Winchester, TN Vacation Homes from AED 218

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Our top choices for Winchester vacation homes

A modern living room with a blue sofa, a staircase, a kitchen, and a fireplace.

1. Iconic Winchester home near Tims Ford State Park!

Winchester

AED 1,599 total

includes taxes & fees

9 Nov - 10 Nov

A kitchen with a coffee machine, a sink, and a window with curtains.

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

Winchester

Vonda R.

AED 1,705 total

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

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

Winchester

AED 3,365 total

includes taxes & fees

10 Nov - 11 Nov

4. The Lakeside Getaway

Winchester

Jim C.

AED 1,574 total

includes taxes & fees

10 Nov - 11 Nov

5. Luxurious Lakefront Home- Marina, Boats, and Kayaks!

Winchester

Gary W.

AED 8,582 total

includes taxes & fees

12 Nov - 13 Nov

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

Winchester

Timothy W.

AED 2,635 total

includes taxes & fees

8 Nov - 9 Nov

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

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

Winchester

Cindy O.

AED 3,234 total

includes taxes & fees

8 Nov - 9 Nov

A modern dining area with a wooden table, bar stools, a TV, and a fireplace.

8. Whiskey Trails Cottage

Tullahoma

Jennifer T.

AED 728 total

includes taxes & fees

8 Nov - 9 Nov

A rustic cabin surrounded by dense forest.

9. Treetop Mountain Retreat Near Sewanee | Sleeps 6

Sewanee

Lisa C.

AED 1,611 total

includes taxes & fees

8 Nov - 9 Nov

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

Tullahoma

George G.

AED 685 total

includes taxes & fees

21 Nov - 22 Nov

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

Pelham

Andrea

AED 787 total

includes taxes & fees

9 Nov - 10 Nov

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!

Pelham

Antonio M.

AED 1,052 total

includes taxes & fees

10 Nov - 11 Nov

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

Tullahoma

cassie l.

AED 1,453 total

includes taxes & fees

9 Nov - 10 Nov

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.

Estill Springs

Courtney C.

AED 3,031 total

includes taxes & fees

9 Nov - 10 Nov

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!

Pelham

Katherine B.

AED 1,000 total

includes taxes & fees

8 Nov - 9 Nov

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

16. Forest Retreat: Poolside Bliss Close to Campus

Sewanee

Sally B.

AED 1,909 total

includes taxes & fees

9 Nov - 10 Nov

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

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

Monteagle

Jennifer M.

AED 760 total

includes taxes & fees

8 Dec - 9 Dec

A modern kitchen with white cabinets, a black refrigerator, and a dining area with two black chairs and a white fluffy rug.

18. Tiny Haven at the Retreat

Monteagle

Todd

AED 765 total

includes taxes & fees

9 Nov - 10 Nov

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.

Sewanee

katherine v.

AED 2,086 total

includes taxes & fees

11 Nov - 12 Nov

A living room with two sofas, a coffee table, a ceiling fan, a flat-screen TV, and a window with curtains.

20. Lakes, Whiskey & More! Charming Home in Tullahoma

Tullahoma

Wendy D.

AED 1,329 total

includes taxes & fees

15 Nov - 16 Nov

View all properties

Learn more about Winchester

Nestled between rolling hills, this charming town offers visitors the crystal-clear waters of Tims Ford Lake for boating and fishing. Explore downtown's historic courthouse square where local shops serve up Southern hospitality alongside the famous Winchester Swamp Festival each September.

See all hotels in Winchester

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

Top reviews in Winchester

Best Western Inn

Winchester

10/10 Excellent

Cindy

A stone building with a covered patio area, stone pillars, and outdoor seating.

The Sewanee Inn

Sewanee

10/10 Excellent

I had the pleasure of staying at the Sewanee Inn with 3 friends, as our daughters stayed on campus overnight and attended a class the next morning. We had a beautiful evening sitting on the back patio by the golf course, with heat lamps that resembled torches adding to the ambiance. The next morning, we enjoyed a delicious breakfast in the dining room with a friendly, accomodating staff and delicious food! I LOVE it that the Inn has bicycles for guests to use , as the "Green lookout" as well...

Michelle

A modern hotel building with a sign reading "LivSmart Studios by Hilton".

LivSmart Studios by Hilton Tullahoma

Tullahoma

10/10 Excellent

Michael

A hotel with a brick facade, a covered entrance, and a parking lot.

Holiday Inn Express Hotel & Suites Tullahoma by IHG

Tullahoma

10/10 Excellent

Penny

A spacious room with a stone fireplace, a flat-screen TV mounted above it, and a green upholstered sofa.

Quality Inn Monteagle

Downtown Monteagle

10/10 Excellent

Darci

A two-story house with a front porch, stone steps, and two lion statues.

Tolley House

Lynchburg

10/10 Excellent

Ashley

A hotel entrance with a stone facade, large glass doors, and a well-lit outdoor area with plants and seating.

Lx Hotel, SureStay Collection by Best Western, Manchester, near Arnold AFB

Manchester

10/10 Excellent

Very clean and spacious room, comfortable bed, thick towels. Communication from the owners was excellent prior to and during our stay. Called in our breakfast order the night before, and were then served our hot homemade breakfast in the lobby dining area in the morning. Would definitely recommend staying at this property again. Extra thoughtful owners also provided a complimentary happy hour and snack in the evening.

Carole