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

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Winchester vacation homes

A modern living room with a blue sofa, a staircase, a kitchen, and a fireplace.

1. Iconic Winchester home near Tims Ford State Park!

Iconic Winchester home near Tims Ford State Park!
Winchester
The price is ￥11,533
￥64,798 total
includes taxes & fees
Oct 29 - Oct 30
Iconic Winchester home near Tims Ford State Park!
A lakeside view with a wooden dock, a grassy area with a gazebo, and a building with multiple windows in the background.

2. 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, (40 reviews)
"Great property!"
United States
Greg B.
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
A kitchen with a coffee machine, a sink, and a window with curtains.

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

*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
Winchester
10.0 out of 10, Exceptional, (1 review)
"This was the perfect place for our family of five to use while visiting University of the South!! We weren’t able to take advantage of the hot tub or kayaks but we did wander the property and take advantage of the beautiful water views.Make sure to visit the Sunrise Cafe while you are there! Order a plate of cinnamon role pancakes for the table!! Delicious."
United States
Vonda R.
The price is ￥18,485
￥81,899 total
includes taxes & fees
Nov 1 - Nov 2
*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

4. 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
The price is ￥48,022
￥161,723 total
includes taxes & fees
Oct 29 - Oct 30
Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
Dining

5. The Lakeside Getaway

The Lakeside Getaway
Winchester
9.8 out of 10, Exceptional, (6 reviews)
"Incredible "
United States
Jim C.
The price is ￥23,309
￥89,271 total
includes taxes & fees
Nov 10 - Nov 11
The Lakeside Getaway
A wooden deck with a picnic table and chairs, surrounded by windows and a railing.

6. 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.
The price is ￥63,783
￥143,561 total
includes taxes & fees
Nov 2 - Nov 3
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.

7. 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.
The price is ￥55,122
￥123,211 total
includes taxes & fees
Nov 2 - Nov 3
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
A modern living room with a TV, wooden flooring, and a large window offering a view of greenery.

8. Treetop Mountain Retreat Near Sewanee | Sleeps 6

Treetop Mountain Retreat Near Sewanee | Sleeps 6
Sewanee
10.0 out of 10, Exceptional, (2 reviews)
"Great proximity to the college with ample parking."
United States
Lisa C.
The price is ￥17,853
￥72,458 total
includes taxes & fees
Oct 29 - Oct 30
Treetop Mountain Retreat Near Sewanee | Sleeps 6
A modern dining area with a wooden table, bar stools, a TV, and a fireplace.

9. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (26 reviews)
"Great place to stay. Had everything we needed. Great location."
United States
Jennifer T.
The price is ￥12,402
￥32,476 total
includes taxes & fees
Oct 29 - Oct 30
Whiskey Trails Cottage
A modern kitchen with grey cabinets, a central island with a red flower arrangement, and a "FAMILY" sign above the sink.

10. Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!

Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
Pelham
9.6 out of 10, Exceptional, (39 reviews)
"House is kept in great condition, beautiful location, and perfect stay when attending the caverns (12 minutes away)"
United States
Antonio M.
The price is ￥11,024
￥41,297 total
includes taxes & fees
Nov 2 - Nov 3
Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
A dining area with a round table and four chairs, a kitchen in the background, and a blue patterned rug.

11. Spacious private guesthouse within minutes of Tims Ford Lake and Woods Reservoir

Spacious private guesthouse within minutes of Tims Ford Lake and Woods Reservoir
Tullahoma
9.6 out of 10, Exceptional, (8 reviews)
"Very clean and convenient. The host was was very helpful."
United States
George G.
The price is ￥23,624
￥30,613 total
includes taxes & fees
Nov 21 - Nov 22
Spacious private guesthouse within minutes of Tims Ford Lake and Woods Reservoir
A cozy living area with a fireplace, a sofa, a dining table, and a kitchen with brick walls.

12. Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns

Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
Pelham
10.0 out of 10, Exceptional, (17 reviews)
"This is going to be my go to spot for all Caverns shows. Comfy, spacious and perfect for my crew of 4. The cafe attached was a nice bonus!"
United States
Andrea
The price is ￥10,237
￥30,297 total
includes taxes & fees
Nov 2 - Nov 3
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
A spacious living room with a grey sofa, a round wicker chair, and large windows offering a view of trees.

13. Lake Life 4 Bedroom, 3 Bath, Sleeps 12.

Lake Life 4 Bedroom, 3 Bath, Sleeps 12.
Estill Springs
9.8 out of 10, Exceptional, (35 reviews)
"Great house and even better location! Will be staying again!!"
United States
Courtney C.
The price is ￥60,431
￥129,281 total
includes taxes & fees
Oct 29 - Oct 30
Lake Life 4 Bedroom, 3 Bath, Sleeps 12.
A white house with a covered porch, stone pathway, and outdoor seating.

14. Forest Retreat: Poolside Bliss Close to Campus

Forest Retreat: Poolside Bliss Close to Campus
Sewanee
10.0 out of 10, Exceptional, (13 reviews)
"Lovely home in a great location"
United States
Denise M.
The price is ￥26,211
￥85,283 total
includes taxes & fees
Nov 1 - Nov 2
Forest Retreat: Poolside Bliss Close to Campus
A cozy living room with a fireplace, wooden flooring, a sofa, and a sliding glass door leading to an outdoor area.

15. Cove Sweet Cove - 3BR + 2BR Near the Caverns!

Cove Sweet Cove - 3BR + 2BR Near the Caverns!
Pelham
10.0 out of 10, Exceptional, (13 reviews)
"The cabin was just as advertised. It was clean and perfect location for the concert at the cavern. I would book again."
United States
Joanne G.
The price is ￥10,237
￥38,620 total
includes taxes & fees
Nov 2 - Nov 3
Cove Sweet Cove - 3BR + 2BR Near the Caverns!
A cozy interior space with a sliding glass door leading to an outdoor deck.

16. Holiday House

Holiday House
Tullahoma
9.6 out of 10, Exceptional, (14 reviews)
"Family friendly"
United States
Trinette N.
The price is ￥43,310
￥91,995 total
includes taxes & fees
Oct 29 - Oct 30
Holiday House
A cozy living room with a sofa, armchair, and ottoman, wooden walls, and large windows with curtains.

17. On the University of the South campus, Sewanee, TN.

On the University of the South campus, Sewanee, TN.
Sewanee
9.8 out of 10, Exceptional, (36 reviews)
"wonderful place to stay right on Sewanee's campus!"
United States
katherine v.
The price is ￥48,203
￥93,856 total
includes taxes & fees
Nov 8 - Nov 9
On the University of the South campus, Sewanee, TN.
A modern kitchen with white cabinets, a black refrigerator, and a dining area with two black chairs and a white fluffy rug.

18. Tiny Haven at the Retreat

Tiny Haven at the Retreat
Monteagle
9.4 out of 10, Exceptional, (23 reviews)
"We loved it."
United States
Todd
The price is ￥10,237
￥30,454 total
includes taxes & fees
Nov 23 - Nov 24
Tiny Haven at the Retreat
A living room with two sofas, a coffee table, a ceiling fan, a flat-screen TV, and a window with curtains.

19. Lakes, Whiskey & More! Charming Home in Tullahoma

Lakes, Whiskey & More! Charming Home in Tullahoma
Tullahoma
10.0 out of 10, Exceptional, (3 reviews)
"This property was perfect. Everything was so close and so convenient to the home. The host was amazing. We had the best time and can’t wait to come back."
United States
Wendy D.
The price is ￥15,592
￥59,195 total
includes taxes & fees
Nov 8 - Nov 9
Lakes, Whiskey & More! Charming Home in Tullahoma
A stone building with a traditional architectural style, featuring a central entrance and multiple windows.

20. Shea's Chalet - Cozy home in Monteagle, TN

Shea's Chalet - Cozy home in Monteagle, TN
Downtown Monteagle
9.8 out of 10, Exceptional, (38 reviews)
"Great place to stay"
United States
Keith J.
The price is ￥10,237
￥44,163 total
includes taxes & fees
Nov 2 - Nov 3
Shea's Chalet - Cozy home in Monteagle, TN
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

The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

8/10 Good
"Cabin was clean and spacious."
Scott 4-night trip
Posted 16 hours ago
The Smokehouse Lodge and Cabins

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
357
Accommodation
309 Vacation Homes
Lowest Price
￥30,297
Highest Price
￥161,723