Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
Experiences
Experiences
Services
Services
Start your search
Location
Homes in Winchester
Check in / Check out
Any week
Guests
Add guests
Become a host
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Filters
Price
Type of place
Show map
Search results; 853 homes in Winchester
853 homes in Winchester
Top guest favourite
Guest favourite
Home in Winchester
Extend your Summer in TN~Golf~Fish~Hike Great deal
3 bedrooms
,
·
6 beds
,
·
3 private bathrooms
25–30 Aug
25–30 Aug
$1,456 SGD
$1,172 SGD
Show price breakdown
for 5 nights
,
·
4.95 out of 5 average rating, 77 reviews
4.95 (77)
Top guest favourite
Guest favourite
Home in Winchester
The Hangout on Heath Lane
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
6–11 Sept
6–11 Sept
$1,027 SGD
Show price breakdown
for 5 nights
$1,027 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 68 reviews
5.0 (68)
Guest favourite
Guest favourite
Home in Winchester
The Bourbon Embassy at Twin Creeks
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
30 Aug – 4 Sept
30 Aug – 4 Sept
$1,549 SGD
Show price breakdown
for 5 nights
$1,549 SGD for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Top guest favourite
Guest favourite
Home in Winchester
Lakeside Retreat Marina/Pool, Golf Cart, Game Room
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
7–12 Sept
7–12 Sept
$1,702 SGD
$1,407 SGD
Show price breakdown
for 5 nights
4.97 out of 5 average rating, 66 reviews
4.97 (66)
Guest favourite
Guest favourite
Flat in Winchester
Winchester's Premier Downtown Loft! Near The Lake!
2 bedrooms
2 bedrooms
,
·
2 king beds
2 king beds
23–28 Aug
23–28 Aug
$667 SGD
Show price breakdown
for 5 nights
$667 SGD for 5 nights
4.89 out of 5 average rating, 90 reviews
4.89 (90)
Flat in Winchester
Beautifully Renovated Studio 2 miles from Marina!
1 queen bed
1 queen bed
23–28 Aug
23–28 Aug
$655 SGD
$585 SGD
Show price breakdown
for 5 nights
4.86 out of 5 average rating, 63 reviews
4.86 (63)
Guest favourite
Guest favourite
Tiny home in Winchester
Tiny House
1 bedroom
1 bedroom
,
·
1 bed
1 bed
31 Aug – 5 Sept
31 Aug – 5 Sept
$832 SGD
Show price breakdown
for 5 nights
$832 SGD for 5 nights
4.95 out of 5 average rating, 86 reviews
4.95 (86)
Home in Winchester
Cozy Tims Ford lakehouse with private dock
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
20–25 Aug
20–25 Aug
$1,761 SGD
$1,453 SGD
Show price breakdown
for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Cabin in Tullahoma
Cozy Cabin close to Tims Ford Lake & Jack Daniels
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
22–27 Aug
22–27 Aug
$997 SGD
$803 SGD
Show price breakdown
for 5 nights
4.95 out of 5 average rating, 219 reviews
4.95 (219)
Guest favourite
Guest favourite
Home in Winchester
Dry Jack Tim-Hot Tub, Water Views, Marina
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
23–28 Aug
23–28 Aug
$1,587 SGD
$1,379 SGD
Show price breakdown
for 5 nights
4.84 out of 5 average rating, 31 reviews
4.84 (31)
Top guest favourite
Guest favourite
Townhouse in Winchester
Lovin Lake Life
5 bedrooms
5 bedrooms
,
·
7 beds
7 beds
23–28 Aug
23–28 Aug
$1,697 SGD
$1,329 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 48 reviews
5.0 (48)
Guest favourite
Guest favourite
Flat in Winchester
Unbeatable Charm & Convenience On The Square!
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
7–12 Sept
7–12 Sept
$798 SGD
Show price breakdown
for 5 nights
$798 SGD for 5 nights
4.89 out of 5 average rating, 72 reviews
4.89 (72)
Home in Winchester
The Yellow Cottage by Tims Ford Lake
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
20–25 Aug
20–25 Aug
$1,098 SGD
$822 SGD
Show price breakdown
for 5 nights
4.68 out of 5 average rating, 111 reviews
4.68 (111)
Guest favourite
Guest favourite
Home in Winchester
LakeLane Landing Privatedock Summer fun!
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
7–12 Sept
7–12 Sept
$1,886 SGD
$1,581 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Top guest favourite
Guest favourite
Home in Winchester
Meadow View Retreat
2 bedrooms
2 bedrooms
,
·
2 queen beds
2 queen beds
24–29 Aug
24–29 Aug
$1,113 SGD
Show price breakdown
for 5 nights
$1,113 SGD for 5 nights
4.98 out of 5 average rating, 85 reviews
4.98 (85)
Guest favourite
Guest favourite
Home in Tullahoma
Whiskey Trails Cottage
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
5–10 Sept
5–10 Sept
$1,046 SGD
$918 SGD
Show price breakdown
for 5 nights
4.96 out of 5 average rating, 82 reviews
4.96 (82)
Top guest favourite
Guest favourite
Cottage in Pelham
The Milk Barn Cottage
2 beds
2 beds
23–28 Aug
23–28 Aug
$828 SGD
Show price breakdown
for 5 nights
$828 SGD for 5 nights
5.0 out of 5 average rating, 568 reviews
5.0 (568)
Guest favourite
Guest favourite
Home in Winchester
Shady Cove Retreat With Peaceful Views & Firepit
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
20–25 Aug
20–25 Aug
$1,289 SGD
Show price breakdown
for 5 nights
$1,289 SGD for 5 nights
4.97 out of 5 average rating, 32 reviews
4.97 (32)
Top guest favourite
Guest favourite
Home in Winchester
Lakin It Easy at Twin Creeks
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
24–29 Aug
24–29 Aug
$1,679 SGD
$1,342 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 31 reviews
5.0 (31)
1
2
3
4
…
15