taxes and fees
The Smokehouse Lodge and Cabins
A living room with a leather sofa, a coffee table, a bookshelf, and a large plant.

18. Grand Lux Inn

Grand Lux Inn
3.0 star property
Tullahoma
9.8 out of 10, Exceptional, (281 reviews)
"Obsessed with this place!"
United States
Lana
$103 nightly
The price is $120
Oct 14 - Oct 15
Total with taxes and fees
Grand Lux Inn
A modern hotel building with a sign reading "LivSmart Studios by Hilton".

19. LivSmart Studios by Hilton Tullahoma

LivSmart Studios by Hilton Tullahoma
2.5 star property
Tullahoma
9.6 out of 10, Exceptional, (71 reviews)
"Incredibly clean and very quiet. Looks and smells brand new and was very nice. Will absolutely stay here again when I'm in town"
United States
Jeff
$110 nightly
The price is $129
Oct 22 - Oct 23
Total with taxes and fees
LivSmart Studios by Hilton Tullahoma
A modern reception area with a herringbone-patterned carpet, two reception desks, and a wooden partition with a grid design.

20. La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB

La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB
3.0 star property
Manchester
9.0 out of 10, Wonderful, (529 reviews)
"Super clean and nice - nicest La Quinta I have stayed at"
United States
Timothy
$107 nightly
The price is $127
Oct 25 - Oct 26
Total with taxes and fees
La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB
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

The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

8/10 Good
"Handy access........................."
Gregory 1-night trip
Posted 6 hours ago
The Smokehouse Lodge and Cabins

Find out more about Winchester

Winchester Condo Rentals information

Number of reviews
3,567
Accommodation
1 Condo Rentals
Lowest Price
$64
Highest Price
$987

Explore a world of travel with Expedia