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Search results; 156 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, 197 reviews

Guest favourite

Loft in Winchester

The Bike Flat

2 bedrooms, 5 beds

23–28 Aug

$764 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

18–23 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

16–21 Aug

$1,774 SGD for 5 nights

New place to stay

Guest favourite

Flat in Winchester

Sugar Shack, a retro studio apartment

1 bedroom, 1 queen bed

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

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

16–21 Aug

4.91 out of 5 average rating, 108 reviews

Flat in Jacksonville

Baker & Birch

2 bedrooms, 3 beds

15–20 Sept

$1,441 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in White Hall

Cozy-Rose-Cottage

2 bedrooms, 3 beds

17–22 Aug

$819 SGD for 5 nights

4.92 out of 5 average rating, 89 reviews

Guest favourite

Home in Beardstown

Nostalgia on 5th St

4 bedrooms, 6 beds

14–19 Aug

4.9 out of 5 average rating, 40 reviews

Top guest favourite

Cabin in Jacksonville

Audrey's Abode

2 bedrooms, 4 beds

19–24 Oct

$974 SGD for 5 nights

4.97 out of 5 average rating, 783 reviews

Cabin in Pittsfield

Spring Hill Lodge

2 bedrooms, 3 beds

14–19 Aug

$1,780 SGD for 5 nights

New place to stay

Guest favourite

Home in Roodhouse

Cozy Corner Bungalow

2 bedrooms, 4 beds

23–28 Aug

$819 SGD for 5 nights

4.93 out of 5 average rating, 40 reviews

Guest favourite

Flat in Pittsfield

Pike County Haven: Retro Loft

1 bedroom, 2 beds

14–19 Aug

$865 SGD for 5 nights

5.0 out of 5 average rating, 22 reviews

Home in Carrollton

Cozy home in picturesque small town

3 bedrooms, 3 beds

30 Sept – 5 Oct

$733 SGD for 5 nights

4.82 out of 5 average rating, 185 reviews

Home in Alsey

Douglas Street Retreat

4 bedrooms, 5 beds

13–18 Sept

$975 SGD for 5 nights

4.8 out of 5 average rating, 15 reviews

Guest favourite

Cottage in Pearl

Beautiful Secluded Home With a breathtaking view

3 bedrooms, 5 beds

16–21 Aug

$1,329 SGD for 5 nights

4.96 out of 5 average rating, 97 reviews

Room in Pittsfield

Boutique Queen Suite I Private Bath + Fast WiFi

1 bed

16–21 Aug

New place to stay

Guest favourite

Guest suite in Pittsfield

Florence Guest House--Loft Unit

1 bedroom, 3 beds

29 Aug – 3 Sept

4.82 out of 5 average rating, 139 reviews