Vacation Rentals in Winchester, TN

PRICE PER NIGHT

ACCOMMODATION TYPES

Downtown Winchester (Walk to Tim’s Ford Lake!)
10

Excellent

·
Winchester
·
2 br
·
Sleeps 4
·
Hot Tub · Outdoor Space · Waterfront ·
From
$229/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Hot Tub
Waterfront
Lake
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Other spaces
Kitchen
On the water with Dock & Great Location
9.5

Excellent

·
Winchester
·
2 br
·
Sleeps 6
·
Ski In Ski Out · Fitness Center · Balcony ·
From
$267/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Ski In Ski Out
Fitness Center
Fireplace
Waterfront
Lake
Air Conditioning
In Unit Laundry
Dishwasher
Other spaces
Balcony, Workspace, Kitchen
NEW! Spacious Lakefront Retreat w/ Hot Tub + Dock!
10

Excellent

·
Winchester
·
3 br
·
Sleeps 14
·
Cable · Microwave · Central Heat ·
From
$175/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Cable
Microwave
Central Heat
Tv
Walk In Closets
Ceiling Fan
Free Parking
Fireplace
Other spaces
Kitchen
Modern Luxury Retreat: Walk to Tims Ford Lake!
10

Excellent

·
Winchester
·
4 br
·
Sleeps 10
·
Garden · Cable · Toiletries ·
From
$234/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Cable
Toiletries
Microwave
Central Heat
Tv
Walk In Closets
Ceiling Fan
Pool
Other spaces
Garden, Kitchen
Vibrant Family House: Steps to Tims Ford Lake
10

Excellent

·
Winchester
·
4 br
·
Sleeps 11
·
Toiletries · Microwave · Central Heat ·
From
$220/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Toiletries
Microwave
Central Heat
Tv
Walk In Closets
Ceiling Fan
Free Parking
Fireplace
Other spaces
Kitchen
Vibrant Family House Steps to Tims Ford Lake
10

Excellent

·
Winchester
·
4 br
·
Sleeps 11
·
Free Parking · Fireplace · In Unit Laundry ·
From
$301/night
Check availability
Property
Apartment · 4 Beds · 3 baths
Amenities
Free Parking
Fireplace
In Unit Laundry
Dishwasher
Oven
Furnished
Wifi
Other spaces
Kitchen
Luxe Home with Boat Dock, Tims Ford Lake Views!

No reviews

·
Winchester
·
3 br
·
Sleeps 12
·
Free Parking · In Unit Laundry · Dishwasher ·
From
$495/night
Check availability
Property
Apartment · 3 Beds · 4 baths
Amenities
Free Parking
In Unit Laundry
Dishwasher
Oven
Furnished
Wifi
Other spaces
Kitchen
The Yellow Cottage By Tims Ford Lake
9.3

Excellent

·
Winchester
·
3 br
·
Sleeps 6
·
Smoking Allowed · Assigned Parking · Workspace ·
From
$151/night
Check availability
Property
Apartment · 3 Beds · 1 bath
Amenities
Smoking Allowed
Assigned Parking
Free Parking
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Other spaces
Workspace, Kitchen

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Newly Renovated Cozy Place Minutes From The Lake
8

Very good

·
Winchester
·
1 br
·
Sleeps 3
·
Smoking Allowed · Assigned Parking · Free Parking ·
From
$89/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Smoking Allowed
Assigned Parking
Free Parking
Air Conditioning
In Unit Laundry
Oven
Furnished
Wifi
Other spaces
Kitchen
3 Bedroom Cozy Home Minutes From Tims Ford Lake
9.7

Excellent

·
Winchester
·
3 br
·
Sleeps 6
·
Smoking Allowed · Assigned Parking · Free Parking ·
From
$97/night
Check availability
Property
Apartment · 3 Beds · 1 bath
Amenities
Smoking Allowed
Assigned Parking
Free Parking
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Other spaces
Kitchen
Gorgeous Renovated Home With Open Floor Plan And Large Lot
10

Excellent

·
Winchester
·
3 br
·
Sleeps 6
·
Smoking Allowed · Assigned Parking · Free Parking ·
From
$144/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Smoking Allowed
Assigned Parking
Free Parking
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Other spaces
Kitchen
Beautiful And Spacious Fully Renovated Farmhouse
10

Excellent

·
Winchester
·
4 br
·
Sleeps 8
·
Smoking Allowed · Assigned Parking · Workspace ·
From
$188/night
Check availability
Property
Apartment · 4 Beds · 3 baths
Amenities
Smoking Allowed
Assigned Parking
Free Parking
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Other spaces
Workspace, Kitchen
Beautifully Renovated Studio 2 Miles From The Marina
7.8

Very good

·
Winchester
·
1 br
·
Sleeps 2
·
Smoking Allowed · Assigned Parking · Free Parking ·
From
$99/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Smoking Allowed
Assigned Parking
Free Parking
Air Conditioning
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
Cozy Cottage with Private Yard Pet Friendly!

No reviews

·
Winchester
·
2 br
·
Sleeps 7
·
Free Parking · Outdoor Space · Fireplace ·
From
$171/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Free Parking
Fireplace
Dishwasher
Oven
Furnished
Wifi
Other spaces
Kitchen
Luxurious Waterfront Oasis on Tims Ford Lake!
9.7

Excellent

·
Winchester
·
3 br
·
Sleeps 8
·
Fireplace · Waterfront · Lake ·
From
$385/night
Check availability
Property
Apartment · 3 Beds · 3 baths
Amenities
Fireplace
Waterfront
Lake
Furnished
Wifi
Other spaces
Kitchen
Spacious Lakefront Retreat with Hot Tub and Dock!

No reviews

·
Winchester
·
3 br
·
Sleeps 14
·
Hot Tub · Free Parking · Fireplace ·
From
$440/night
Check availability
Property
Apartment · 3 Beds · 3 baths
Amenities
Hot Tub
Free Parking
Fireplace
Waterfront
Lake
In Unit Laundry
Dishwasher
Oven
Other spaces
Kitchen
Lakefront: Dock, Hot Tub, Fire Pit & Home Theater

No reviews

·
Winchester
·
2 br
·
Sleeps 4
·
Assigned Parking · Workspace · Free Parking ·
From
$194/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Assigned Parking
Free Parking
Fireplace
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Other spaces
Workspace, Kitchen
*NEW* Twin Creeks Modern Farmhouse with Golf Cart!
9.8

Excellent

·
Winchester
·
5 br
·
Sleeps 14
·
Pool · Workspace · Outdoor Space ·
From
$375/night
Check availability
Property
House · 5 Beds · 4 baths
Amenities
Pool
Fireplace
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Wifi
Other spaces
Workspace, Kitchen
NEW! Luxe Home w/ Boat Dock, Tims Ford Lake Views!
10

Excellent

·
Winchester
·
3 br
·
Sleeps 12
·
Toiletries · Microwave · Central Heat ·
From
$400/night
Check availability
Property
House · 3 Beds · 4 baths
Amenities
Toiletries
Microwave
Central Heat
Tv
Walk In Closets
Ceiling Fan
Free Parking
Lake
Other spaces
Kitchen
Luxurious Waterfront Oasis on Tims Ford Lake!
10

Excellent

·
Winchester
·
3 br
·
Sleeps 8
·
Garden · Toiletries · Tv ·
From
$250/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Toiletries
Tv
Walk In Closets
Ceiling Fan
Pool
Fireplace
Lake
Wifi
Other spaces
Garden, Kitchen
NEW! Spacious Lakefront Retreat w/ Hot Tub + Dock!
10

Excellent

·
Winchester
·
3 br
·
Sleeps 14
·
On Site Laundry · Hot Tub · Ceiling Fan ·
From
$411/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
On Site Laundry
Hot Tub
Ceiling Fan
Fireplace
Waterfront
Lake
Air Conditioning
In Unit Laundry
Other spaces
Kitchen
Lakefront Luxury on Tims Ford Lake
10

Excellent

·
Winchester
·
4 br
·
Sleeps 10
·
Hot Tub · Waterfront · Lake ·
From
$893/night
Check availability
Property
House · 4 Beds · 4 baths
Amenities
Hot Tub
Waterfront
Lake
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Other spaces
Kitchen
NEW! Tim's Ford Lakefront Home
10

Excellent

·
Winchester
·
4 br
·
Sleeps 8
·
Pool · Balcony · Outdoor Space ·
From
$542/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Pool
Fireplace
Waterfront
Lake
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Other spaces
Balcony, Kitchen
Vibrant Family House: Steps to Tims Ford Lake
10

Excellent

·
Winchester
·
4 br
·
Sleeps 11
·
Central Heat · Ceiling Fan · Workspace ·
From
$248/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Central Heat
Ceiling Fan
Fireplace
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Other spaces
Workspace, Kitchen
NEW-Lakefront Luxury-2 King Suites-Boat Dock+Slip
10

Excellent

·
Winchester
·
3 br
·
Sleeps 10
·
Hardwood Floor · Walk In Closets · Balcony ·
From
$150/night
Check availability
Property
House · 3 Beds · 5 baths
Amenities
Hardwood Floor
Walk In Closets
Waterfront
Lake
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Other spaces
Balcony, Workspace, Kitchen
SERENITY NOW LAKEVIEW
9.3

Excellent

·
Winchester
·
4 br
·
Sleeps 10
·
Pool · Balcony · Outdoor Space ·
From
$340/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Pool
Fireplace
Waterfront
Lake
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Other spaces
Balcony, Kitchen
Awesome Home close to the Lake.
8.4

Very good

·
Winchester
·
3 br
·
Sleeps 6
·
Workspace · Outdoor Space · Waterfront ·
From
$66/night
Check availability
Property
House · 3 Beds · 1 bath
Amenities
Waterfront
Lake
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Wifi
Other spaces
Workspace, Kitchen
Lakeside Retreat w/ Private Dock and lake access

No reviews

·
Winchester
·
3 br
·
Sleeps 12
·
Ev Charging · Fitness Center · Workspace ·
From
$629/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Ev Charging
Fitness Center
Waterfront
Lake
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Other spaces
Workspace, Kitchen
NEW 2021 Tims Ford Lake Home - Private covered dock - Hot Tub
9.9

Excellent

·
Winchester
·
4 br
·
Sleeps 12
·
High Ceilings · Fitness Center · Hot Tub ·
From
$400/night
Check availability
Property
House · 4 Beds · 6 baths
Amenities
High Ceilings
Fitness Center
Hot Tub
Fireplace
Waterfront
Lake
Air Conditioning
In Unit Laundry
Other spaces
Balcony, Kitchen
Beautiful And Spacious Fully Renovated Farmhouse
8.6

Very good

·
Winchester
·
4 br
·
Sleeps 8
·
Air Conditioning · In Unit Laundry · Dishwasher ·
From
$107/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Wifi
Garage Parking
Business Center
Other spaces
Kitchen
The Yellow Cottage by Tims Ford Lake
9.5

Excellent

·
Winchester
·
3 br
·
Sleeps 6
·
Waterfront · Lake · Air Conditioning ·
From
$87/night
Check availability
Property
House · 3 Beds · 1 bath
Amenities
Waterfront
Lake
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Wifi
Other spaces
Kitchen
New! close to town lake view home! Gorgeous water views w/ dock/boat slip.
10

Excellent

·
Winchester
·
3 br
·
Sleeps 12
·
Ski In Ski Out · Mountains · Ceiling Fan ·
From
$129/night
Check availability
Property
House · 3 Beds · 4 baths
Amenities
Ski In Ski Out
Mountains
Ceiling Fan
Waterfront
Lake
Air Conditioning
In Unit Laundry
Dishwasher
Other spaces
Balcony, Workspace, Kitchen
New! Tranquil lake view home close to town
10

Excellent

·
Winchester
·
3 br
·
Sleeps 13
·
High Ceilings · Ski In Ski Out · On Site Laundry ·
From
$99/night
Check availability
Property
House · 3 Beds · 4 baths
Amenities
High Ceilings
Ski In Ski Out
On Site Laundry
Mountains
Fitness Center
Ceiling Fan
Waterfront
Lake
Other spaces
Balcony, Workspace, Kitchen
Million Dollar Views: Lakefront, Dock, Kayaks+More

No reviews

·
Winchester
·
5 br
·
Sleeps 14
·
Assigned Parking · Workspace · Free Parking ·
From
$494/night
Check availability
Property
Apartment · 5 Beds · 3 baths
Amenities
Assigned Parking
Free Parking
Fireplace
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Other spaces
Workspace, Kitchen
Unbeatable Luxury, Lake Views, Private Dock
10

Excellent

·
Winchester
·
7 br
·
Sleeps 14
·
Balcony · Fireplace · Waterfront ·
From
$970/night
Check availability
Property
House · 7 Beds · 7 baths
Amenities
Fireplace
Waterfront
Lake
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Other spaces
Balcony, Kitchen
Lakefront Home, With Hot Tub and Boat deck! Backyard is On the water!
9.9

Excellent

·
Winchester
·
3 br
·
Sleeps 8
·
Hot Tub · Outdoor Space · Waterfront ·
From
$311/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Hot Tub
Waterfront
Lake
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Other spaces
Kitchen
Cozy 3b/2b home in Winchester 1.4 miles from Twin Creeks marina!

No reviews

·
Winchester
·
3 br
·
Sleeps 8
·
Workspace · Waterfront · Lake ·
From
$111/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Waterfront
Lake
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Wifi
Other spaces
Workspace, Kitchen
Cozy new townhome--2 min drive to Tims Ford Lake and marina

No reviews

·
Winchester
·
2 br
·
Sleeps 4
·
Hardwood Floor · Walk In Closets · Outdoor Space ·
From
$225/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Hardwood Floor
Walk In Closets
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Wifi
Other spaces
Kitchen
NEW Lakehouse at Twin Creeks Marina with Lake View

No reviews

·
Winchester
·
4 br
·
Sleeps 12
·
Pool · Balcony · Outdoor Space ·
From
$320/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Pool
Fireplace
Waterfront
Lake
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Other spaces
Balcony, Kitchen
Tims Ford Lake, Sewanee, and Historic Downtown Winchester
10

Excellent

·
Winchester
·
3 br
·
Sleeps 8
·
Mountains · Air Conditioning · In Unit Laundry ·
From
$259/night
Check availability
Property
House · 3 Beds · 1 bath
Amenities
Mountains
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Wifi
Other spaces
Kitchen
Waterside Cottage on Tims Ford Lake at Twin Creeks Resort

No reviews

·
Winchester
·
4 br
·
Sleeps 12
·
Balcony · Waterfront · Lake ·
From
$352/night
Check availability
Property
House · 4 Beds · 3 baths
Amenities
Waterfront
Lake
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Wifi
Other spaces
Balcony, Kitchen
Best Western Inn Winchester
8.3

Very good

·
Winchester
·
1 br
·
Sleeps 10
·
Carpet · On Site Laundry · Smoking Allowed ·
From
$87/night
Check availability
Property
Hotel · 1 Bed
Amenities
Carpet
On Site Laundry
Smoking Allowed
Hot Tub
Assigned Parking
Free Parking
Air Conditioning
Furnished
Other spaces
Workspace
Easy Peasy -lakefront home Tim’s Ford Lake *golf cart seats 6, in Twin Creeks
9.9

Excellent

·
Winchester
·
4 br
·
Sleeps 12
·
Pool · Assigned Parking · Balcony ·
From
$500/night
Check availability
Property
House · 4 Beds · 5 baths
Amenities
Pool
Assigned Parking
Fireplace
Waterfront
Lake
Air Conditioning
In Unit Laundry
Dishwasher
Other spaces
Balcony, Kitchen
Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK
10

Excellent

·
Winchester
·
5 br
·
Sleeps 19
·
Walk In Closets · Outdoor Space · Waterfront ·
From
$485/night
Check availability
Property
House · 5 Beds · 4 baths
Amenities
Walk In Closets
Waterfront
Lake
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Other spaces
Kitchen
Sunny lake house in resort community.

No reviews

·
Winchester
·
3 br
·
Sleeps 8
·
Pool · Air Conditioning · In Unit Laundry ·
From
$119/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Pool
Air Conditioning
In Unit Laundry
Furnished
Wifi
Swimming Pool
Other spaces
Kitchen
"The Hawk Nest" cabin on Tims Ford Lake
10

Excellent

·
Winchester
·
2 br
·
Sleeps 4
·
Fitness Center · Outdoor Space · Waterfront ·
From
$99/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Fitness Center
Waterfront
Lake
Air Conditioning
Oven
Furnished
Wifi
Other spaces
Kitchen
LAKESIDE at Twin Creeks- 7 minute walk to marina!
9.9

Excellent

·
Winchester
·
4 br
·
Sleeps 14
·
Beach · On Site Laundry · Pool ·
From
$247/night
Check availability
Property
House · 4 Beds · 4 baths
Amenities
Beach
On Site Laundry
Pool
Waterfront
Lake
Air Conditioning
In Unit Laundry
Dishwasher
Other spaces
Kitchen
*NEW* Lake Life Living @Twin Creeks - Sleeps 13

No reviews

·
Winchester
·
5 br
·
Sleeps 13
·
Pool · Fireplace · Waterfront ·
From
$571/night
Check availability
Property
House · 5 Beds · 3 baths
Amenities
Pool
Fireplace
Waterfront
Lake
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Other spaces
Kitchen
FIREFLY FARMHOUSE IN NOSTALGIC PASTORAL SETTING
10

Excellent

·
Winchester
·
3 br
·
Sleeps 5
·
Mountains · Workspace · Fireplace ·
From
$169/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Mountains
Fireplace
Air Conditioning
In Unit Laundry
Dishwasher
Oven
Furnished
Wifi
Other spaces
Workspace
Lake View Cottage on Tims Ford Lake

No reviews

·
Winchester
·
3 br
·
Sleeps 8
·
Pool · Waterfront · Lake ·
From
$100/night
Check availability
Property
House · 3 Beds · 4 baths
Amenities
Pool
Waterfront
Lake
Air Conditioning
In Unit Laundry
Furnished
Wifi
Swimming Pool
Showing 1 - 50 of 89 results
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Home > Tennessee Vacation Rentals > Winchester Vacation Rentals
Updated: March 22, 2023

Learn about vacation rentals in

Winchester

Explore 90 vacation rentals near Winchester, Tennessee. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Winchester, you can see photos of Winchester vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Winchester vacation rentals in specific areas. Whether you’re looking for a Winchester staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Winchester is $66 per night and the highest price is $970 per night.
6 of the vacation rentals near Winchester are apartments or condos. The average bathroom count for this property type is 1. The median price for these vacation units is $97 per night. There are currently 3 vacation units under this price. 79 of the vacation rentals near Winchester are houses. The average bathroom count for a vacation house near Winchester is 3. The average price for vacation houses near Winchester is $310 per night. There are 45 vacation homes under this price. The most common amenities for vacation rentals near Winchester are: furnished, wifi, and kitchen. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.

1 bed rentals

5 available

2 bed rentals

8 available

3 bed rentals

41 available

4+ bed rentals

33 available

Vacation Rentals in Winchester, TN FAQ

How many vacation rentals in Winchester are available?

There are currently 90 vacation rentals in Winchester available. Our vacation rentals in Winchester include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.

Are there any pet friendly vacation rentals in Winchester?

Yes, right now there are 30 pet friendly vacation rentals in Winchester. A pet friendly vacation rental in Winchester means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.

Are there any vacation rentals in Winchester with a pool?

Yes there are vacation rentals with a pool available in Winchester, TN. View more detailed vacation spots on Vacations by Zumper.

Are there any vacation rentals in Winchester with internet access?

As of March 22, 2023, there are vacation rentals with internet access available in Winchester, Tennessee. Check out more enjoyable destinations on Vacations by Zumper.

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