Vacation Rentals in Winchester, TN

PRICE PER NIGHT

ACCOMMODATION TYPES

Top-Rated Vacation Rentals in Winchester, TN

Book a vacation rental in Winchester that has the highest visitor rating. Here are 6 of the best vacation rentals in Winchester.
LAKESIDE at Twin Creeks- 2 King Primary En-Suites + 7 minute walk to marina!
10

Excellent

·
Winchester
·
4 br
·
Sleeps 14
·
Dishwasher · Oven · Wifi ·
From
$264/night
Check availability
Property
House · 4 Beds · 4 baths
Amenities
Dishwasher
Oven
Wifi
Air Conditioning
Pool
Swimming Pool
Furnished
Fitness Center
Other spaces
Kitchen, Workspace
NewBuild Lakehouse 4BR4BA 2Kitchen DoubleDeck SwimPool BoatRamp Family Vacation
10

Excellent

·
Winchester
·
4 br
·
Sleeps 10
·
Pool · Lake · Fireplace ·
From
$215/night
Check availability
Property
House · 4 Beds · 4 baths
Amenities
Pool
Lake
Fireplace
Air Conditioning
In Unit Laundry
Garage Parking
Furnished
Waterfront
Other spaces
Kitchen, Workspace
Spacious Lakeside Home, Pet-Friendly w/Dock & Boatslip
10

Excellent

·
Winchester
·
3 br
·
Sleeps 12
·
Furnished · Air Conditioning · Outdoor Space ·
From
$377/night
Check availability
Property
House · 3 Beds · 6 baths
Amenities
Furnished
Air Conditioning
In Unit Laundry
Waterfront
Garage Parking
Wifi
Dishwasher
Oven
Other spaces
Workspace, Kitchen
Deluxe 5BR Lakefront Home - 2 Docks & Boat Ramp
10

Excellent

·
Winchester
·
5 br
·
Sleeps 19
·
Hot Tub · In Unit Laundry · Kitchen ·
From
$775/night
Check availability
Property
House · 5 Beds · 4 baths
Amenities
Hot Tub
In Unit Laundry
Fireplace
Wifi
Oven
Air Conditioning
Ceiling Fan
Waterfront
Other spaces
Kitchen
Historic Hideaway On the Square #9.
10

Excellent

·
Winchester
·
2 br
·
Sleeps 6
·
In Unit Laundry · Wifi · Kitchen ·
From
$125/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
In Unit Laundry
Wifi
Furnished
Air Conditioning
Other spaces
Kitchen
Modern Luxury Retreat: Walk to Tims Ford Lake!
10

Excellent

·
Winchester
·
4 br
·
Sleeps 10
·
Assigned Parking · Cable · Pool ·
From
$234/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Assigned Parking
Cable
Pool
Wifi
Central Heat
Lake
Walk In Closets
Air Conditioning
Other spaces
Workspace, Kitchen, Garden

Budget-Friendly Vacation Rentals in Winchester, TN

Traveling on a budget? We've got you covered. Find a great deal on a vacation rental in Winchester starting at $37. Use the price filter at the top of the page to search for more specific prices.
809 S High St

No rating

·
Winchester
·
1 br
·
From
$37/night
Min stay: 30 nights
Property
Apartment · 1 Bed · 1 bath
Beautifully Renovated Studio 2 miles from the Marina
10

Excellent

·
Winchester
·
Studio
·
Sleeps 2
·
Lake · In Unit Laundry · Outdoor Space ·
From
$56/night
Check availability
Property
Apartment · Studio · 1 bath
Amenities
Lake
In Unit Laundry
Business Center
Wifi
Air Conditioning
Garage Parking
Furnished
Waterfront
Other spaces
Kitchen
Best Western Inn Winchester
8.3

Very good

·
Winchester
·
1 br
·
Sleeps 10
·
Fitness Center · Hot Tub · Free Parking ·
From
$87/night
Check availability
Property
Hotel · 1 Bed
Amenities
Fitness Center
Hot Tub
Free Parking
Wifi
Assigned Parking
Wheelchair Accessible
Furnished
Business Center
Other spaces
Workspace
"The Hawk Nest" cabin on Tims Ford Lake
10

Excellent

·
Winchester
·
2 br
·
Sleeps 4
·
Waterfront · Lake · Kitchen ·
From
$89/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Waterfront
Lake
Fitness Center
Furnished
Air Conditioning
Wifi
Oven
Other spaces
Kitchen
The Yellow Cottage by Tims Ford Lake
10

Excellent

·
Winchester
·
3 br
·
Sleeps 6
·
Lake · Wifi · Air Conditioning ·
From
$92/night
Check availability
Property
House · 3 Beds · 1 bath
Amenities
Lake
Wifi
Air Conditioning
Dishwasher
Business Center
Waterfront
Oven
Furnished
Other spaces
Kitchen
Beautiful 1920’s Home in Downtown Winchester

No rating

·
Winchester
·
4 br
·
Sleeps 10
·
Hardwood Floor · Oven · Air Conditioning ·
From
$94/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Hardwood Floor
Oven
Air Conditioning
Fireplace
Dishwasher
Wifi
In Unit Laundry
Furnished
Other spaces
Kitchen

Family-Friendly Vacation Rentals in Winchester, TN

Heading to Winchester for your next family vacation? Check out these family-friendly vacation rentals, which have more bedrooms and more space for you and your loved ones. Use the filters at the top of the page to narrow your search and find what you need.
Beautifully Renovated Studio 2 Miles From Marina!
8.8

Very good

·
Winchester
·
1 br
·
Sleeps 2
·
Furnished · In Unit Laundry · Free Parking ·
From
$109/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
In Unit Laundry
Free Parking
Smoking Allowed
Air Conditioning
Wifi
Assigned Parking
Other spaces
Kitchen
Newly Renovated Cozy Place Minutes From The Lake
8

Very good

·
Winchester
·
1 br
·
Sleeps 3
·
Furnished · Smoking Allowed · Free Parking ·
From
$108/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Furnished
Smoking Allowed
Free Parking
In Unit Laundry
Air Conditioning
Assigned Parking
Oven
Wifi
Other spaces
Kitchen
Cozy Tennessee Abode with Private Hot Tub and Fire Pit

No rating

·
Winchester
·
1 br
·
Sleeps 5
·
Free Parking · Furnished · Air Conditioning ·
From
$272/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Free Parking
Furnished
Air Conditioning
In Unit Laundry
Hot Tub
Wifi
Other spaces
Kitchen, Workspace
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Updated: November 30, 2023