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Our top choices for Winchester holiday homes
1. Iconic Winchester home near Tims Ford State Park!
Iconic Winchester home near Tims Ford State Park!Winchester
The price is HK$894
HK$3,799 total
includes taxes & fees
22 Nov - 23 Nov
2. *NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub
*NEW* Shoreline Escape: Lakefront Retreat w/ Hot TubWinchester
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."
Vonda R.
The price is HK$949
HK$3,896 total
includes taxes & fees
9 Dec - 10 Dec
3. Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom HomeWinchester
The price is HK$1,663
HK$7,202 total
includes taxes & fees
10 Nov - 11 Nov
4. The Lakefront Getaway
The Lakefront GetawayWinchester
9.8 out of 10, Exceptional, (6 reviews)
"Incredible "
Jim C.
The price is HK$467
HK$3,360 total
includes taxes & fees
10 Nov - 11 Nov
5. Luxurious Lakefront Home- Marina, Boats, and Kayaks!
Luxurious Lakefront Home- Marina, Boats, and Kayaks!Winchester
10.0 out of 10, Exceptional, (1 review)
"We really enjoyed our stay. The home was great! Everything you need. Love the location. Close to Winchester and the lake. Highly recommend. Already planning to stay there again."
Gary W.
The price is HK$933
HK$17,240 total
includes taxes & fees
12 Nov - 13 Nov
6. Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot TubWinchester
10.0 out of 10, Exceptional, (83 reviews)
"We had a great time! "
Cindy O.
The price is HK$3,175
HK$6,903 total
includes taxes & fees
10 Nov - 11 Nov
7. Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12Winchester
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."
Timothy W.
The price is HK$2,744
HK$5,867 total
includes taxes & fees
10 Nov - 11 Nov
8. Treetop Mountain Retreat Near Sewanee | Sleeps 6
Treetop Mountain Retreat Near Sewanee | Sleeps 6Sewanee
10.0 out of 10, Exceptional, (2 reviews)
"Great proximity to the college with ample parking."
Lisa C.
The price is HK$886
HK$3,454 total
includes taxes & fees
10 Nov - 11 Nov
9. Spacious private guesthouse within minutes of Tims Ford Lake and Woods Reservoir
Spacious private guesthouse within minutes of Tims Ford Lake and Woods ReservoirTullahoma
9.6 out of 10, Exceptional, (8 reviews)
"Very clean and convenient. The host was was very helpful."
George G.
10. Whiskey Trails Cottage
Whiskey Trails CottageTullahoma
10.0 out of 10, Exceptional, (26 reviews)
"Great place to stay. Had everything we needed. Great location."
Jennifer T.
The price is HK$500
HK$1,411 total
includes taxes & fees
15 Nov - 16 Nov
11. Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns
Partin's Perch | Indoor Private Sauna | 9 Min from The CavernsPelham
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!"
Andrea
The price is HK$579
HK$1,672 total
includes taxes & fees
10 Dec - 11 Dec
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)"
Antonio M.
The price is HK$624
HK$2,214 total
includes taxes & fees
10 Nov - 11 Nov
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!!"
Courtney C.
The price is HK$2,999
HK$6,470 total
includes taxes & fees
10 Nov - 11 Nov
14. Tims Ford Lake Home: Screened Porch, EV
Tims Ford Lake Home: Screened Porch, EVTullahoma
10.0 out of 10, Exceptional, (6 reviews)
"Excellent stay, beautiful property"
cassie l.
15. Forest Retreat: Poolside Bliss Close to Campus
Forest Retreat: Poolside Bliss Close to CampusSewanee
10.0 out of 10, Exceptional, (14 reviews)
"Excellent communication - perfect location! GREAT STAY! "
Sally B.
The price is HK$1,309
HK$4,085 total
includes taxes & fees
10 Nov - 11 Nov
16. Cove Sweet Cove - 3BR + 2BR Near the Caverns!
Cove Sweet Cove - 3BR + 2BR Near the Caverns!Pelham
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful place. Easy drive to the Caverns for music."
Katherine B.
The price is HK$624
HK$2,142 total
includes taxes & fees
10 Nov - 11 Nov
17. 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, (37 reviews)
"wonderful place to stay right on Sewanee's campus!"
katherine v.
The price is HK$2,392
HK$4,453 total
includes taxes & fees
13 Nov - 14 Nov
18. Lakes, Whiskey & More! Charming Home in Tullahoma
Lakes, Whiskey & More! Charming Home in TullahomaTullahoma
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."
Wendy D.
The price is HK$776
HK$2,837 total
includes taxes & fees
7 Dec - 8 Dec
19. Tiny Haven at the Retreat
Tiny Haven at the RetreatMonteagle
9.4 out of 10, Exceptional, (23 reviews)
"We loved it."
Todd
The price is HK$579
HK$1,633 total
includes taxes & fees
10 Nov - 11 Nov
20. Caverns•Sewanee•Waterfalls•Hikes• Tiny Basecamp
Caverns•Sewanee•Waterfalls•Hikes• Tiny BasecampMonteagle
10.0 out of 10, Exceptional, (88 reviews)
"We enjoyed our stay at Tiny Mojo. It was conveniently located to the Caverns, Sewanee, and lots of hiking. The host was very helpful and the house was very clean and comfortable."
Kelley P.
The price is HK$855
HK$1,607 total
includes taxes & fees
16 Nov - 17 Nov
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.
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.
