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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winchester holiday homes

A stainless steel outdoor grill with four burners, a chimney, and a control panel, set against a wooden fence and surrounded by trees.

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

*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
Winchester
The price is £416
includes taxes & fees
12 Oct - 13 Oct
*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
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, (39 reviews)
"Great property!"
United States
Greg B.
The price is £233
includes taxes & fees
5 Oct - 6 Oct
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
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 £824
includes taxes & fees
30 Sept - 1 Oct
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 £588
includes taxes & fees
4 Oct - 5 Oct
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
A cozy living area with a fireplace, a sofa, a dining table, and a kitchen with brick walls.

5. 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 £153
includes taxes & fees
30 Sept - 1 Oct
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
A modern kitchen with grey cabinets, a central island with a red flower arrangement, and a "FAMILY" sign above the sink.

6. 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 £203
includes taxes & fees
30 Sept - 1 Oct
Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
Island

7. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (26 reviews)
"Great stay "
United States
D K.
The price is £153
includes taxes & fees
4 Oct - 5 Oct
Whiskey Trails Cottage
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 £345
includes taxes & fees
30 Sept - 1 Oct
Treetop Mountain Retreat Near Sewanee | Sleeps 6
A cozy living room with a fireplace, wooden flooring, a sofa, and a sliding glass door leading to an outdoor area.

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

Cove Sweet Cove - 3BR + 2BR Near the Caverns!
Pelham
10.0 out of 10, Exceptional, (11 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 £191
includes taxes & fees
6 Oct - 7 Oct
Cove Sweet Cove - 3BR + 2BR Near the Caverns!
A modern kitchen with white cabinets, a wooden ladder, and a blue sofa in a living area with a view of trees.

10. Hiker's Hangout Monteagle

Hiker's Hangout Monteagle
Monteagle
9.2 out of 10, Wonderful, (16 reviews)
"Super clean, great location and spacious! "
United States
Karen W.
The price is £147
includes taxes & fees
28 Oct - 29 Oct
Hiker's Hangout Monteagle
A cabin with a large glass front, surrounded by a gravel path and rock border, set in a forested area with string lights.

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

Sewanee•Caverns•Waterfalls•Hikes • Tiny Basecamp
Monteagle
10.0 out of 10, Exceptional, (87 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 £152
includes taxes & fees
30 Sept - 1 Oct
Sewanee•Caverns•Waterfalls•Hikes • Tiny Basecamp
A hallway with a wooden floor, a welcome sign, a mirror, and a potted plant.

12. 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 £159
includes taxes & fees
5 Oct - 6 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.

13. 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 £210
includes taxes & fees
6 Oct - 7 Oct
Shea's Chalet - Cozy home in Monteagle, TN
A large building with a covered entrance and a sign that reads "Welcome".

14. 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 £217
includes taxes & fees
20 Oct - 21 Oct
Lynchburg Getaway walking distance 2 Jack Daniel’s
A modern kitchen with white cabinets, a black refrigerator, and a dining area with two black chairs and a white fluffy rug.

15. Tiny Haven at the Retreat

Tiny Haven at the Retreat
Monteagle
9.4 out of 10, Exceptional, (20 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 £151
includes taxes & fees
21 Oct - 22 Oct
Tiny Haven at the Retreat
A white house with a covered porch, stone pathway, and outdoor seating.

16. 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 £546
includes taxes & fees
8 Oct - 9 Oct
Forest Retreat: Poolside Bliss Close to Campus
A modern kitchen with a marble countertop, four bar stools, and a hexagonal shelf unit.

17. High Point Getaway - Monteagle

High Point Getaway - Monteagle
Downtown Monteagle
9.2 out of 10, Wonderful, (29 reviews)
"We love staying at this property (the sister property behind this one too). It’s close to everything and within walking distance of several restaurants - big bonus - they allow our dogs to join us too. The big front porch is great for early evenings."
United States
Jennifer S.
The price is £286
includes taxes & fees
6 Oct - 7 Oct
High Point Getaway - Monteagle
A covered outdoor seating area with wicker chairs and a swing set, overlooking a lake.

18. Beautiful Rustic Cabin On Lincoln Lake Is A Sportsman paradise.

Beautiful Rustic Cabin On Lincoln Lake Is A Sportsman paradise.
Kelso
9.8 out of 10, Exceptional, (136 reviews)
"We had a great time fishing and hanging out. The cabin worked out well for our family of 3, and we are planning on coming back at some point in the future."
United States
Tyler H.
The price is £241
includes taxes & fees
1 Oct - 2 Oct
Beautiful Rustic Cabin On Lincoln Lake Is A Sportsman paradise.
A circular stone fire pit with four Adirondack chairs around it, surrounded by a string of lights.

19. Walk to Deer Lick Falls | 12 Minutes to The Caverns | 18 Minutes to Coalmont OHV

Walk to Deer Lick Falls | 12 Minutes to The Caverns | 18 Minutes to Coalmont OHV
Monteagle
10.0 out of 10, Exceptional, (12 reviews)
"Very nice property great little getaway overall very nice"
United States
john b.
The price is £141
includes taxes & fees
30 Sept - 1 Oct
Walk to Deer Lick Falls | 12 Minutes to The Caverns | 18 Minutes to Coalmont OHV
A modern kitchen with grey cabinets, stainless steel appliances, and a wooden ceiling.

20. Lounges at Lynchburg Green House - within walking distance to Jack Daniels!

Lounges at Lynchburg Green House - within walking distance to Jack Daniels!
Lynchburg
10.0 out of 10, Exceptional, (17 reviews)
"Perfect place!"
United States
Jennifer
The price is £153
includes taxes & fees
30 Sept - 1 Oct
Lounges at Lynchburg Green House - within walking distance to Jack Daniels!
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
"Great!"
Ronda 1-night trip
Posted less than an hour ago
The Smokehouse Lodge and Cabins

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
669
Accommodation
313 Holiday Homes
Lowest Price
£141
Highest Price
£824