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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Winchester vacation homes

TV

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

*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
Winchester
The price is AED 735
AED 2,307 total
includes taxes & fees
20 Sep - 21 Sep
*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
Smart TV

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 AED 1,286
AED 2,874 total
includes taxes & fees
28 Sep - 29 Sep
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
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 3,921 total
includes taxes & fees
1 Oct - 2 Oct
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
Terrace/patio

4. 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 AED 2,571
AED 4,313 total
includes taxes & fees
20 Sep - 21 Sep
Lakefront Lodge on Tims Ford Lake
Property grounds

5. 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 1,131 total
includes taxes & fees
5 Oct - 6 Oct
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Exterior detail

6. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (25 reviews)
"Great stay "
United States
D K.
Whiskey Trails Cottage
Interior

7. 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, (12 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 239
AED 707 total
includes taxes & fees
20 Sep - 21 Sep
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
Dining

8. 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.
Spacious private guesthouse within minutes of Tims Ford Lake and Woods Reservoir
Coffee/tea maker, fridge, microwave, oven

9. 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 AED 257
AED 956 total
includes taxes & fees
30 Sep - 1 Oct
Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
TV

10. 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 1,696 total
includes taxes & fees
20 Sep - 21 Sep
Treetop Mountain Retreat Near Sewanee | Sleeps 6
Interior

11. 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 AED 257
AED 922 total
includes taxes & fees
19 Sep - 20 Sep
Cove Sweet Cove - 3BR + 2BR Near the Caverns!
TV, books

12. 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.
Lakes, Whiskey & More! Charming Home in Tullahoma
TV, fireplace

13. Hiker's Hangout Monteagle

Hiker's Hangout Monteagle
Monteagle
9.2 out of 10, Wonderful, (15 reviews)
"Super clean, great location and spacious! "
United States
Karen W.
The price is AED 239
AED 707 total
includes taxes & fees
20 Sep - 21 Sep
Hiker's Hangout Monteagle
Interior

14. 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
21 Sep - 22 Sep
Mountain Memories to provide a cozy retreat on your vacation!
Interior

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 AED 239
AED 707 total
includes taxes & fees
20 Sep - 21 Sep
Tiny Haven at the Retreat
Terrace/patio

16. 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 AED 360
AED 738 total
includes taxes & fees
23 Sep - 24 Sep
Sewanee•Caverns•Waterfalls•Hikes • Tiny Basecamp
Outdoor dining

17. 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 1,998 total
includes taxes & fees
20 Sep - 21 Sep
Forest Retreat: Poolside Bliss Close to Campus
Smart TV, fireplace, music library, video library

18. 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 837
AED 1,790 total
includes taxes & fees
1 Oct - 2 Oct
Tims Ford Lake Home: Screened Porch, EV
Exterior

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, (35 reviews)
"Great place to stay"
United States
Keith J.
The price is AED 239
AED 1,019 total
includes taxes & fees
23 Sep - 24 Sep
Shea's Chalet - Cozy home in Monteagle, TN
Exterior

20. 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 389
AED 922 total
includes taxes & fees
29 Sep - 30 Sep
Lynchburg Getaway walking distance 2 Jack Daniel’s
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

Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

8/10 Good
"We brought our own kayak and the location and lake access were great. Quiet area for paddling. Nice home and space. Well stocked. Couch and stairs to basement need some repairs."
Melanie 4-night trip
Posted 17 hours ago
Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

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