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
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Winchester holiday homes

Smart TV

1. Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient!

Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient!
Winchester
8.6 out of 10, Excellent, (22 reviews)
"Peaceful, relaxing and pet friendly great location!"
United States
Holly M.
The price is HK$784
HK$2,527 total
includes taxes & fees
17 Aug - 18 Aug
Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient!
Interior

2. 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 HK$2,329
HK$5,582 total
includes taxes & fees
3 Aug - 4 Aug
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
Smart TV, ping pong

3. 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 HK$2,894
HK$5,537 total
includes taxes & fees
5 Aug - 6 Aug
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
Terrace/patio

4. The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort

The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
Winchester
10.0 out of 10, Exceptional, (8 reviews)
"Right on the water and next to the marina, great location! We stayed over Christmas week. We will be returning in the summer so we can enjoy the lake!"
United States
Andy D.
The price is HK$4,581
HK$8,219 total
includes taxes & fees
20 Aug - 21 Aug
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
Outdoor dining

5. 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, (81 reviews)
"We had a great time! "
United States
Cindy O.
The price is HK$4,235
HK$7,529 total
includes taxes & fees
3 Aug - 4 Aug
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
Terrace/patio

6. 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
Property grounds

7. 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, (37 reviews)
"Very nice! "
United States
Adam H.
The price is HK$3,129
HK$5,686 total
includes taxes & fees
4 Aug - 5 Aug
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Coffee/tea maker, fridge, microwave, oven

8. 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, (34 reviews)
"Convenient location. The place was clean. Nice yard, daffodils were in full bloom initiating spring. "
United States
Michael C.
The price is HK$557
HK$2,065 total
includes taxes & fees
10 Aug - 11 Aug
Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
Exterior

9. Tiny Home Getaway near South Cumberland Park

Tiny Home Getaway near South Cumberland Park
Tracy City
The price is HK$565
HK$1,868 total
includes taxes & fees
15 Aug - 16 Aug
Tiny Home Getaway near South Cumberland Park
Interior

10. Queen ensuite room in historic railroad inn & town. Continental breakfast.

Queen ensuite room in historic railroad inn & town. Continental breakfast.
Cowan
9.8 out of 10, Exceptional, (14 reviews)
"Beautiful spot!"
United States
Bennett R.
The price is HK$980
HK$1,137 total
includes taxes & fees
3 Aug - 4 Aug
Queen ensuite room in historic railroad inn & town. Continental breakfast.
Interior

11. 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, (6 reviews)
The price is HK$518
HK$1,510 total
includes taxes & fees
3 Aug - 4 Aug
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
Interior

12. Artsy 1st floor pet-friendly ensuite king in historic railroad inn & town.

Artsy 1st floor pet-friendly ensuite king in historic railroad inn & town.
Cowan
9.4 out of 10, Exceptional, (10 reviews)
"Pretty Inn with lots of character and charm."
United States
Jennifer C.
The price is HK$1,094
HK$1,251 total
includes taxes & fees
3 Aug - 4 Aug
Artsy 1st floor pet-friendly ensuite king in historic railroad inn & town.
Lobby

13. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (24 reviews)
"Great stay "
United States
D K.
The price is HK$618
HK$1,617 total
includes taxes & fees
4 Aug - 5 Aug
Whiskey Trails Cottage
Interior

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

Cove Sweet Cove - 3BR + 2BR Near the Caverns!
Pelham
10.0 out of 10, Exceptional, (4 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 HK$557
HK$1,977 total
includes taxes & fees
10 Aug - 11 Aug
Cove Sweet Cove - 3BR + 2BR Near the Caverns!
Interior

15. 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, (48 reviews)
"Great house! Tons of room, clean, open floorplan, excellent location. Would definitely stay again!"
United States
Anonymous traveller
The price is HK$635
HK$1,510 total
includes taxes & fees
3 Aug - 4 Aug
Mountain Memories to provide a cozy retreat on your vacation!
Interior

16. Tiny Haven at the Retreat

Tiny Haven at the Retreat
Monteagle
9.4 out of 10, Exceptional, (17 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 HK$518
HK$1,510 total
includes taxes & fees
3 Aug - 4 Aug
Tiny Haven at the Retreat
TV, fireplace

17. Hiker's Hangout Monteagle

Hiker's Hangout Monteagle
Monteagle
9.2 out of 10, Wonderful, (13 reviews)
"Super clean, great location and spacious! "
United States
Karen W.
The price is HK$541
HK$1,544 total
includes taxes & fees
3 Aug - 4 Aug
Hiker's Hangout Monteagle
Exterior

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

Shea's Chalet - Cozy home in Monteagle, TN
Downtown Monteagle
9.8 out of 10, Exceptional, (32 reviews)
"Such a beautiful property and the staff is so kind and responsive"
United States
Jessica
The price is HK$596
HK$2,302 total
includes taxes & fees
10 Aug - 11 Aug
Shea's Chalet - Cozy home in Monteagle, TN
Smart TV, fireplace

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
9.8 out of 10, Exceptional, (12 reviews)
"Nice trails on the property and close proximity to the Caverns"
United States
Rhea D.
The price is HK$510
HK$1,456 total
includes taxes & fees
3 Aug - 4 Aug
Walk to Deer Lick Falls | 12 Minutes to The Caverns | 18 Minutes to Coalmont OHV
Terrace/patio

20. Caverns,Sewanee, Hikes,Waterfalls : Tiny Basecamp

Caverns,Sewanee, Hikes,Waterfalls : Tiny Basecamp
Monteagle
10.0 out of 10, Exceptional, (78 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 HK$769
HK$1,592 total
includes taxes & fees
9 Aug - 10 Aug
Caverns,Sewanee, Hikes,Waterfalls : Tiny Basecamp
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

Spacious Family Gem: Golf Cart - 2 Ensuites - Pool

Spacious Family Gem: Golf Cart - 2 Ensuites - Pool

10/10 Excellent
"Everything was great. Super clean, great screened-in porch, comfy beds, and plenty of space. There was some confusion around the golf cart. The title of the post makes it look like it came with the property, but the text below says there was an extra fee. We worked it out with the owners, but then a battery issue left us pushing it from the marina back to the house."
Paul R. 4-night trip
Posted 2 days ago
Spacious Family Gem: Golf Cart - 2 Ensuites - Pool

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
419
Accommodation
365 Vacation Homes
Lowest Price
HK$1,137
Highest Price
HK$8,219

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