A calm lake with autumn foliage, a dock, and houses along the shore.

Holiday Homes in Winchester

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Winchester holiday homes

Interior

1. Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp

Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
Winchester
10.0 out of 10, Exceptional, (7 reviews)
"We were only there for 1 night but the house was clean and comfortable and perfectly suited our needs. "
United States
Gwen K.
The price is AU$1,099
includes taxes & fees
11 Sept - 12 Sept
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
Property grounds

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, (38 reviews)
"Very nice! "
United States
Adam H.
The price is AU$1,122
includes taxes & fees
15 Sept - 16 Sept
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
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 AU$1,484
includes taxes & fees
15 Sept - 16 Sept
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.
Lakefront Lodge on Tims Ford Lake
Living area

5. 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 AU$1,061
includes taxes & fees
15 Sept - 16 Sept
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
Interior

6. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (24 reviews)
"Great stay "
United States
D K.
The price is AU$292
includes taxes & fees
7 Sept - 8 Sept
Whiskey Trails Cottage
Living area

7. 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 AU$627
includes taxes & fees
15 Sept - 16 Sept
Treetop Mountain Retreat Near Sewanee | Sleeps 6
Interior

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, (10 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 AU$272
includes taxes & fees
9 Sept - 10 Sept
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
Dining

9. 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 AU$274
includes taxes & fees
4 Sept - 5 Sept
Spacious private guesthouse within minutes of Tims Ford Lake and Woods Reservoir
Private kitchen

10. 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, (37 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 AU$367
includes taxes & fees
2 Sept - 3 Sept
Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
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, (8 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 AU$354
includes taxes & fees
2 Sept - 3 Sept
Cove Sweet Cove - 3BR + 2BR Near the Caverns!
Interior

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, (50 reviews)
"Good host and property."
United States
David C.
The price is AU$293
includes taxes & fees
2 Sept - 3 Sept
Mountain Memories to provide a cozy retreat on your vacation!
Terrace/patio

13. Sewanee, Caverns,Waterfalls, Hike : Basecamp Tiny

Sewanee, Caverns,Waterfalls, Hike : Basecamp Tiny
Monteagle
10.0 out of 10, Exceptional, (82 reviews)
"Smooth check in and out as well as a beautiful property very close to 3 different towns we could explore. Very well-stocked kitchen and clean property. Our host also had great communication. We really enjoyed our stay! Would totally stay here again. "
United States
elizabeth k.
The price is AU$281
includes taxes & fees
13 Sept - 14 Sept
Sewanee, Caverns,Waterfalls, Hike : Basecamp Tiny
Interior

14. 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 AU$272
includes taxes & fees
2 Sept - 3 Sept
Tiny Haven at the Retreat
Living area

15. Tims Ford Lake Home: Screened Porch, EV

Tims Ford Lake Home: Screened Porch, EV
Tullahoma
10.0 out of 10, Exceptional, (5 reviews)
"Excellent stay, beautiful property"
United States
cassie l.
Tims Ford Lake Home: Screened Porch, EV
Living area

16. Hiker's Hangout Monteagle

Hiker's Hangout Monteagle
Monteagle
9.2 out of 10, Wonderful, (14 reviews)
"Super clean, great location and spacious! "
United States
Karen W.
The price is AU$278
includes taxes & fees
7 Sept - 8 Sept
Hiker's Hangout Monteagle
Exterior

17. 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 AU$406
includes taxes & fees
9 Sept - 10 Sept
Shea's Chalet - Cozy home in Monteagle, TN
Living area

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
9.8 out of 10, Exceptional, (14 reviews)
"Nice trails on the property and close proximity to the Caverns"
United States
Rhea D.
The price is AU$262
includes taxes & fees
9 Sept - 10 Sept
Walk to Deer Lick Falls | 12 Minutes to The Caverns | 18 Minutes to Coalmont OHV
Living area

19. 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
Interior

20. High Point Getaway - Monteagle

High Point Getaway - Monteagle
Downtown Monteagle
9.2 out of 10, Wonderful, (27 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 AU$527
includes taxes & fees
14 Sept - 15 Sept
High Point Getaway - 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

Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

10/10 Excellent
"This is our 3rd time to stay here. We love the location."
Cheri J. 3-night trip
Posted 12 days ago
Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
432
Accommodation
351 Holiday Homes
Lowest Price
AU$262
Highest Price
AU$1,484