Winchester Vacation Homes

A calm lake with autumn foliage, a dock, and houses along the shore.

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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

Winchester

Adam H.

HK$2,446 total

includes taxes & fees

5 Oct - 6 Oct

A living room with a flat-screen TV, a sofa, a coffee table, and a dining area with a small table and chairs.

2. NEW Shoreline Escape: Lakefront Retreat w/ Hot Tub

Winchester

HK$4,927 total

includes taxes & fees

27 Sept - 28 Sept

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

3. Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub

Winchester

Cindy O.

HK$8,602 total

includes taxes & fees

23 Sept - 24 Sept

A spacious living room with a large flat-screen TV, comfortable seating, a dining area, and a staircase leading to an upper level.

4. Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12

Winchester

"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!"

Lisa A.

HK$5,980 total

includes taxes & fees

19 Oct - 20 Oct

A cozy living area with a fireplace, a sofa, a dining table, and a kitchen with brick walls.

5. Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns

Pelham

Dawn

HK$1,501 total

includes taxes & fees

23 Sept - 24 Sept

A cozy living room with a fireplace, wooden flooring, a sofa, and a sliding glass door leading to an outdoor area.

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

Pelham

Joanne G.

HK$1,953 total

includes taxes & fees

23 Sept - 24 Sept

A modern kitchen with grey cabinets, a central island with a red flower arrangement, and a "FAMILY" sign above the sink.

7. Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!

Pelham

Antonio M.

HK$2,300 total

includes taxes & fees

23 Oct - 24 Oct

A cabin with a large glass front, surrounded by a gravel path and rock border, set in a forested area with string lights.

8. Sewanee•Caverns•Waterfalls•Hikes • Tiny Basecamp

Monteagle

Kelley P.

HK$1,577 total

includes taxes & fees

23 Sept - 24 Sept

A stone building with a traditional architectural style, featuring a central entrance and multiple windows.

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

Downtown Monteagle

Keith J.

HK$2,176 total

includes taxes & fees

23 Sept - 24 Sept

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

Sewanee

Lisa C.

HK$3,598 total

includes taxes & fees

23 Sept - 24 Sept

A modern kitchen with white cabinets, a wooden ladder, and a blue sofa in a living area with a view of trees.

11. Hiker's Hangout Monteagle

Monteagle

Karen W.

HK$1,509 total

includes taxes & fees

27 Sept - 28 Sept

A circular stone fire pit with four Adirondack chairs around it, surrounded by a string of lights.

12. Walk to Deer Lick Falls | 12 Minutes to The Caverns | 18 Minutes to Coalmont OHV

Monteagle

john b.

HK$1,421 total

includes taxes & fees

23 Sept - 24 Sept

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

Monteagle

Kathleen

HK$1,510 total

includes taxes & fees

24 Sept - 25 Sept

A hallway with a wooden floor, a welcome sign, a mirror, and a potted plant.

14. Mountain Memories to provide a cozy retreat on your vacation!

Monteagle

David C.

HK$1,622 total

includes taxes & fees

30 Sept - 1 Oct

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.

15. Tims Ford Lake Home: Screened Porch, EV

Tullahoma

cassie l.

HK$2,711 total

includes taxes & fees

23 Sept - 24 Sept

A rustic building with a sign reading "Visitor Center" and "Distillery Tour".

16. Whiskey Trails Cottage

Tullahoma

D K.

HK$1,893 total

includes taxes & fees

4 Oct - 5 Oct

A modern kitchen with a marble countertop, four bar stools, and a hexagonal shelf unit.

17. High Point Getaway - Monteagle

Downtown Monteagle

Jennifer S.

HK$2,973 total

includes taxes & fees

23 Sept - 24 Sept

A modern living room with a ceiling fan, a sofa, a coffee table, and a door with a wreath.

18. Heavensent Tiny Home @ The Retreat at Water's Edge - Lake Views!

Tracy City

ERIC C.

HK$2,066 total

includes taxes & fees

23 Sept - 24 Sept

A modern cabin with a wooden exterior, a porch with steps, and two chairs.

19. Foster’s Cabin 2 | 2 Minutes from Foster Falls

Sequatchie

Christina G.

HK$1,403 total

includes taxes & fees

23 Sept - 24 Sept

A modern kitchen with white cabinetry, a central island, stainless steel appliances, and a black and gold chair.

20. Time Well Wasted on the Lake

Tracy City

John E.

HK$1,791 total

includes taxes & fees

23 Sept - 24 Sept

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Top Winchester Hotel Reviews

Spark by Hilton Kimball

8/10 Good

"Room was clean, AC worked well! Shower drained and bed was very comfortable."

Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

10/10 Excellent

"We had a wonderful Labor Day Weekend at this property with three generations of the family. The house is clean, comfortable, and exactly as described, with a well-stocked kitchen and a fun game room. The dock is a short drive away and very easy to park next to on the side of the road. We came mostly to fish, and would love to come back and try again when it’s not so hot. Doesn’t hurt to bring some shade with you for the morning/midday, but we had a nice time swimming, kayaking, and fishing. The hosts were very communicative and eager to make sure we had a great stay. Would definitely come back."

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