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Search results; 141 homes in Winchester

Top guest favourite

Cabin in Winchester

Container Home GREAT Countryside Views COZY Stay

1 bedroom, 1 bed, 1 private bathroom

24–29 Aug

$717 SGD for 5 nights

,

4.96 out of 5 average rating, 196 reviews

Guest favourite

Loft in Winchester

The Bike Flat

2 bedrooms, 5 beds, 1 bathroom

23–28 Aug

$767 SGD for 5 nights

4.92 out of 5 average rating, 183 reviews

Flat in Winchester

The Primrose inside historic commercial bldg

2 bedrooms, 3 beds, 1 bathroom

12–17 Aug

$868 SGD for 5 nights

4.93 out of 5 average rating, 75 reviews

Home in Winchester

Charming Country Retreat

4 bedrooms, 5 beds, 1 bathroom

14–19 Aug

$1,849 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

2–7 Oct

$815 SGD for 5 nights

4.89 out of 5 average rating, 54 reviews

Top guest favourite

Cabin in Jacksonville

Bunkhouse Seventy-Four

1 bedroom, 1 queen bed, 1 bathroom

24–29 Aug

$672 SGD for 5 nights

4.98 out of 5 average rating, 411 reviews

Guest favourite

Home in White Hall

The Humble Hideaway

3 bedrooms, 3 beds, 2 bathrooms

16–21 Aug

$845 SGD for 5 nights

4.91 out of 5 average rating, 108 reviews

Top guest favourite

Cabin in Jacksonville

Audrey's Abode

2 bedrooms, 4 beds, 1 bathroom

19–24 Oct

$974 SGD for 5 nights

4.97 out of 5 average rating, 782 reviews

Cabin in Pittsfield

Spring Hill Lodge

2 bedrooms, 3 beds, 1 bathroom

12–17 Aug

$1,779 SGD for 5 nights

New place to stay

Guest favourite

Flat in Pittsfield

Pike County Haven: Retro Loft

1 bedroom, 2 beds, 1 bathroom

12–17 Aug

$871 SGD for 5 nights

5.0 out of 5 average rating, 22 reviews

Top guest favourite

Home in Meredosia

The Fricke Farm

2 bedrooms, 3 beds, 1.5 bathrooms

14–19 Oct

$1,097 SGD for 5 nights

4.98 out of 5 average rating, 61 reviews

Guest suite in Hamburg

3BR Hamburg Home, Sleeps 6, Wi-Fi, W/D, Kitchen.

3 bedrooms, 3 beds, 1 bathroom

12–17 Aug

$1,818 SGD for 5 nights

Guest favourite

Home in Roodhouse

Cozy Corner Bungalow

2 bedrooms, 4 beds, 1 bathroom

12–17 Aug

$818 SGD for 5 nights

4.93 out of 5 average rating, 40 reviews

Guest favourite

Home in Beardstown

Nostalgia on 5th St

4 bedrooms, 6 beds, 2 bathrooms

23–28 Aug

4.9 out of 5 average rating, 40 reviews

Guest favourite

Flat in Carrollton

Farmhouse Loft

2 bedrooms, 3 beds, 1 bathroom

6–11 Sept

$640 SGD for 5 nights

4.85 out of 5 average rating, 195 reviews

Guest favourite

Home in Jacksonville

Rees Residential

2 bedrooms, 3 beds, 1 bathroom

14–19 Aug

$1,479 SGD for 5 nights

4.86 out of 5 average rating, 49 reviews

Home in Alsey

Douglas Street Retreat

4 bedrooms, 5 beds, 2.5 bathrooms

13–18 Sept

$974 SGD for 5 nights

4.8 out of 5 average rating, 15 reviews

Top guest favourite

Home in White Hall

Cozy-Rose-Cottage

2 bedrooms, 3 beds, 1 bathroom

17–22 Aug

$818 SGD for 5 nights

4.92 out of 5 average rating, 89 reviews

Top guest favourite

Home in Beardstown

Country Star Retreat

3 bedrooms, 3 beds, 1 bathroom

12–17 Aug

$1,245 SGD for 5 nights

4.97 out of 5 average rating, 34 reviews