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

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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 £332
includes taxes & fees
30 Nov - 1 Dec
Iconic Winchester home near Tims Ford State Park!

2. *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 £357
includes taxes & fees
15 Nov - 16 Nov
*NEW* Shoreline Escape: Lakefront Retreat w/ Hot Tub

3. 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 £690
includes taxes & fees
24 Nov - 25 Nov
Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home

4. The Lakefront Getaway

The Lakefront Getaway
Winchester
9.8 out of 10, Exceptional, (6 reviews)
"Incredible "
United States
Jim C.
The price is £317
includes taxes & fees
17 Nov - 18 Nov
The Lakefront Getaway

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."
United States
Gary W.
The price is £1,694
includes taxes & fees
17 Nov - 18 Nov
Luxurious Lakefront Home- Marina, Boats, and Kayaks!

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 £663
includes taxes & fees
15 Nov - 16 Nov
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub

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 £564
includes taxes & fees
15 Nov - 16 Nov
Lakeview Retreat, Covered Boat Slip, Swim Ladder, Sleeps 12

8. 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 £138
includes taxes & fees
15 Nov - 16 Nov
Whiskey Trails Cottage

9. 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 £330
includes taxes & fees
15 Nov - 16 Nov
Treetop Mountain Retreat Near Sewanee | Sleeps 6

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)
"The place was super cute and clean. It was perfect for a little weekend getaway. The wifi password listed on the listing is wrong but the owner was very punctual in answering my questions about it. Overall, would stay here again!"
United States
Missy M.
The price is £143
includes taxes & fees
21 Nov - 22 Nov
Spacious private guesthouse within minutes of Tims Ford Lake and Woods Reservoir

11. 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, (40 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 £221
includes taxes & fees
30 Nov - 1 Dec
Rooster's Roost of Bells Cove - 15 Minutes from the Caverns!

12. 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)
"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 £162
includes taxes & fees
6 Dec - 7 Dec
Partin's Perch | Indoor Private Sauna | 9 Min from The Caverns

13. 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 £290
includes taxes & fees
16 Nov - 17 Nov
Tims Ford Lake Home: Screened Porch, EV

14. 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."
United States
Katherine B.
The price is £214
includes taxes & fees
14 Dec - 15 Dec
Cove Sweet Cove - 3BR + 2BR Near the Caverns!

15. Forest Retreat: Poolside Bliss Close to Campus

Forest Retreat: Poolside Bliss Close to Campus
Sewanee
10.0 out of 10, Exceptional, (14 reviews)
"Excellent communication - perfect location! GREAT STAY! "
United States
Sally B.
The price is £390
includes taxes & fees
15 Nov - 16 Nov
Forest Retreat: Poolside Bliss Close to Campus

16. 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
Tiny Haven at the Retreat

17. 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 £621
includes taxes & fees
15 Nov - 16 Nov
Lake Life 4 Bedroom, 3 Bath, Sleeps 12.

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 £272
includes taxes & fees
15 Nov - 16 Nov
Lakes, Whiskey & More! Charming Home in Tullahoma

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

Caverns•Sewanee•Waterfalls•Hikes• Tiny Basecamp
Monteagle
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."
United States
Kelley P.
The price is £147
includes taxes & fees
14 Dec - 15 Dec
Caverns•Sewanee•Waterfalls•Hikes• Tiny Basecamp

20. 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!"
United States
katherine v.
The price is £413
includes taxes & fees
19 Nov - 20 Nov
On the University of the South campus, Sewanee, TN.
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

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
391
Accommodation
313 Holiday Homes
Lowest Price
£138
Highest Price
£1,694