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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Winchester vacation homes

Property grounds

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)
"Very nice! "
United States
Adam H.
The price is AED 37
AED 1,145 total
includes taxes & fees
5 Oct - 6 Oct
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
TV

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

*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
Winchester
The price is AED 420
AED 1,904 total
includes taxes & fees
24 Sep - 25 Sep
*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
Outdoor dining

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, (82 reviews)
"We had a great time! "
United States
Cindy O.
The price is AED 1,983
AED 4,027 total
includes taxes & fees
24 Sep - 25 Sep
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
Smart TV

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 1,286
AED 2,874 total
includes taxes & fees
27 Sep - 28 Sep
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
Interior

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 AED 242
AED 707 total
includes taxes & fees
24 Sep - 25 Sep
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
Interior

6. 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 AED 261
AED 922 total
includes taxes & fees
24 Sep - 25 Sep
Cove Sweet Cove - 3BR + 2BR Near the Caverns!
Coffee/tea maker, fridge, microwave, oven

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 261
AED 964 total
includes taxes & fees
24 Sep - 25 Sep
Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
Terrace/patio

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

Sewanee•Caverns•Waterfalls•Hikes • Tiny Basecamp
Monteagle
10.0 out of 10, Exceptional, (86 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 AED 360
AED 738 total
includes taxes & fees
24 Sep - 25 Sep
Sewanee•Caverns•Waterfalls•Hikes • Tiny Basecamp
Interior

9. 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 AED 242
AED 707 total
includes taxes & fees
24 Sep - 25 Sep
Tiny Haven at the Retreat
Exterior

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

Shea's Chalet - Cozy home in Monteagle, TN
Downtown Monteagle
9.8 out of 10, Exceptional, (35 reviews)
"Great place to stay"
United States
Keith J.
The price is AED 242
AED 1,023 total
includes taxes & fees
24 Sep - 25 Sep
Shea's Chalet - Cozy home in Monteagle, TN
TV, fireplace

11. 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 AED 242
AED 711 total
includes taxes & fees
27 Sep - 28 Sep
Hiker's Hangout Monteagle
TV

12. 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
24 Sep - 25 Sep
Treetop Mountain Retreat Near Sewanee | Sleeps 6
Interior

13. 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, (51 reviews)
"Good host and property."
United States
David C.
The price is AED 298
AED 760 total
includes taxes & fees
29 Sep - 30 Sep
Mountain Memories to provide a cozy retreat on your vacation!
Interior

14. High Point Getaway - Monteagle

High Point Getaway - Monteagle
Downtown Monteagle
9.4 out of 10, Exceptional, (28 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 AED 422
AED 1,388 total
includes taxes & fees
5 Oct - 6 Oct
High Point Getaway - Monteagle
Exterior detail

15. 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 356
AED 849 total
includes taxes & fees
4 Oct - 5 Oct
Whiskey Trails Cottage
TV

16. Heavensent Tiny Home @ The Retreat at Water's Edge - Lake Views!

Heavensent Tiny Home @ The Retreat at Water's Edge - Lake Views!
Tracy City
10.0 out of 10, Exceptional, (78 reviews)
"This was a wonderful cottage in the woods. Beautiful lakeside location, very easy to get to and a wonderful stay"
United States
ERIC C.
The price is AED 364
AED 967 total
includes taxes & fees
24 Sep - 25 Sep
Heavensent Tiny Home @ The Retreat at Water's Edge - Lake Views!
Smart TV, fireplace, music library, video library

17. 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 468
AED 1,310 total
includes taxes & fees
28 Sep - 29 Sep
Tims Ford Lake Home: Screened Porch, EV
Property grounds

18. 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, (11 reviews)
"Very nice property great little getaway overall very nice"
United States
john b.
The price is AED 228
AED 669 total
includes taxes & fees
27 Sep - 28 Sep
Walk to Deer Lick Falls | 12 Minutes to The Caverns | 18 Minutes to Coalmont OHV
Coffee/tea maker, fridge, microwave, oven

19. Time Well Wasted on the Lake

Time Well Wasted on the Lake
Tracy City
9.0 out of 10, Wonderful, (11 reviews)
"Great place, loved the screened in porch! Very clean, had everything we needed "
United States
John E.
The price is AED 327
AED 847 total
includes taxes & fees
24 Sep - 25 Sep
Time Well Wasted on the Lake
Exterior

20. Foster’s Cabin 2 | 2 Minutes from Foster Falls

Foster’s Cabin 2 | 2 Minutes from Foster Falls
Sequatchie
10.0 out of 10, Exceptional, (10 reviews)
"Yes, my dog loved the place! "
United States
Christina G.
The price is AED 290
AED 631 total
includes taxes & fees
5 Oct - 6 Oct
Foster’s Cabin 2 | 2 Minutes from Foster Falls
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
"Everything was great. Location to the Caverns and other adventures was awesome!"
Misty 2-night trip
Posted 20 hours ago
The Smokehouse Lodge and Cabins

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