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 $112
CA $658 total
includes taxes & fees
Nov 15 - Nov 16
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 $177
CA $719 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 $298
CA $1,300 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 $84
CA $608 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 $213
CA $3,176 total
includes taxes & fees
Nov 29 - Nov 30
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 $575
CA $1,249 total
includes taxes & fees
Nov 12 - Nov 13
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 $494
CA $1,057 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 $90
CA $257 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 $160
CA $628 total
includes taxes & fees
Nov 12 - Nov 13
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 $213
CA $266 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 $418 total
includes taxes & fees
Nov 16 - Nov 17
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)
"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 CA $104
CA $303 total
includes taxes & fees
Dec 1 - Dec 2
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 $237
CA $563 total
includes taxes & fees
Nov 15 - Nov 16
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 $112
CA $397 total
includes taxes & fees
Nov 23 - Nov 24
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 $235
CA $740 total
includes taxes & fees
Nov 12 - Nov 13
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 $303 total
includes taxes & fees
Nov 16 - Nov 17
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 $543
CA $1,171 total
includes taxes & fees
Nov 12 - Nov 13
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 $140
CA $516 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 $275 total
includes taxes & fees
Nov 16 - Nov 17
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 $433
CA $806 total
includes taxes & fees
Nov 15 - Nov 16
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
La Quinta Inn & Suites by Wyndham Manchester / Arnold AFB
10/10 Excellent
Find out more about Winchester
Winchester Vacation Homes information
Number of reviews | 391 |
|---|---|
Accommodation | 309 Vacation Homes |
Lowest Price | CA $257 |
Highest Price | CA $3,176 |
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