Holiday Homes in Winchester

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Winchester holiday homes

Fridge, microwave, oven, stovetop

Watch the sunrise with coffee and end the day with glowing Tennessee sunsets at this charming historic retreat just 5 minutes from Tims Ford Lake. Spacious, peaceful, and perfect for families or friends.

Watch the sunrise with coffee and end the day with glowing Tennessee sunsets at this charming historic retreat just 5 minutes from Tims Ford Lake. Spacious, peaceful, and perfect for families or friends.
Winchester
9.6 out of 10, Exceptional, (33 reviews)
"Clean, comfortable and 3 bathrooms are a blessing!"
United States
julie c.
The price is NZ$682
includes taxes & fees
29 June - 30 June
Watch the sunrise with coffee and end the day with glowing Tennessee sunsets at this charming historic retreat just 5 minutes from Tims Ford Lake. Spacious, peaceful, and perfect for families or friends.
Smart TV

Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient!

Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient!
Winchester
8.8 out of 10, Excellent, (19 reviews)
"Peaceful, relaxing and pet friendly great location!"
United States
Holly M.
The price is NZ$654
includes taxes & fees
29 June - 30 June
Gorgeous Renovated Home with Open Floor Plan and Large Lot, private but also convenient!
Property grounds

Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family

Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Winchester
10.0 out of 10, Exceptional, (35 reviews)
"Very nice! "
United States
Adam H.
The price is NZ$1,349
includes taxes & fees
9 June - 10 June
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Dining

The Lakefront Getaway

The Lakefront Getaway
Winchester
9.6 out of 10, Exceptional, (5 reviews)
"Incredible "
United States
Jim C.
The price is NZ$898
includes taxes & fees
1 June - 2 June
The Lakefront Getaway
Interior

Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp

Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
Winchester
10.0 out of 10, Exceptional, (6 reviews)
"We were only there for 1 night but the house was clean and comfortable and perfectly suited our needs. "
United States
Gwen K.
The price is NZ$1,267
includes taxes & fees
31 May - 1 June
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
Terrace/patio

Lakefront Lodge on Tims Ford Lake

Lakefront Lodge on Tims Ford Lake
Winchester
10.0 out of 10, Exceptional, (17 reviews)
"Awesome lake house!! A great retreat. Will come back someday we hope!! "
United States
Tara C.
The price is NZ$1,676
includes taxes & fees
7 June - 8 June
Lakefront Lodge on Tims Ford Lake
Outdoor dining

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
9.8 out of 10, Exceptional, (80 reviews)
"Excellent host as always...this is our 3rd year spending Thanksgiving at this property...excellent property, well furnished home and excellent host!"
United States
Amy F.
Amazing Tims Ford Lake Home - Built 2021 - Private covered dock - Hot Tub
Smart TV, fireplace

Water's Edge - Lakeside retreat

Water's Edge - Lakeside retreat
Winchester
Water's Edge - Lakeside retreat
Terrace/patio

The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort

The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
Winchester
10.0 out of 10, Exceptional, (8 reviews)
"Right on the water and next to the marina, great location! We stayed over Christmas week. We will be returning in the summer so we can enjoy the lake!"
United States
Andy D.
The price is NZ$1,964
includes taxes & fees
5 June - 6 June
The Love Shack - Waterside Cottage #1 with a DOCK on Tims Ford Lake at Twin Creeks Marina & Resort
Interior

Cove Sweet Cove - 3BR + 2BR Near the Caverns!

Cove Sweet Cove - 3BR + 2BR Near the Caverns!
Pelham
10.0 out of 10, Exceptional, (3 reviews)
"The cabin was just as advertised. It was clean and perfect location for the concert at the cavern. I would book again."
United States
Joanne G.
The price is NZ$387
includes taxes & fees
7 June - 8 June
Cove Sweet Cove - 3BR + 2BR Near the Caverns!
TV

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

Heavensent Tiny Home @ The Retreat at Water's Edge - Lake Views!
Tracy City
10.0 out of 10, Exceptional, (71 reviews)
"I took both of my sons to have a weekend away and we really enjoyed staying at the cabin. The fire pit was extremely relaxing. Great place to stay and the host is very nice. "
United States
Michael
The price is NZ$441
includes taxes & fees
2 June - 3 June
Heavensent Tiny Home @ The Retreat at Water's Edge - Lake Views!
Interior

High Point Getaway - Monteagle

High Point Getaway - Monteagle
Downtown Monteagle
9.4 out of 10, Exceptional, (21 reviews)
"Plenty of room for our family. "
United States
Keturah B.
The price is NZ$543
includes taxes & fees
1 June - 2 June
High Point Getaway - Monteagle
TV, fireplace

Hiker's Hangout Monteagle

Hiker's Hangout Monteagle
Monteagle
9.0 out of 10, Wonderful, (9 reviews)
"Super clean, great location and spacious! "
United States
Karen W.
The price is NZ$276
includes taxes & fees
31 May - 1 June
Hiker's Hangout Monteagle
Exterior

Foster’s Cabin 2 | 2 Minutes from Foster Falls

Foster’s Cabin 2 | 2 Minutes from Foster Falls
Sequatchie
10.0 out of 10, Exceptional, (2 reviews)
"Yes, my dog loved the place! "
United States
Christina G.
The price is NZ$311
includes taxes & fees
4 June - 5 June
Foster’s Cabin 2 | 2 Minutes from Foster Falls
Smart TV, fireplace

Walk to Deer Lick Falls | 12 Minutes to The Caverns | 18 Minutes to Coalmont OHV

Walk to Deer Lick Falls | 12 Minutes to The Caverns | 18 Minutes to Coalmont OHV
Monteagle
9.6 out of 10, Exceptional, (7 reviews)
The price is NZ$282
includes taxes & fees
31 May - 1 June
Walk to Deer Lick Falls | 12 Minutes to The Caverns | 18 Minutes to Coalmont OHV
Fridge, microwave, oven, stovetop

Time Well Wasted on the Lake

Time Well Wasted on the Lake
Tracy City
10.0 out of 10, Exceptional, (3 reviews)
"Great place, loved the screened in porch! Very clean, had everything we needed "
United States
John E.
The price is NZ$324
includes taxes & fees
10 June - 11 June
Time Well Wasted on the Lake
Microwave, oven, dishwasher, toaster

Nesthaven: A cozy boho-chic tiny home with a deck, fire pit, & nearby waterfall

Nesthaven: A cozy boho-chic tiny home with a deck, fire pit, & nearby waterfall
Monteagle
10.0 out of 10, Exceptional, (30 reviews)
"Everything was perfect quiet relaxing and super cute and had everything you needed definitely a must stay"
United States
Rosa F.
The price is NZ$398
includes taxes & fees
29 June - 30 June
Nesthaven: A cozy boho-chic tiny home with a deck, fire pit, & nearby waterfall
Property grounds

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

Creekside Tiny house in fantastic Monteagle! Quick hike to waterfall!
Monteagle
10.0 out of 10, Exceptional, (45 reviews)
"The place was amazing and very clean. "
United States
Kayla R.
The price is NZ$519
includes taxes & fees
4 June - 5 June
Creekside Tiny house in fantastic Monteagle! Quick hike to waterfall!
Fridge, microwave, oven, stovetop

Shea's Chalet - Cozy home in Monteagle, TN

Shea's Chalet - Cozy home in Monteagle, TN
Downtown Monteagle
9.6 out of 10, Exceptional, (21 reviews)
"Convenient location, house was well stocked, clean and the beds were extremely comfortable."
United States
Buck J.
The price is NZ$414
includes taxes & fees
31 May - 1 June
Shea's Chalet - Cozy home in Monteagle, TN
Terrace/patio

Caverns,Sewanee,Waterfall,Hikes : Tiny Basecamp

Caverns,Sewanee,Waterfall,Hikes : Tiny Basecamp
Monteagle
10.0 out of 10, Exceptional, (69 reviews)
"This cabin was the perfect weekend getaway for our family of 5. The host had excellent communication during our stay. Highly recommend! "
United States
Kelsey
The price is NZ$351
includes taxes & fees
23 June - 24 June
Caverns,Sewanee,Waterfall,Hikes : Tiny Basecamp
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

Best Western Inn

Best Western Inn

4/10 Poor
"We thought we were getting the room with a stove and when we got our room there was an open spot for the stove and no stove. The picture was deceiving. It showed that there was a stove in the room the room looked really nice really nice. So we were going to barbecue also and they said they had a barbecue well found out they didn’t have a barbecue so I didn’t get to go and barbecue my steaks I brought. The pictures were really deceiving, but we made the best of it."
troy 2-night trip
Posted 1 day ago
Best Western Inn

Find out more about Winchester

Winchester Holiday Homes information

Number of reviews
382
Accommodation
318 Holiday Homes
Lowest Price
NZ$276
Highest Price
NZ$1,964