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Search results; 154 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

$762 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 182 reviews

Flat in Winchester

The Primrose inside historic commercial bldg

2 bedrooms, 3 beds, 1 bathroom

11–16 Aug

$867 SGD for 5 nights

Free cancellation

4.93 out of 5 average rating, 75 reviews

Home in Winchester

Charming Country Retreat

4 bedrooms, 5 beds, 1 bathroom

10–15 Aug

$1,810 SGD for 5 nights

Free cancellation

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

Free cancellation

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

9–14 Aug

$671 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 410 reviews

Top guest favourite

Cabin in Jacksonville

Audrey's Abode

2 bedrooms, 4 beds, 1 bathroom

4–9 Oct

$973 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 781 reviews

Guest favourite

Home in White Hall

The Humble Hideaway

3 bedrooms, 3 beds, 2 bathrooms

9–14 Aug

$845 SGD for 5 nights

Free cancellation

4.91 out of 5 average rating, 107 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

Free cancellation

4.92 out of 5 average rating, 89 reviews

Guest favourite

Hotel in Jacksonville

Charming downtown hotel above wine bar - Room 3

1 bedroom, 1 bed, 1 bathroom

9–14 Aug

$988 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 109 reviews

Guest favourite

Cottage in Pearl

Beautiful Secluded Home With a breathtaking view

3 bedrooms, 5 beds, 2 bathrooms

16–21 Aug

$1,327 SGD for 5 nights

4.96 out of 5 average rating, 97 reviews

Guest favourite

Home in Beardstown

Nostalgia on 5th St

4 bedrooms, 6 beds, 2 bathrooms

23–28 Aug

$1,286 SGD for 5 nights

Free cancellation

4.9 out of 5 average rating, 40 reviews

Top guest favourite

Holiday home in Meredosia

Scenic 3 bedroom Wildlife Retreat

3 bedrooms, 5 beds, 1 bathroom

12–17 Aug

$865 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 97 reviews

Guest suite in Hamburg

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

3 bedrooms, 3 beds, 1 bathroom

8–13 Aug

$1,757 SGD for 5 nights

Free cancellation

Guest favourite

Cabin in Kampsville

Farm Stay in Illinois with Private Fishing Pond

1 bedroom, 3 queen beds, 1 bathroom

16–21 Aug

$1,311 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 19 reviews

Top guest favourite

Flat in Beardstown

The VanderWaal

2 bedrooms, 2 beds, 1 bathroom

17–22 Aug

$1,320 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 27 reviews

Top guest favourite

Home in Pleasant Plains

Hay Rake Country Acres-Peaceful Getaway-Sleeps 8

4 bedrooms, 5 beds, 2 bathrooms

9–14 Aug

$1,417 SGD for 5 nights

5.0 out of 5 average rating, 13 reviews

Guest favourite

Flat in Pittsfield

Pike County Haven: Retro Loft

1 bedroom, 2 beds, 1 bathroom

9–14 Aug

$864 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 22 reviews

Top guest favourite

Home in Carrollton

Sunshine on Fifth

3 bedrooms, 4 beds, 2 bathrooms

20–25 Aug

$1,108 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 65 reviews