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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Winchester vacation 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
The price is AED 275
AED 1,184 total
includes taxes & fees
27 Oct - 28 Oct
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 AED 37
AED 1,164 total
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
10.0 out of 10, Exceptional, (1 review)
"This was the perfect place for our family of five to use while visiting University of the South!! We weren’t able to take advantage of the hot tub or kayaks but we did wander the property and take advantage of the beautiful water views.Make sure to visit the Sunrise Cafe while you are there! Order a plate of cinnamon role pancakes for the table!! Delicious."
United States
Vonda R.
The price is AED 444
AED 1,935 total
includes taxes & fees
2 Nov - 3 Nov
*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 AED 1,082
AED 3,720 total
includes taxes & fees
25 Oct - 26 Oct
Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
Dining

5. The Lakeside Getaway

The Lakeside Getaway
Winchester
9.8 out of 10, Exceptional, (6 reviews)
"Incredible "
United States
Jim C.
The price is AED 262
AED 1,700 total
includes taxes & fees
23 Oct - 24 Oct
The Lakeside Getaway
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, (83 reviews)
"We had a great time! "
United States
Cindy O.
The price is AED 1,488
AED 3,381 total
includes taxes & fees
1 Nov - 2 Nov
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.

7. 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 AED 1,286
AED 2,874 total
includes taxes & fees
25 Oct - 26 Oct
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
A modern living room with a TV, wooden flooring, and a large window offering a view of greenery.

8. 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.
Treetop Mountain Retreat Near Sewanee | Sleeps 6
A bed with a patterned bedspread, two grey pillows, and two bedside tables with lamps and potted plants.

9. Whiskey Trails Cottage

Whiskey Trails Cottage
Tullahoma
10.0 out of 10, Exceptional, (26 reviews)
"Great place to stay. Had everything we needed. Great location."
United States
Jennifer T.
The price is AED 289
AED 757 total
includes taxes & fees
25 Oct - 26 Oct
Whiskey Trails Cottage
A modern kitchen with grey cabinets, a central island with a red flower arrangement, and a "FAMILY" sign above the sink.

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, (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 AED 261
AED 967 total
includes taxes & fees
27 Oct - 28 Oct
Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!
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, (16 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 264
AED 740 total
includes taxes & fees
26 Oct - 27 Oct
Partin's Perch | Indoor Private Sauna | 9 Min from 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.

12. 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 508
AED 1,367 total
includes taxes & fees
25 Oct - 26 Oct
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.

13. 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)
"Great house and even better location! Will be staying again!!"
United States
Courtney C.
The price is AED 1,561
AED 3,235 total
includes taxes & fees
1 Nov - 2 Nov
Lake Life 4 Bedroom, 3 Bath, Sleeps 12.
A white house with a covered porch, stone pathway, and outdoor seating.

14. Forest Retreat: Poolside Bliss Close to Campus

Forest Retreat: Poolside Bliss Close to Campus
Sewanee
10.0 out of 10, Exceptional, (13 reviews)
"Lovely home in a great location"
United States
Denise M.
The price is AED 609
AED 1,983 total
includes taxes & fees
25 Oct - 26 Oct
Forest Retreat: Poolside Bliss Close to Campus
A cozy living room with a fireplace, wooden flooring, a sofa, and a sliding glass door leading to an outdoor area.

15. 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 AED 257
AED 925 total
includes taxes & fees
2 Nov - 3 Nov
Cove Sweet Cove - 3BR + 2BR Near the Caverns!
A living room with two sofas, a coffee table, a ceiling fan, a flat-screen TV, and a window with curtains.

16. 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.
The price is AED 323
AED 1,329 total
includes taxes & fees
23 Oct - 24 Oct
Lakes, Whiskey & More! Charming Home in Tullahoma
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 AED 242
AED 711 total
includes taxes & fees
27 Oct - 28 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 AED 1,010
AED 2,134 total
includes taxes & fees
25 Oct - 26 Oct
Holiday House
A cozy living room with a sofa, armchair, and ottoman, wooden walls, and large windows with curtains.

19. 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, (35 reviews)
"wonderful place to stay right on Sewanee's campus!"
United States
katherine v.
The price is AED 1,121
AED 2,182 total
includes taxes & fees
27 Oct - 28 Oct
On the University of the South campus, Sewanee, TN.
A hallway with a wooden floor, a welcome sign, a mirror, and a potted plant.

20. 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, (52 reviews)
"Good host and property."
United States
David C.
The price is AED 298
AED 767 total
includes taxes & fees
26 Oct - 27 Oct
Mountain Memories to provide a cozy retreat on your vacation!
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

Microtel Inn & Suites by Wyndham Manchester

Microtel Inn & Suites by Wyndham Manchester

10/10 Excellent
"close parking"
Jim 1-night trip
Posted less than an hour ago
Microtel Inn & Suites by Wyndham Manchester

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