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

A modern kitchen with a built-in coffee maker, a sliding glass door leading to an outdoor patio with a table and chairs.

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 €693
includes taxes & fees
13 Sept - 14 Sept
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
A marina with boats docked, a dock with a covered area, and a sunset over water.

2. Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home

Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
3.0 star property
Winchester
Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
A spacious living room with a large flat-screen TV, comfortable seating, a dining area, and a staircase leading to an upper level.

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 €674
includes taxes & fees
13 Sept - 14 Sept
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
A covered deck with white furniture and blue cushions, overlooking a lake with a house in the background.

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 €969
includes taxes & fees
13 Sept - 14 Sept
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
A wooden deck with outdoor seating and a view of a lake.

5. 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
A wooden deck with a picnic table and chairs, surrounded by windows and a railing.

6. 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 €945
includes taxes & fees
13 Sept - 14 Sept
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
A lakeside view with a wooden dock, a grassy area with a gazebo, and a building with multiple windows in the background.

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, (38 reviews)
"Very nice! "
United States
Adam H.
The price is €714
includes taxes & fees
8 Sept - 9 Sept
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
A modern living room with a wooden dining table, bar stools, and a sofa. A television is mounted on the wall, and there is a large mirror reflecting the room.

8. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (24 reviews)
"Great stay "
United States
D K.
The price is €181
includes taxes & fees
1 Sept - 2 Sept
Whiskey Trails Cottage
A cozy living area with a fireplace, a sofa, a dining table, and a kitchen with brick walls.

9. 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 €171
includes taxes & fees
1 Sept - 2 Sept
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
A modern living room with a TV, wooden flooring, and a large window offering a view of greenery.

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 €409
includes taxes & fees
13 Sept - 14 Sept
Treetop Mountain Retreat Near Sewanee | Sleeps 6
A dining area with a round table and four chairs, a kitchen in the background, and a blue patterned rug.

11. 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 €173
includes taxes & fees
1 Sept - 2 Sept
Spacious private guesthouse within minutes of Tims Ford Lake and Woods Reservoir
A modern kitchen with white cabinets, a wooden ladder, and a blue sofa in a living area with a view of trees.

12. 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 €172
includes taxes & fees
8 Sept - 9 Sept
Hiker's Hangout Monteagle
A modern kitchen with white cabinets, a black refrigerator, and a dining area with two black chairs and a white fluffy rug.

13. 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 €169
includes taxes & fees
13 Sept - 14 Sept
Tiny Haven at the Retreat
A stone building with a traditional architectural style, featuring a central entrance and multiple windows.

14. 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 €252
includes taxes & fees
13 Sept - 14 Sept
Shea's Chalet - Cozy home in Monteagle, TN
A hallway with a wooden floor, a welcome sign, a mirror, and a potted plant.

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, (50 reviews)
"Good host and property."
United States
David C.
The price is €182
includes taxes & fees
1 Sept - 2 Sept
Mountain Memories to provide a cozy retreat on your vacation!
A cabin with a large glass front, surrounded by a gravel path and rock border, set in a forested area with string lights.

16. 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 €175
includes taxes & fees
1 Sept - 2 Sept
Sewanee, Caverns,Waterfalls, Hike : Basecamp Tiny
A white house with a covered porch, stone pathway, and outdoor seating.

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.
Forest Retreat: Poolside Bliss Close to Campus
A modern kitchen with grey cabinets, a central island with a red flower arrangement, and a "FAMILY" sign above the sink.

18. 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 €228
includes taxes & fees
13 Sept - 14 Sept
Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
A modern kitchen with white cabinetry, a central island with bar stools, a built-in TV, and a fireplace.

19. Nesthaven: A cozy boho-chic tiny home with a deck, fire pit, & nearby waterfall

Nesthaven: A cozy boho-chic tiny home with a deck, fire pit, & nearby waterfall
Monteagle
10.0 out of 10, Exceptional, (34 reviews)
"Wonderful property in a safe gated area. Really enjoyed our stay! Really close to Caverns venue, and we enjoyed a beautiful hike to the waterfall. "
United States
Emily S.
The price is €269
includes taxes & fees
10 Sept - 11 Sept
Nesthaven: A cozy boho-chic tiny home with a deck, fire pit, & nearby waterfall
A spacious living room with a grey sofa, a coffee table, and a TV on a stand. There is a kitchen area with white cabinets and a bar.

20. 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.
The price is €410
includes taxes & fees
1 Sept - 2 Sept
Tims Ford Lake Home: Screened Porch, EV
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 11 days ago
Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
434
Accommodation
351 Holiday Homes
Lowest Price
€169
Highest Price
€969