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
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Winchester vacation homes

A living room with a flat-screen TV, a sofa, a coffee table, and a dining area with a small table and chairs.

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

*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
Winchester
The price is ￥30,722
￥95,853 total
includes taxes & fees
Sep 13 - Sep 14
*NEW* Shoreline Escape: Lakefront Retreat w/ 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.

2. 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, (25 reviews)
"What a lovely property and the perfect stay for a large family! We had a great time and the host is very gracious and accommodating. The home was well stocked and had all of the amenities we could have wanted. We had no issues, but the host was very communicative and I'm confident any issue would have been resolved promptly. I highly recommend this home, as well as any other listings from this host!"
United States
Lisa A.
The price is ￥53,764
￥119,100 total
includes taxes & fees
Sep 13 - Sep 14
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
A wooden deck with outdoor seating and a view of a lake.

3. Lakefront Lodge on Tims Ford Lake

Lakefront Lodge on Tims Ford Lake
Winchester
10.0 out of 10, Exceptional, (20 reviews)
"This is a fabulous lake house! The view and amenities are perfect! "
United States
Andrea M.
The price is ￥107,527
￥180,377 total
includes taxes & fees
Sep 15 - Sep 16
Lakefront Lodge on Tims Ford Lake
A wooden deck with a picnic table and chairs, surrounded by windows and a railing.

4. 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, (82 reviews)
"We had a great time! "
United States
Cindy O.
The price is ￥82,949
￥168,433 total
includes taxes & fees
Sep 13 - Sep 14
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
A modern kitchen with white cabinets, a black countertop, and a central island with chairs.

5. Cove Sweet Cove! Fire pit, Fishing, Lake Fun!

Cove Sweet Cove! Fire pit, Fishing, Lake Fun!
Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Loved our stay, the place was great and super clean. Host was very responsive, would definitely stay here again."
United States
Taylor K.
The price is ￥90,622
￥163,347 total
includes taxes & fees
Sep 14 - Sep 15
Cove Sweet Cove! Fire pit, Fishing, Lake Fun!
A lakeside view with a wooden dock, a grassy area with a gazebo, and a building with multiple windows in the background.

6. 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, (38 reviews)
"Very nice! "
United States
Adam H.
The price is ￥61,290
￥125,964 total
includes taxes & fees
Sep 13 - Sep 14
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
A rustic building with a sign reading "Visitor Center" and "Distillery Tour".

7. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (24 reviews)
"Great stay "
United States
D K.
The price is ￥12,097
￥31,676 total
includes taxes & fees
Sep 13 - Sep 14
Whiskey Trails Cottage
A cozy living area with a fireplace, a sofa, a dining table, and a kitchen with brick walls.

8. 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, (11 reviews)
"Nice place to stay. Close to the caverns where we saw a show. Property is very clean. Really nice stay."
United States
Dawn
The price is ￥10,138
￥29,573 total
includes taxes & fees
Sep 13 - Sep 14
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
A modern living room with a TV, wooden flooring, and a large window offering a view of greenery.

9. 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 ￥17,358
￥70,449 total
includes taxes & fees
Sep 13 - Sep 14
Treetop Mountain Retreat Near Sewanee | Sleeps 6
A dining area with a round table and four chairs, a kitchen in the background, and a blue patterned rug.

10. 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 ￥23,042
￥29,859 total
includes taxes & fees
Sep 14 - Sep 15
Spacious private guesthouse within minutes of Tims Ford Lake and Woods Reservoir
A modern kitchen with grey cabinets, a central island with a red flower arrangement, and a "FAMILY" sign above the sink.

11. 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, (38 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 ￥10,906
￥40,301 total
includes taxes & fees
Sep 13 - Sep 14
Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
A cozy living room with a fireplace, wooden flooring, a sofa, and a sliding glass door leading to an outdoor area.

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

Cove Sweet Cove - 3BR + 2BR Near the Caverns!
Pelham
9.8 out of 10, Exceptional, (10 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 ￥10,906
￥38,568 total
includes taxes & fees
Sep 13 - Sep 14
Cove Sweet Cove - 3BR + 2BR Near the Caverns!
A modern kitchen with white cabinets, a black refrigerator, and a dining area with two black chairs and a white fluffy rug.

13. Tiny Haven at the Retreat

Tiny Haven at the Retreat
Monteagle
9.4 out of 10, Exceptional, (19 reviews)
"Tiny Haven was exactly as it was described and was a perfect spot for my family to relax after long days hiking and swimming. The beds are super comfortable and we had everything we needed to make the stay perfect. We enjoyed all the deer that stopped through to check us out. We would definitely stay here again if in the area. Highly recommend!"
United States
Kathleen
The price is ￥10,138
￥29,573 total
includes taxes & fees
Sep 16 - Sep 17
Tiny Haven at the Retreat
A cabin with a large glass front, surrounded by a gravel path and rock border, set in a forested area with string lights.

14. Sewanee•Caverns•Waterfalls•Hikes • Tiny Basecamp

Sewanee•Caverns•Waterfalls•Hikes • Tiny Basecamp
Monteagle
10.0 out of 10, Exceptional, (85 reviews)
"We enjoyed our stay at Tiny Mojo. It was conveniently located to the Caverns, Sewanee, and lots of hiking. The host was very helpful and the house was very clean and comfortable."
United States
Kelley P.
The price is ￥15,054
￥30,876 total
includes taxes & fees
Sep 13 - Sep 14
Sewanee•Caverns•Waterfalls•Hikes • Tiny Basecamp
A white house with a covered porch, stone pathway, and outdoor seating.

15. Forest Retreat: Poolside Bliss Close to Campus

Forest Retreat: Poolside Bliss Close to Campus
Sewanee
10.0 out of 10, Exceptional, (12 reviews)
"Lovely home in a great location"
United States
Denise M.
The price is ￥25,645
￥83,570 total
includes taxes & fees
Sep 15 - Sep 16
Forest Retreat: Poolside Bliss Close to Campus
A large building with a covered entrance and a sign that reads "Welcome".

16. Lynchburg Getaway walking distance 2 Jack Daniel’s

Lynchburg Getaway walking distance 2 Jack Daniel’s
Lynchburg
10.0 out of 10, Exceptional, (38 reviews)
"We really enjoyed our stay and it was very conveniently located to the downtown area"
United States
Hildegard
The price is ￥14,931
￥36,840 total
includes taxes & fees
Sep 15 - Sep 16
Lynchburg Getaway walking distance 2 Jack Daniel’s
A living room with two sofas, a coffee table, a ceiling fan, a flat-screen TV, and a window with curtains.

17. 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 ￥13,518
￥55,447 total
includes taxes & fees
Sep 26 - Sep 27
Lakes, Whiskey & More! Charming Home in Tullahoma
A stone building with a traditional architectural style, featuring a central entrance and multiple windows.

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

Shea's Chalet - Cozy home in Monteagle, TN
Downtown Monteagle
9.8 out of 10, Exceptional, (34 reviews)
"Great place to stay"
United States
Keith J.
The price is ￥10,138
￥42,799 total
includes taxes & fees
Sep 22 - Sep 23
Shea's Chalet - Cozy home in Monteagle, TN
A hallway with a wooden floor, a welcome sign, a mirror, and a potted plant.

19. Mountain Memories to provide a cozy retreat on your vacation!

Mountain Memories to provide a cozy retreat on your vacation!
Monteagle
9.4 out of 10, Exceptional, (50 reviews)
"Good host and property."
United States
David C.
The price is ￥12,442
￥31,768 total
includes taxes & fees
Sep 15 - Sep 16
Mountain Memories to provide a cozy retreat on your vacation!
A modern kitchen with white cabinetry, stainless steel appliances, a large island with a black countertop, and a wooden floor.

20. Tullahoma Whiskey Trail Base w/ Yard & Fire Pit

Tullahoma Whiskey Trail Base w/ Yard & Fire Pit
Tullahoma
10.0 out of 10, Exceptional, (2 reviews)
"great hosts and location!"
United States
Jaren B.
The price is ￥22,734
￥76,132 total
includes taxes & fees
Sep 17 - Sep 18
Tullahoma Whiskey Trail Base w/ Yard & Fire Pit
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

10/10 Excellent
"The room was clean. The facility quiet. The staff was very friendly. The beds were comfortable and free of stains. Will stay here again in the future!"
Jessica 2-night trip
Posted 3 hours ago
The Smokehouse Lodge and Cabins

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
7,954
Accommodation
329 Vacation Homes
Lowest Price
￥7,522
Highest Price
￥36,026