Winchester Vacation Rentals
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Our top choices for Winchester vacation homes
1. Iconic Winchester home near Tims Ford State Park!
Iconic Winchester home near Tims Ford State Park!Winchester
The price is CA $110
CA $658 total
includes taxes & fees
Dec 2 - Dec 3
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 CA $147
CA $684 total
includes taxes & fees
Nov 15 - Nov 16
3. Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom Home
Luxury Lake Living- Pool , Fire Pit, Amenities 5 Bedroom HomeWinchester
The price is CA $299
CA $1,306 total
includes taxes & fees
Nov 15 - Nov 16
4. The Lakeside Getaway
The Lakeside GetawayWinchester
9.8 out of 10, Exceptional, (6 reviews)
"Incredible "
Jim C.
The price is CA $85
CA $611 total
includes taxes & fees
Nov 17 - Nov 18
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 CA $214
CA $3,194 total
includes taxes & fees
Nov 18 - Nov 19
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 CA $577
CA $1,255 total
includes taxes & fees
Nov 17 - Nov 18
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 CA $499
CA $1,066 total
includes taxes & fees
Nov 16 - Nov 17
8. 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 CA $91
CA $258 total
includes taxes & fees
Nov 15 - Nov 16
9. 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 CA $161
CA $631 total
includes taxes & fees
Nov 24 - Nov 25
10. 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)
"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!"
Missy M.
The price is CA $214
CA $267 total
includes taxes & fees
Nov 21 - Nov 22
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)"
Antonio M.
The price is CA $113
CA $420 total
includes taxes & fees
Nov 23 - Nov 24
12. 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)
"Nice place to stay. Close to the caverns where we saw a show. Property is very clean. Really nice stay."
Dawn
The price is CA $105
CA $304 total
includes taxes & fees
Nov 16 - Nov 17
13. 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.
The price is CA $238
CA $565 total
includes taxes & fees
Nov 16 - Nov 17
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."
Katherine B.
The price is CA $113
CA $401 total
includes taxes & fees
Nov 14 - Nov 15
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 CA $236
CA $744 total
includes taxes & fees
Nov 15 - Nov 16
16. 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 CA $105
CA $305 total
includes taxes & fees
Nov 23 - Nov 24
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!!"
Courtney C.
The price is CA $546
CA $1,177 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $141
CA $519 total
includes taxes & fees
Nov 15 - Nov 16
19. 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 CA $140
CA $272 total
includes taxes & fees
Dec 14 - Dec 15
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!"
katherine v.
The price is CA $435
CA $810 total
includes taxes & fees
Nov 22 - Nov 23
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
The Smokehouse Lodge and Cabins
10/10 Excellent
Find out more about Winchester
Winchester Vacation Homes information
Number of reviews | 391 |
|---|---|
Accommodation | 309 Vacation Homes |
Lowest Price | CA $258 |
Highest Price | CA $3,194 |
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