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

Search results; 132 homes in Winchester

Guest favourite

Loft in Winchester

The Bike Flat

2 bedrooms, 5 beds, 1 private bathroom

23–28 Aug

$765 SGD for 5 nights

,

4.92 out of 5 average rating, 182 reviews

Flat in Winchester

The Primrose inside historic commercial bldg

2 bedrooms, 3 beds, 1 bathroom

7–12 Aug

$869 SGD for 5 nights

4.93 out of 5 average rating, 74 reviews

Top guest favourite

Cabin in Winchester

Container Home GREAT Countryside Views COZY Stay

1 bedroom, 1 king bed, 1 bathroom

24–29 Aug

$718 SGD for 5 nights

4.96 out of 5 average rating, 196 reviews

Guest favourite

Flat in Winchester

Sugar Shack, a retro studio apartment

1 bedroom, 1 queen bed, 1 bathroom

2–7 Oct

$816 SGD for 5 nights

4.89 out of 5 average rating, 54 reviews

Home in Winchester

Charming Country Retreat

4 bedrooms, 5 beds, 1 bathroom

6–11 Aug

$1,851 SGD for 5 nights

New place to stay

Top guest favourite

Cabin in Jacksonville

Bunkhouse Seventy-Four

1 bedroom, 1 queen bed, 1 bathroom

7–12 Aug

$673 SGD for 5 nights

4.98 out of 5 average rating, 408 reviews

Guest favourite

Home in White Hall

The Humble Hideaway

3 bedrooms, 3 beds, 2 bathrooms

9–14 Aug

$846 SGD for 5 nights

4.92 out of 5 average rating, 106 reviews

Guest favourite

Home in Pittsfield

Florence Guest House

3 bedrooms, 5 beds, 2 bathrooms

17–22 Sept

$462 SGD for 5 nights

4.84 out of 5 average rating, 256 reviews

Guest favourite

Guest suite in Pittsfield

Florence Guest House--Loft Unit

1 bedroom, 3 beds, 1 bathroom

29 Aug – 3 Sept

$481 SGD for 5 nights

4.82 out of 5 average rating, 139 reviews

Hotel room in Jacksonville

King Bed | Super 8 Jacksonville | Free Breakfast

1 bedroom, 1 bathroom

3–8 Aug

$455 SGD for 5 nights

Top guest favourite

Cabin in Jacksonville

Audrey's Abode

2 bedrooms, 4 beds, 1 bathroom

18–23 Aug

$975 SGD for 5 nights

4.97 out of 5 average rating, 780 reviews

Top guest favourite

Flat in Murrayville

Peace on the Prairie - Studio Apartment

1 bedroom, 4 beds, 1 bathroom

1–6 Sept

$686 SGD for 5 nights

4.97 out of 5 average rating, 432 reviews

Superhost

Cabin in Hillview

Modern-Rustic Cabin, Nature Inspired

2 beds, 1 bathroom

5–10 Aug

Extended stay discount

4.86 out of 5 average rating, 49 reviews

Guest favourite

Home in White Hall

Cozy-Rose-Cottage

2 bedrooms, 3 beds, 1 bathroom

3–8 Aug

$819 SGD for 5 nights

4.92 out of 5 average rating, 88 reviews

Home in Alsey

Douglas Street Retreat

4 bedrooms, 5 beds, 2.5 bathrooms

13–18 Sept

$975 SGD for 5 nights

4.8 out of 5 average rating, 15 reviews

Top guest favourite

Home in Carrollton

Sunshine on Fifth

3 bedrooms, 4 beds, 2 bathrooms

4–9 Aug

$1,194 SGD for 5 nights

4.97 out of 5 average rating, 65 reviews

Flat in Jacksonville

Baker & Birch

2 bedrooms, 3 beds, 1 bathroom

9–14 Aug

$1,378 SGD for 5 nights

Room in Pittsfield

Quiet Queen Suite | Boutique Comfort, Private Bath

1 bed, 1.5 bathrooms

9–14 Aug

New place to stay

Guest favourite

Flat in Pittsfield

Pike County Haven: Retro Loft

1 bedroom, 2 beds, 1 bathroom

9–14 Aug

$865 SGD for 5 nights

5.0 out of 5 average rating, 21 reviews