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
Price filter
Type of place
Type of place filter
Show map
Search results; 234 homes in Winchester
234 homes in Winchester
Guest favourite
Guest favourite
Tiny home in Winchester
Highland Hideout
1 bedroom
,
·
1 bed
,
·
1 private bathroom
20–25 Sept
20–25 Sept
$941 SGD
Show price breakdown
for 5 nights
$941 SGD for 5 nights
,
·
4.91 out of 5 average rating, 46 reviews
4.91 (46)
Top guest favourite
Guest favourite
Rooms in Winchester
Shady Grace Equine B&B
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2.5 bathrooms
2.5 bathrooms
12–17 Sept
12–17 Sept
$740 SGD
Show price breakdown
for 5 nights
$740 SGD for 5 nights
4.98 out of 5 average rating, 54 reviews
4.98 (54)
Top guest favourite
Guest favourite
Home in Winchester
Welcome to Dancing Deer Acres!
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
20–25 Sept
20–25 Sept
$1,445 SGD
Show price breakdown
for 5 nights
$1,445 SGD for 5 nights
4.99 out of 5 average rating, 68 reviews
4.99 (68)
Guest favourite
Guest favourite
Home in Sardinia
Bradford Paradise
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
20–25 Oct
20–25 Oct
$1,546 SGD
$1,378 SGD
Show price breakdown
for 5 nights
Free cancellation
4.97 out of 5 average rating, 37 reviews
4.97 (37)
Home in Sardinia
Private 20 Acres|Pets| Hot Tub + Sauna Sleeps 11
4 bedrooms
4 bedrooms
,
·
8 beds
8 beds
,
·
3 bathrooms
3 bathrooms
27 Sept – 2 Oct
27 Sept – 2 Oct
$2,785 SGD
$2,462 SGD
Show price breakdown
for 5 nights
Free cancellation
4.85 out of 5 average rating, 244 reviews
4.85 (244)
Superhost
Superhost
Home in Winchester
Quiet Farm Escape | Fishing, Nature & Views
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
12–17 Sept
12–17 Sept
$1,950 SGD
Show price breakdown
for 5 nights
$1,950 SGD for 5 nights
New place to stay
New
Top guest favourite
Guest favourite
Cabin in Seaman
Amish-built cabin on pond/amazing view!
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
12–17 Sept
12–17 Sept
$1,503 SGD
Show price breakdown
for 5 nights
$1,503 SGD for 5 nights
4.98 out of 5 average rating, 103 reviews
4.98 (103)
Top guest favourite
Guest favourite
Cabin in West Union
"Clover" 1830s Cabin on Hills Fork Farm
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
14–19 Sept
14–19 Sept
$1,120 SGD
$981 SGD
Show price breakdown
for 5 nights
4.99 out of 5 average rating, 67 reviews
4.99 (67)
Guest favourite
Guest favourite
Cottage in West Union
Lucky Hooks
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
12–17 Sept
12–17 Sept
$1,145 SGD
$960 SGD
Show price breakdown
for 5 nights
4.93 out of 5 average rating, 87 reviews
4.93 (87)
Guest favourite
Guest favourite
Cabin in Peebles
Hunter Lodge (Pine Valley Cabins)
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
12–17 Sept
12–17 Sept
$1,075 SGD
Show price breakdown
for 5 nights
$1,075 SGD for 5 nights
4.94 out of 5 average rating, 35 reviews
4.94 (35)
Guest favourite
Guest favourite
Cabin in Peebles
Bunk House (Pine Valley Cabins)
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
12–17 Sept
12–17 Sept
$1,105 SGD
Show price breakdown
for 5 nights
$1,105 SGD for 5 nights
4.94 out of 5 average rating, 51 reviews
4.94 (51)
Superhost
Superhost
Cabin in West Union
Griffis Game Hunting and Getaway
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$1,321 SGD
$1,162 SGD
Show price breakdown
for 5 nights
4.87 out of 5 average rating, 52 reviews
4.87 (52)
Top guest favourite
Guest favourite
Farm stay in Hillsboro
A relaxing farmhouse getaway in the country.
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
26–31 Oct
26–31 Oct
$1,445 SGD
$1,261 SGD
Show price breakdown
for 5 nights
Free cancellation
4.97 out of 5 average rating, 92 reviews
4.97 (92)
Top guest favourite
Guest favourite
Home in Sardinia
30 Acre Retreat: Pond, Hot Tub, Disc Golf & More!
5 bedrooms
5 bedrooms
,
·
8 beds
8 beds
,
·
3 bathrooms
3 bathrooms
4–9 Nov
4–9 Nov
$2,674 SGD
Show price breakdown
for 5 nights
$2,674 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 36 reviews
5.0 (36)
Top guest favourite
Guest favourite
Cabin in Seaman
Cozy, Amish-built cabin/amazing sunset view!
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
12–17 Sept
12–17 Sept
$1,227 SGD
Show price breakdown
for 5 nights
$1,227 SGD for 5 nights
5.0 out of 5 average rating, 69 reviews
5.0 (69)
Guest favourite
Guest favourite
Home in Dover
Kenyatucky! For your stay or event!
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
19–24 Sept
19–24 Sept
$1,950 SGD
$1,703 SGD
Show price breakdown
for 5 nights
Free cancellation
4.88 out of 5 average rating, 26 reviews
4.88 (26)
Guest favourite
Guest favourite
Home in West Union
Finding Grace
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
17–22 Sept
17–22 Sept
$601 SGD
Show price breakdown
for 5 nights
$601 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Cabin in Peebles
Stream View Cabin near Serpents Mound
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
12–17 Sept
12–17 Sept
$829 SGD
Show price breakdown
for 5 nights
$829 SGD for 5 nights
4.52 out of 5 average rating, 82 reviews
4.52 (82)
Top guest favourite
Guest favourite
Cabin in Peebles
Meadow View Cabin
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
12–17 Sept
12–17 Sept
$3,818 SGD
$2,715 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 54 reviews
5.0 (54)
1
2
3
4
…
13