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Compare 317 Vacation Homes in Winchester with updated reviews, rates, and availability.

Mountain Memories to provide a cozy retreat on your vacation!

9.8 out of 10, Exceptional, (23)
"Lovely home in a small, very quiet neighborhood. Centrally located to many attractions and activities. Will stay here again when we're back in the area."
The price is SAR 338
SAR 796 total
includes taxes & fees
2 Jun - 3 Jun
Mountain Memories to provide a cozy retreat on your vacation!

Trillium Ranch located Central to Campus 2 blocks from All Saints!

9.6 out of 10, Exceptional, (35)
"Great location, comfortable accomodations."
Trillium Ranch located Central to Campus 2 blocks from All Saints!

Dock, Water Views, Kayaks, Fire Pit, Game Room

10.0 out of 10, Exceptional, (16)
"Beautiful home with everything we needed for our stay! The kids loved the game/bunk room and golf cart rides to the awesome dock. We enjoyed it so much and felt right at home!"
Dock, Water Views, Kayaks, Fire Pit, Game Room

Mountain Point of View Cottage

9.6 out of 10, Exceptional, (19)
"Our stay was perfect , it was very relaxing and very beautiful. Thank you for a great stay !"
The price is SAR 300
SAR 729 total
includes taxes & fees
29 May - 30 May
Mountain Point of View Cottage

Gorgeous Renovated Home with Open Floor Plan and Large Lot

9.2 out of 10, Wonderful, (11)
"We enjoyed the cottages roomie interior and comfortable beds. We saw a deer enjoyed walking the dog around the property and had a peaceful night sleep."
The price is SAR 439
SAR 1,293 total
includes taxes & fees
3 Jun - 4 Jun
Gorgeous Renovated Home with Open Floor Plan and Large Lot

Heavensent Tiny Home @ The Retreat at Water's Edge - Lake Views!

10.0 out of 10, Exceptional, (54)
"We live in Nashville so were looking for a close & quiet location. This one was just what we needed!"
The price is SAR 371
SAR 984 total
includes taxes & fees
29 May - 30 May
Heavensent Tiny Home @ The Retreat at Water's Edge - Lake Views!

Caverns,Sewanee,Hikes,Waterfalls: Tiny Basecamp

10.0 out of 10, Exceptional, (38)
"Management was super in touch and very accommodating. Place was clean and very well decorated and stocked. You can tell they care."
The price is SAR 420
SAR 814 total
includes taxes & fees
4 Jun - 5 Jun
Caverns,Sewanee,Hikes,Waterfalls: Tiny Basecamp

Charming 125 Year Old Sewanee Home on Campus- Walk Everywhere!

9.6 out of 10, Exceptional, (124)
"We had a great stay. Great location for getting around campus."
Charming 125 Year Old Sewanee Home on Campus- Walk Everywhere!

Waterfront•Hot Tub•Arcade•Kayaks•Fishing•Patio•Golf•Sweetens Cove Lodge

10.0 out of 10, Exceptional, (1)
"The house is awesome! The location is beautiful and close to Chattanooga. Lots of tourist activities nearby. The house has a great outside area with outdoor seating, big screen tv, and a hot tub near the beautiful relaxing creek. Inside is spacious with a spa like bathroom. The kitchen had several items in the refrigerator and a coffee bar area. The owners were wonderful to deal with. I highly recommend this rental!"
Waterfront•Hot Tub•Arcade•Kayaks•Fishing•Patio•Golf•Sweetens Cove Lodge

Charming Tullahoma Stay w/ Great Walkable Location

8.6 out of 10, Excellent, (7)
"It was nice."
Charming Tullahoma Stay w/ Great Walkable Location

Sunset Cove- Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc

9.8 out of 10, Exceptional, (19)
"Great location. Very clean, well equipped, good communication with managers."
Sunset Cove- Lake Home, Dock, Fire Pit, Hot Tub, Game Room, Etc

Eagle's Point - Sleeps 12 with an incredible view!

9.8 out of 10, Exceptional, (102)
"very comfortable and clean property. wonderful setting. Host Gary was very accommodating and quick to respond to any inquiries. had a great time. would recommend."
Eagle's Point - Sleeps 12 with an incredible view!

Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

10.0 out of 10, Exceptional, (48)
"We had a great time at Barefoot Bay!"
Waterfront Oasis On Tims Ford Lake: Pool/Kayak!

Creekside Tiny house in fantastic Monteagle! Quick hike to waterfall!

10.0 out of 10, Exceptional, (7)
"Loved the home and creek. "
The price is SAR 581
SAR 1,217 total
includes taxes & fees
29 May - 30 May
Creekside Tiny house in fantastic Monteagle! Quick hike to waterfall!

Tennessee Getaway (near Jack Daniel’s and Nearest Green distilleries)

10.0 out of 10, Exceptional, (47)
"Cute little house with all the amenities centrally located to all the things we wanted to do. Would definitely stay here again. "
The price is SAR 581
SAR 1,193 total
includes taxes & fees
29 May - 30 May
Tennessee Getaway (near Jack Daniel’s and Nearest Green distilleries)

Gather at Tims Ford Lake

9.6 out of 10, Exceptional, (17)
"Beautiful house on a beautiful lake. House was clean and amenities were as advertised. Thank you for a great weekend getaway."
The price is SAR 2,063
SAR 3,916 total
includes taxes & fees
2 Jun - 3 Jun
Gather at Tims Ford Lake

Best Day Yet! Spacious 5-bedroom house in Twin Creeks Village

Best Day Yet! Spacious 5-bedroom house in Twin Creeks Village

Mid-Century Estate - Home/Loft - Hot Tub/Game Room

10.0 out of 10, Exceptional, (5)
"My group really enjoyed our stay. It was perfect for our trip."
The price is SAR 1,031
SAR 2,419 total
includes taxes & fees
8 Jun - 9 Jun
Mid-Century Estate - Home/Loft - Hot Tub/Game Room

Whiskey Trails Cottage

10.0 out of 10, Exceptional, (6)
"The host “The Good Family” is amazing. Very communicative, through out our stay. "
Whiskey Trails Cottage

Whispering Woods Tracy City

2.0 star property
9.6 out of 10, Exceptional, (7)
"Great little place to stay just what we needed. Having little fire pit area was very nice. "
The price is SAR 338
SAR 1,067 total
includes taxes & fees
29 May - 30 May
Whispering Woods Tracy City
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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Other property types in Winchester

Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak

2.0 star property
10.0 out of 10, Exceptional, (6)
"We booked this place for my grandmothers 80th birthday trip. The whole family came together. This place was truly awesome. So clean, so many things to do and fit all of us so nice. We will definitely be back. "
Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak

"The Hawk Nest" cabin on Tims Ford Lake

9.4 out of 10, Exceptional, (14)
"Just spent the night there to relax and get away got a little bit of work done and was able to relax"
The price is SAR 859
SAR 1,729 total
includes taxes & fees
29 May - 30 May
"The Hawk Nest" cabin on Tims Ford Lake

Reflection Bay-Dock, Hot Tub, Kayaks

10.0 out of 10, Exceptional, (6)
"Place was great"
Reflection Bay-Dock, Hot Tub, Kayaks
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.