We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Search results; 152 homes in Winchester

Top guest favourite

Cabin in Winchester

Container Home GREAT Countryside Views COZY Stay

1 bedroom, 1 bed, 1 private bathroom

19–24 Jul

$722 SGD for 5 nights

,

4.96 out of 5 average rating, 191 reviews

Guest favourite

Loft in Winchester

The Bike Flat

2 bedrooms, 5 beds, 1 bathroom

22–27 Jul

$769 SGD for 5 nights

4.92 out of 5 average rating, 177 reviews

Home in Winchester

Charming Country Retreat

4 bedrooms, 5 beds, 1 bathroom

18–23 Jul

$1,823 SGD for 5 nights

New place to stay

Guest favourite

Flat in Winchester

Sugar Shack, a retro studio apartment

1 bedroom, 1 queen bed, 1 bathroom

20–25 Jul

$821 SGD for 5 nights

4.89 out of 5 average rating, 54 reviews

Flat in Winchester

The Primrose inside historic commercial bldg

2 bedrooms, 3 beds, 1 bathroom

3–8 Aug

$874 SGD for 5 nights

4.96 out of 5 average rating, 73 reviews

Top guest favourite

Cabin in Jacksonville

Bunkhouse Seventy-Four

1 bedroom, 1 queen bed, 1 bathroom

7–12 Aug

$676 SGD for 5 nights

4.98 out of 5 average rating, 404 reviews

Top guest favourite

Cabin in Jacksonville

Audrey's Abode

2 bedrooms, 4 beds, 1 bathroom

4–9 Oct

$980 SGD for 5 nights

4.97 out of 5 average rating, 777 reviews

Home in Alsey

Douglas Street Retreat

4 bedrooms, 5 beds, 2.5 bathrooms

21–26 Jul

$1,025 SGD for 5 nights

4.79 out of 5 average rating, 14 reviews

Guest favourite

Home in White Hall

Cozy-Rose-Cottage

2 bedrooms, 3 beds, 1 bathroom

16–21 Jul

$843 SGD for 5 nights

4.92 out of 5 average rating, 87 reviews

Guest favourite

Home in Pittsfield

Florence Guest House

3 bedrooms, 5 beds, 2 bathrooms

18–23 Aug

$464 SGD for 5 nights

4.84 out of 5 average rating, 256 reviews

Hotel in Pittsfield

Boutique Queen Suite I Private Bath + Fast WiFi

1 bedroom, 1 bed, 1.5 bathrooms

17–22 Jul

New home discount

New place to stay

Top guest favourite

Home in Beardstown

My Little Bungalow on Monroe Street.

2 bedrooms, 5 beds, 1.5 bathrooms

2–7 Aug

$718 SGD for 5 nights

4.98 out of 5 average rating, 319 reviews

Guest favourite

Home in White Hall

The Humble Hideaway

3 bedrooms, 3 beds, 2 bathrooms

9–14 Aug

$851 SGD for 5 nights

4.91 out of 5 average rating, 104 reviews

Guest favourite

Loft in Pittsfield

Historic Loft on Adams

1 bedroom, 1 bed, 1 bathroom

19–24 Jul

$584 SGD for 5 nights

4.9 out of 5 average rating, 94 reviews

Guest favourite

Hotel in Jacksonville

Charming downtown hotel above wine bar - Room 3

1 bedroom, 1 bed, 1 bathroom

18–23 Jul

$1,032 SGD for 5 nights

4.94 out of 5 average rating, 106 reviews

Top guest favourite

Flat in Murrayville

Peace on the Prairie - Studio Apartment

1 bedroom, 4 beds, 1 bathroom

19–24 Jul

$692 SGD for 5 nights

4.97 out of 5 average rating, 429 reviews

Guest favourite

Cottage in Pearl

Beautiful Secluded Home With a breathtaking view

3 bedrooms, 5 beds, 2 bathrooms

16–21 Jul

$1,398 SGD for 5 nights

4.96 out of 5 average rating, 96 reviews

Guest favourite

Home in Roodhouse

Cozy Corner Bungalow

2 bedrooms, 4 beds, 1 bathroom

20–25 Jul

$843 SGD for 5 nights

4.92 out of 5 average rating, 39 reviews

Guest favourite

Home in Jacksonville

Rees Residential

2 bedrooms, 3 beds, 1 bathroom

18–23 Jul

$1,428 SGD for 5 nights

4.85 out of 5 average rating, 46 reviews