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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Winchester holiday homes

A lakeside view with a wooden dock, a grassy area with a gazebo, and a building with multiple windows in the background.

1. 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, (40 reviews)
"Great property!"
United States
Greg B.
The price is HK$78
HK$2,485 total
includes taxes & fees
31 Oct - 1 Nov
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
A modern living room with a blue sofa, a staircase, a kitchen, and a fireplace.

2. Iconic Winchester home near Tims Ford State Park!

Iconic Winchester home near Tims Ford State Park!
Winchester
The price is HK$824
HK$3,562 total
includes taxes & fees
10 Nov - 11 Nov
Iconic Winchester home near Tims Ford State Park!
A kitchen with a coffee machine, a sink, and a window with curtains.

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 HK$1,004
HK$4,204 total
includes taxes & fees
10 Nov - 11 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 HK$3,128
HK$8,880 total
includes taxes & fees
30 Oct - 31 Oct
Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
Dining

5. The Lakefront Getaway

The Lakefront Getaway
Winchester
9.8 out of 10, Exceptional, (6 reviews)
"Incredible "
United States
Jim C.
The price is HK$1,161
HK$4,423 total
includes taxes & fees
1 Nov - 2 Nov
The Lakefront 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 HK$3,177
HK$7,221 total
includes taxes & fees
10 Nov - 11 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 HK$2,746
HK$6,137 total
includes taxes & fees
2 Nov - 3 Nov
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.
The price is HK$886
HK$3,621 total
includes taxes & fees
2 Nov - 3 Nov
Treetop Mountain Retreat Near Sewanee | Sleeps 6
A white house with a covered porch, stone pathway, and outdoor seating.

9. 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 HK$1,310
HK$4,244 total
includes taxes & fees
31 Oct - 1 Nov
Forest Retreat: Poolside Bliss Close to Campus
A dining area with a round table and four chairs, a kitchen in the background, and a blue patterned rug.

10. 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.
Spacious private guesthouse within minutes of Tims Ford Lake and Woods Reservoir
A spacious interior with wooden beams, a reception desk, and a sign reading "Welcome to the Family."

11. 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 HK$677
HK$1,693 total
includes taxes & fees
2 Nov - 3 Nov
Whiskey Trails Cottage
A modern kitchen with grey cabinets, a central island with a red flower arrangement, and a "FAMILY" sign above the sink.

12. 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 HK$549
HK$2,057 total
includes taxes & fees
10 Nov - 11 Nov
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.

13. 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, (17 reviews)
"This is going to be my go to spot for all Caverns shows. Comfy, spacious and perfect for my crew of 4. The cafe attached was a nice bonus!"
United States
Andrea
The price is HK$580
HK$1,760 total
includes taxes & fees
2 Nov - 3 Nov
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.

14. 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 HK$1,138
HK$3,004 total
includes taxes & fees
3 Nov - 4 Nov
Tims Ford Lake Home: Screened Porch, EV
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 HK$549
HK$1,961 total
includes taxes & fees
10 Nov - 11 Nov
Cove Sweet Cove - 3BR + 2BR Near the Caverns!
A spacious living room with a grey sofa, a round wicker chair, and large windows offering a view of trees.

16. 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 HK$3,334
HK$6,909 total
includes taxes & fees
11 Nov - 12 Nov
Lake Life 4 Bedroom, 3 Bath, Sleeps 12.
A cozy interior space with a sliding glass door leading to an outdoor deck.

17. Holiday House

Holiday House
Tullahoma
9.6 out of 10, Exceptional, (14 reviews)
"Family friendly"
United States
Trinette N.
The price is HK$2,157
HK$4,559 total
includes taxes & fees
30 Oct - 31 Oct
Holiday House
A living room with two sofas, a coffee table, a ceiling fan, a flat-screen TV, and a window with curtains.

18. 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 HK$777
HK$2,948 total
includes taxes & fees
2 Nov - 3 Nov
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.

19. 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 HK$588
HK$1,762 total
includes taxes & fees
29 Nov - 30 Nov
Tiny Haven at the Retreat
A large building with a covered entrance and a sign that reads "Welcome".

20. Lynchburg Getaway walking distance 2 Jack Daniel’s

Lynchburg Getaway walking distance 2 Jack Daniel’s
Lynchburg
10.0 out of 10, Exceptional, (40 reviews)
"We really enjoyed our stay and it was very conveniently located to the downtown area"
United States
Hildegard
The price is HK$780
HK$2,290 total
includes taxes & fees
2 Nov - 3 Nov
Lynchburg Getaway walking distance 2 Jack Daniel’s
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
"Off the beaten path--by a block, so convenient."
Gregory 2-night trip
Posted 2 days ago
Microtel Inn & Suites by Wyndham Manchester

Find out more about Winchester

Winchester Vacation Homes information

Number of reviews
329
Accommodation
313 Vacation Homes
Lowest Price
HK$1,693
Highest Price
HK$8,880

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