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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Winchester holiday homes

A bedroom with a bed, a dresser, a TV, and a view of a golf course through an open door.

1. Iconic Winchester home near Tims Ford State Park!

Iconic Winchester home near Tims Ford State Park!
Winchester
Iconic Winchester home near Tims Ford State Park!
A lakeside view with a wooden dock, a grassy area with a gazebo, and a building with multiple windows in the background.

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, (39 reviews)
"Great property!"
United States
Greg B.
The price is €287
includes taxes & fees
31 Oct - 1 Nov
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
A stainless steel outdoor grill with four burners, a chimney, and a control panel, set against a wooden fence and surrounded by trees.

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

*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
Winchester
The price is €489
includes taxes & fees
28 Oct - 29 Oct
*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
A marina with boats docked, a dock with a covered area, and a sunset over water.

4. 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
The price is €929
includes taxes & fees
18 Oct - 19 Oct
Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
A wooden deck with a picnic table and chairs, surrounded by windows and a railing.

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, (83 reviews)
"We had a great time! "
United States
Cindy O.
The price is €976
includes taxes & fees
29 Oct - 30 Oct
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
A spacious living room with a large flat-screen TV, comfortable seating, a dining area, and a staircase leading to an upper level.

6. 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, (27 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 €699
includes taxes & fees
18 Oct - 19 Oct
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
A cozy living room with a sofa, armchair, and ottoman, wooden walls, and large windows with curtains.

7. On the University of the South campus, Sewanee, TN.

On the University of the South campus, Sewanee, TN.
Sewanee
9.8 out of 10, Exceptional, (33 reviews)
"wonderful place to stay right on Sewanee's campus!"
United States
katherine v.
The price is €531
includes taxes & fees
20 Oct - 21 Oct
On the University of the South campus, Sewanee, TN.
A modern kitchen with grey cabinets, a central island with a red flower arrangement, and a "FAMILY" sign above the sink.

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, (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 €239
includes taxes & fees
18 Oct - 19 Oct
Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
A modern living room with a TV, wooden flooring, and a large window offering a view of greenery.

9. 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
20 Oct - 21 Oct
Treetop Mountain Retreat Near Sewanee | Sleeps 6
Island

10. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (26 reviews)
"Great stay "
United States
D K.
The price is €215
includes taxes & fees
29 Oct - 30 Oct
Whiskey Trails Cottage
A cozy living area with a fireplace, a sofa, a dining table, and a kitchen with brick walls.

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, (15 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 €175
includes taxes & fees
26 Oct - 27 Oct
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
A cozy living room with a fireplace, wooden flooring, a sofa, and a sliding glass door leading to an outdoor area.

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

Cove Sweet Cove - 3BR + 2BR Near the Caverns!
Pelham
10.0 out of 10, Exceptional, (13 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 €226
includes taxes & fees
18 Oct - 19 Oct
Cove Sweet Cove - 3BR + 2BR Near the Caverns!
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.

13. 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.
Tims Ford Lake Home: Screened Porch, EV
A spacious living room with a grey sofa, a round wicker chair, and large windows offering a view of trees.

14. Lake Life 4 Bedroom, 3 Bath, Sleeps 12.

Lake Life 4 Bedroom, 3 Bath, Sleeps 12.
Estill Springs
9.8 out of 10, Exceptional, (35 reviews)
"Excellent place to stay for a weekend get away with friends or family "
United States
Zack F.
The price is €737
includes taxes & fees
17 Oct - 18 Oct
Lake Life 4 Bedroom, 3 Bath, Sleeps 12.
A living room with two sofas, a coffee table, a ceiling fan, a flat-screen TV, and a window with curtains.

15. 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
A white house with a covered porch, stone pathway, and outdoor seating.

16. Forest Retreat: Poolside Bliss Close to Campus

Forest Retreat: Poolside Bliss Close to Campus
Sewanee
10.0 out of 10, Exceptional, (13 reviews)
The price is €481
includes taxes & fees
19 Oct - 20 Oct
Forest Retreat: Poolside Bliss Close to Campus
A modern kitchen with white cabinets, a black refrigerator, and a dining area with two black chairs and a white fluffy rug.

17. Tiny Haven at the Retreat

Tiny Haven at the Retreat
Monteagle
9.4 out of 10, Exceptional, (23 reviews)
"We loved it."
United States
Todd
The price is €177
includes taxes & fees
18 Oct - 19 Oct
Tiny Haven at the Retreat
A cozy interior space with a sliding glass door leading to an outdoor deck.

18. Holiday House

Holiday House
Tullahoma
9.6 out of 10, Exceptional, (14 reviews)
"Family friendly"
United States
Trinette N.
The price is €517
includes taxes & fees
29 Oct - 30 Oct
Holiday House
A large building with a covered entrance and a sign that reads "Welcome".

19. Lynchburg Getaway walking distance 2 Jack Daniel’s

Lynchburg Getaway walking distance 2 Jack Daniel’s
Lynchburg
10.0 out of 10, Exceptional, (39 reviews)
The price is €320
includes taxes & fees
15 Nov - 16 Nov
Lynchburg Getaway walking distance 2 Jack Daniel’s
A stone building with a traditional architectural style, featuring a central entrance and multiple windows.

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

Shea's Chalet - Cozy home in Monteagle, TN
Downtown Monteagle
9.8 out of 10, Exceptional, (37 reviews)
"Great place to stay"
United States
Keith J.
The price is €248
includes taxes & fees
19 Oct - 20 Oct
Shea's Chalet - Cozy home in Monteagle, TN
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 was an amazing stay."
Alicia W. 3-night trip
Posted 3 hours ago
Lakehouse 4BR4BA FreeKayaks 2Kitchen DoubleDeck SwimPool BoatRamp FamilyVacation

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
420
Accommodation
311 Holiday Homes
Lowest Price
€175
Highest Price
€976