Search Vacation Homes in Winchester

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Compare 260 Vacation Homes in Winchester with updated reviews, rates, and availability.

Exterior
Tennessee Getaway (near Jack Daniel’s and Nearest Green distilleries)
10.0 out of 10, Exceptional, (28)
"Only stayed one night as we were in to pick some barrels of whiskey at Jack Daniel’s Close to the distillery and was amazed at how nice the home is. It has been updated and is much nicer than we expected. Would stay here again!"
The price is $155
$320 total
includes taxes & fees
May 19 - May 20
Tennessee Getaway (near Jack Daniel’s and Nearest Green distilleries)
Lake
3 bedroom 1 bath vacation home, sleeps 6 people.
10.0 out of 10, Exceptional, (144)
"Great place would stay again!!"
The price is $175
$322 total
includes taxes & fees
May 19 - May 20
3 bedroom 1 bath vacation home, sleeps 6 people.
Exterior
Rooster's Roost of Bells Cove
10.0 out of 10, Exceptional, (10)
"Wish we had been in the area for a longer stay. The house was decorated beautifully. Loved the style. Our puppy loved running around the yard. She is used to the space at home. Makes for a tired puppy at bedtime! Would definitely stay again if in the area."
The price is $116
$276 total
includes taxes & fees
May 19 - May 20
Rooster's Roost of Bells Cove
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Property grounds
NEW! ON A WATERFALL! Stunning Views, Huge Bluffs, Waterfront, Deck, 13 acres!
10.0 out of 10, Exceptional, (3)
"This home and its grounds are a slice of paradise! The view from the deck is beautiful and so peaceful--2 waterfalls! We had our coffee and breakfast on the deck every morning and ate several dinners there too. The kitchen has new appliances and is stocked with everything, including spices, needed to cook great meals. There is also a nice gas grill and a park grill (for people like my husband who love old school charcoal grilling). The bed in the master was so comfortable, with soft, high...
NEW! ON A WATERFALL! Stunning Views, Huge Bluffs, Waterfront, Deck, 13 acres!
Property grounds
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK
10.0 out of 10, Exceptional, (16)
"We stayed here for a staff retreat and comfortably had 10 people stay. It's spacious, beautiful, and clean, and the layout is awesome. There's a grocery store nearby for quick runs and close to pickleball courts and hiking. It's right on the lake with an awesome back yard and deck to make mornings and evenings extra great."
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK
Fridge, microwave, oven, stovetop
Country Charmer near lake new hot tub handicap accessible Extended stay
10.0 out of 10, Exceptional, (4)
"We really enjoyed our stay. The location was perfect for our stay. The property was beautiful. The game room was a plus for my children. The extras special touches the host left were much appreciated."
Country Charmer near lake new hot tub handicap accessible Extended stay
Smart TV, fireplace
Lakeshore Modern Brand new for 2023! Lake front with platform dock and 2 kayaks
10.0 out of 10, Exceptional, (7)
"What a great weekend! This group of 6 girls, work together and live 30 mins or less to Winchester. We wanted to spend time with each other and have fun! That’s exactly what we did! AMAZING HOUSE!!!! Everything you need!!!! I won’t lie….snow storm headed to Tennessee….I wish I could’ve stayed all week and watch the snow. Absolutely breathtaking house! A+. Tara is an amazing host….we communicated about several things. She was always on it!!! Thank you Tara for a wonderful experience. People...
Lakeshore Modern Brand new for 2023! Lake front with platform dock and 2 kayaks
Fridge, microwave, oven, stovetop
Mountain Memories to provide a cozy retreat on your vacation!
10.0 out of 10, Exceptional, (2)
"We loved our stay at Moutain Memories. The rooms are spacious, the house was so neat and everything was new! We enjoyed how close it was to Sewanee and the little things provided, such as a Keurig, body wash, shampoo, and conditioner. The home was tastefully decorated and can easily accommodate 4-6 people. We had plenty of room and enjoyed the kitchen and living area. There are a few things that might need to be added such as a few more end tables in the living room, some coasters to set drinks...
The price is $90
$213 total
includes taxes & fees
May 20 - May 21
Mountain Memories to provide a cozy retreat on your vacation!
Outdoor dining
Lakefront property, spacious family retreat with private dock, hot tub & kayak
10.0 out of 10, Exceptional, (34)
"The home is spacious, and was very clean. We traveled with 2 adults and 3 teens. There was plently of cooking gear in the kitchen for making big meals, which we always do. The beds were comfortbale- there are so many beds in this house I lost count! Two big couches, lots of room for everyone to spread out. A wonderful screened in porch area. Upper and lower level decks were beautiful. Plenty of hot water. Some big flatheads in that cove, fishing right off the dock. They like garlic and red...
Lakefront property, spacious family retreat with private dock, hot tub & kayak
Exterior
The Sewanee House: Serene Oasis 5 minutes from Campus
10.0 out of 10, Exceptional, (21)
"10 of us headed to unknown terrirtory--stayed in Sewanee to attend a concert (Irish band "Altan") at The Caverns. We wanted a place we could all be together (ha, we travel in a herd) and wanted a place where we would not disturb anyone as we love our music, competitive games (ha). This place was PERFECT! Extra clean, plenty of room, clear on what we needed to do on arrival/departure. Kathryn, property manager, was an awesome communicator, and appreciated her efforts in finding places to eat--we...
The Sewanee House: Serene Oasis 5 minutes from Campus
Fridge, microwave, oven, stovetop
Muse at Monteagle at The Retreat at Deer Lick Falls
10.0 out of 10, Exceptional, (23)
"We went to the Caverns for a show and stayed over night but wish we had more time to enjoy this sweet house!"
The price is $100
$272 total
includes taxes & fees
May 19 - May 20
Muse at Monteagle at The Retreat at Deer Lick Falls
Property grounds
Tims Ford Lake Retreat - The Got-Away
10.0 out of 10, Exceptional, (10)
"Visited a longtime friend who lost her husband during covid, Facilities were absolutely perfect for our group of retired folks. Beautiful area. Would definitely consider coming back."
Tims Ford Lake Retreat - The Got-Away
Tims Ford Lake Access Detached Home, Lynchburg, TN
10.0 out of 10, Exceptional, (231)
"Wanted to get away & have relaxing weekend. This property was perfect. Nestled away from all the hustle & bustle of everyday life. Ginger was amazing & helpful with everything. We even had a visit from Daisey☺️❤️"
Tims Ford Lake Access Detached Home, Lynchburg, TN
Fridge, microwave, oven, stovetop
Minutes from Monteagle Parks and Restaurants!
10.0 out of 10, Exceptional, (20)
"We have a great time. We were located near so many hiking trails. The house was so clean and had a great yard for our kids to play in. We loved putting puzzles together in the kitchen and cooking meals. We look forward to staying here again."
The price is $224
$498 total
includes taxes & fees
May 19 - May 20
Minutes from Monteagle Parks and Restaurants!
Property grounds
Lak Haus: Resort-Style Home on Tims Ford Lake!
10.0 out of 10, Exceptional, (42)
"Great little get away in the beautiful Leatherwood community."
Lak Haus: Resort-Style Home on Tims Ford Lake!
2 bedrooms, desk, free WiFi, bed sheets
Cozy Renovated Bungalow Steps Away from Hiking Trails, Nature and Stellar Sunset
10.0 out of 10, Exceptional, (5)
"Surprisingly comfortable for a group of 4 friends. The kitchen/dining/living room area is spacious and cozy and the bedrooms are super comfortable. Definitely recommend if you find yourself in this rural area in need of great accommodations."
The price is $150
$333 total
includes taxes & fees
May 19 - May 20
Cozy Renovated Bungalow Steps Away from Hiking Trails, Nature and Stellar Sunset
Interior
Weblon's Retreat - Incredible Bluff View and Peaceful Woods
10.0 out of 10, Exceptional, (5)
"Great place for large family trip"
Weblon's Retreat - Incredible Bluff View and Peaceful Woods
3 bedrooms, free WiFi, bed sheets
Cozy basecamp minutes from waterfalls, hiking and climbing
10.0 out of 10, Exceptional, (4)
"Very wonderful!"
The price is $124
$204 total
includes taxes & fees
May 20 - May 21
Cozy basecamp minutes from waterfalls, hiking and climbing
Fridge, microwave, oven, stovetop
New June Openings! Spacious Lakefront Getaway with Dock on Tims Ford Lake!
10.0 out of 10, Exceptional, (35)
"Beautiful place! We enjoyed our stay!"
New June Openings! Spacious Lakefront Getaway with Dock on Tims Ford Lake!
Outdoor dining
Family friendly lake front home with private dock in a cove
9.8 out of 10, Exceptional, (16)
"Plenty of room for our family get together. Way larger than pictures show. Would definitely book again next time!!!"
Family friendly lake front home with private dock in a cove
Don't see what you're looking for?
See all available properties in Winchester
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.

Other property types in Winchester

Property grounds
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK
10.0 out of 10, Exceptional, (16)
"We stayed here for a staff retreat and comfortably had 10 people stay. It's spacious, beautiful, and clean, and the layout is awesome. There's a grocery store nearby for quick runs and close to pickleball courts and hiking. It's right on the lake with an awesome back yard and deck to make mornings and evenings extra great."
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK
Interior
Luxurious Waterfront Oasis on Tims Ford Lake!
10.0 out of 10, Exceptional, (37)
"We have stayed at quite a few homes and this was by far one of our favorites. Linda was an amazing host and went above and beyond to make our stay memorable."
Luxurious Waterfront Oasis on Tims Ford Lake!
Property grounds
Million Dollar Views: Lakefront, Dock, Kayaks+More
10.0 out of 10, Exceptional, (30)
"We had an amazing stay. The property was perfect for our family. Even though the water was cold, the younger bunch enjoyed the kayaks. Thanks for a great time with family."
The price is $249
$684 total
includes taxes & fees
May 22 - May 23
Million Dollar Views: Lakefront, Dock, Kayaks+More
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.

Winchester Vacation Homes information

Number of reviews
616
Accommodation
260 Vacation Homes
Lowest Price
$89
Highest Price
$588

Recent reviews of Winchester hotels
Expedia verified reviews

Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks

5/5 Excellent
Excellent Trip! - Visited local distilleries
"We had a great time at this house. Loved the log cabin feel, it was very cozy and with great amenities. Great communication from the owner. Visited 3 local distilleries, what a fun trip! Would absolutely come back."
A verified traveler stayed at Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks
Posted 10 days ago
Rustic Cabin, Dock, Hot Tub, Firepit, Kayaks