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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Winchester vacation homes

A lakeside view with a wooden dock, a grassy area with a gazebo, and a building with multiple windows in the background.

1. 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.
The price is AED 37
AED 1,145 total
includes taxes & fees
31 Oct - 1 Nov
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
A stainless steel outdoor grill with four burners, a chimney, and a control panel, set against a wooden fence and surrounded by trees.

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

*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
Winchester
The price is AED 522
AED 2,034 total
includes taxes & fees
11 Oct - 12 Oct
*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
A wooden deck with a picnic table and chairs, surrounded by windows and a railing.

3. 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 AED 1,653
AED 3,595 total
includes taxes & fees
1 Nov - 2 Nov
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.

4. 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)
"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 AED 1,466
AED 3,108 total
includes taxes & fees
6 Nov - 7 Nov
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
Island

5. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (26 reviews)
"Great stay "
United States
D K.
The price is AED 386
AED 879 total
includes taxes & fees
6 Nov - 7 Nov
Whiskey Trails Cottage
A modern living room with a TV, wooden flooring, and a large window offering a view of greenery.

6. 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 AED 415
AED 1,685 total
includes taxes & fees
7 Oct - 8 Oct
Treetop Mountain Retreat Near Sewanee | Sleeps 6
A modern kitchen with grey cabinets, a central island with a red flower arrangement, and a "FAMILY" sign above the sink.

7. 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 AED 246
AED 943 total
includes taxes & fees
7 Oct - 8 Oct
Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
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, (14 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 AED 301
AED 782 total
includes taxes & fees
27 Oct - 28 Oct
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
A spacious living room with a grey sofa, a coffee table, and a TV on a stand. There is a kitchen area with white cabinets and a bar.

9. Tims Ford Lake Home: Screened Porch, EV

Tims Ford Lake Home: Screened Porch, EV
Tullahoma
10.0 out of 10, Exceptional, (6 reviews)
"Excellent stay, beautiful property"
United States
cassie l.
The price is AED 496
AED 1,361 total
includes taxes & fees
2 Nov - 3 Nov
Tims Ford Lake Home: Screened Porch, EV
A white house with a covered porch, stone pathway, and outdoor seating.

10. 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 AED 613
AED 1,987 total
includes taxes & fees
8 Oct - 9 Oct
Forest Retreat: Poolside Bliss Close to Campus
A spacious living room with a grey sofa, a round wicker chair, and large windows offering a view of trees.

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

Lake Life 4 Bedroom, 3 Bath, Sleeps 12.
Estill Springs
9.8 out of 10, Exceptional, (34 reviews)
"Excellent place to stay for a weekend get away with friends or family "
United States
Zack F.
The price is AED 1,561
AED 3,235 total
includes taxes & fees
6 Nov - 7 Nov
Lake Life 4 Bedroom, 3 Bath, Sleeps 12.
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
10.0 out of 10, Exceptional, (12 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 AED 257
AED 914 total
includes taxes & fees
20 Oct - 21 Oct
Cove Sweet Cove - 3BR + 2BR Near the Caverns!
A living room with two sofas, a coffee table, a ceiling fan, a flat-screen TV, and a window with curtains.

13. 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 AED 323
AED 1,329 total
includes taxes & fees
6 Nov - 7 Nov
Lakes, Whiskey & More! Charming Home in Tullahoma
A modern kitchen with white cabinets, a black refrigerator, and a dining area with two black chairs and a white fluffy rug.

14. Tiny Haven at the Retreat

Tiny Haven at the Retreat
Monteagle
9.4 out of 10, Exceptional, (22 reviews)
"We loved it."
United States
Todd
Tiny Haven at the Retreat
A cozy interior space with a sliding glass door leading to an outdoor deck.

15. Holiday House

Holiday House
Tullahoma
9.6 out of 10, Exceptional, (14 reviews)
"This house was very nice!"
United States
Brittney L.
The price is AED 1,010
AED 2,134 total
includes taxes & fees
7 Oct - 8 Oct
Holiday House
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 AED 606
AED 1,394 total
includes taxes & fees
6 Nov - 7 Nov
Lynchburg Getaway walking distance 2 Jack Daniel’s
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, (32 reviews)
"wonderful place to stay right on Sewanee's campus!"
United States
katherine v.
The price is AED 1,121
AED 2,182 total
includes taxes & fees
11 Oct - 12 Oct
On the University of the South campus, Sewanee, TN.
A hallway with a wooden floor, a welcome sign, a mirror, and a potted plant.

18. 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, (52 reviews)
"Good host and property."
United States
David C.
The price is AED 298
AED 760 total
includes taxes & fees
7 Oct - 8 Oct
Mountain Memories to provide a cozy retreat on your vacation!
A stone building with a traditional architectural style, featuring a central entrance and multiple windows.

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

Shea's Chalet - Cozy home in Monteagle, TN
Downtown Monteagle
9.8 out of 10, Exceptional, (36 reviews)
"Great place to stay"
United States
Keith J.
The price is AED 239
AED 1,026 total
includes taxes & fees
12 Oct - 13 Oct
Shea's Chalet - Cozy home in Monteagle, TN
A modern kitchen with white cabinets, a wooden ladder, and a blue sofa in a living area with a view of trees.

20. Hiker's Hangout Monteagle

Hiker's Hangout Monteagle
Monteagle
9.2 out of 10, Wonderful, (16 reviews)
"Great property and great location. Check in was easy and smooth."
United States
Amanda B.
The price is AED 202
AED 661 total
includes taxes & fees
7 Oct - 8 Oct
Hiker's Hangout Monteagle
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
"My husband and I originally booked a one bedroom cabin for .two nights but we loved it so much we stayed one extra! Our cabin was rustic, romantic and quiet. The wood burning fireplace, jetted tub and rockers on the covered porch were lovely. The bed was very comfortable with nice linens and the bathroom appeared to be recently updated. There were some cobwebs and the floors could have been cleaner but it all just added character. Our dog loved it as well with plenty of room to run around and the pool was nice to lounge beside. The cookware was sufficient for basic meal prep but better yet there is a fabulous Italian restaurant down the street. There is also a Piggly Wiggly next door with a vast wine and beer selection. My only disappointment was that the on site bar/restaurant is only open on weekends and we didn’t get the opportunity to try it out.we will definitely be back!!!"
Kristy 2-night trip
Posted 15 hours ago
The Smokehouse Lodge and Cabins

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