Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Start your search
Location
Winchester
Check in / Check out
Any week
Guests
Add guests
Stays
Experiences
Online Experiences
Where
Navigate forward to access suggested results
Search by region
I’m flexible
I’m flexible
Europe
Europe
Italy
Italy
Caribbean
Caribbean
France
France
South America
South America
Check in
Add dates
Check out
Add dates
Who
Add guests
Search
Become a host
Sign up
Log in
Host your home
Host an experience
Help
Show map
392 stays
Filters
0
1 of 6 %{item_type}s showing
Superhost
Flat in Winchester
Downtown Renovated 1920's Gas Station
1 queen bed
22–29 Nov
$213 SGD
night
$213 SGD per night
4.93 (150)
1 of 6 %{item_type}s showing
Private room in Winchester
Lovely 1 bedroom casa, 1 living room with office.
1 bed
23 Feb – 2 Mar
$97 SGD
night
$97 SGD per night
New
1 of 6 %{item_type}s showing
Superhost
Flat in Winchester
Dreamweaver Bright 1BR 2 blocks to Walking Mall
1 bed
19–26 Sep
$164 SGD
night
$164 SGD per night
4.86 (7)
1 of 6 %{item_type}s showing
Flat in Winchester
Historic Wisteria House on Old Town Walking Mall
1 queen bed
8–15 Sep
$186 SGD
night
$186 SGD per night
5.0 (14)
1 of 6 %{item_type}s showing
Superhost
Flat in Winchester
Downtowner
3 beds
6–13 Dec
$176 SGD
night
$176 SGD per night
4.99 (154)
1 of 6 %{item_type}s showing
Loft in Winchester
Immerse yourself in Old Town Winchester
1 bed
8–15 Jun
$119 SGD
night
$119 SGD per night
4.71 (424)
1 of 6 %{item_type}s showing
Flat in Winchester
Private flat in historic Winchester property
1 queen bed
2–9 Jan
$126 SGD
night
$126 SGD per night
4.29 (14)
1 of 6 %{item_type}s showing
Guest suite in Winchester
Luxury CLEAN MODERN w/HBOMAX, 1mi to walking mall!
1 bed
4–11 Dec
$156 SGD
night
$156 SGD per night
5.0 (11)
1 of 5 %{item_type}s showing
Private room in Winchester
1 bedroom with private bathroom
2 beds
30 Aug – 6 Sep
$85 SGD
night
$85 SGD per night
New
1 of 6 %{item_type}s showing
Superhost
Home in Winchester
Cameron Charmer
2 queen beds
15–22 Nov
$224 SGD
night
$224 SGD per night
4.96 (108)
1 of 6 %{item_type}s showing
Superhost
Home in Winchester
Newly Renovated Cozy Cottage
1 queen bed
3–10 Jan
$121 SGD
night
$121 SGD per night
4.91 (46)
1 of 6 %{item_type}s showing
Superhost
Flat in Winchester
Nostalgia Lane in the heart of the city
3 beds
29 Oct – 5 Nov
$209 SGD
night
$209 SGD per night
4.9 (124)
1 of 6 %{item_type}s showing
Superhost
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
2 beds
8–15 May
$154 SGD
night
$154 SGD per night
4.97 (59)
1 of 6 %{item_type}s showing
Superhost
Home in Winchester
THE FARMHOUSE-ISH PLACE
2 beds
18–25 Nov
$217 SGD
night
$217 SGD per night
4.89 (38)
1 of 6 %{item_type}s showing
Home in Winchester
Classic Updated 3 BR brick home w/ bright sunroom
3 queen beds
13–20 Jan
$335 SGD
night
$335 SGD per night
5.0 (7)
1 of 6 %{item_type}s showing
Superhost
Flat in Winchester
Morocco Loft overlooking the city
3 beds
4–11 Sep
$190 SGD
night
$190 SGD per night
4.67 (36)
1 of 6 %{item_type}s showing
Superhost
Cottage in Winchester
Escape to Foxy, Your Private Cottage at Fox Meadow
1 queen bed
19–26 Apr
$324 SGD
night
$324 SGD per night
4.98 (130)
1 of 6 %{item_type}s showing
Superhost
Cottage in Winchester
Lockley Cottage at Historic Perry Farm
2 beds
2–9 Jan
$102 SGD
night
$102 SGD per night
4.95 (19)
1 of 6 %{item_type}s showing
Superhost
Flat in Winchester
The Loudoun Luxe
2 beds
1–8 Dec
$220 SGD
night
$220 SGD per night
4.94 (17)
1 of 6 %{item_type}s showing
Flat in Winchester
Old Town Loft In Highly Desirable Area Downtown
1 queen bed
2–9 Dec
$224 SGD
night
$224 SGD per night
5.0 (36)
1
2
3
4
…
15
