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Search results; 152 homes in Winchester

Guest favourite

Flat in Winchester

Sugar Shack, a retro studio apartment

1 bedroom, 1 bed, 1 private bathroom

2–7 Oct

$817 SGD for 5 nights

,

4.89 out of 5 average rating, 54 reviews

Guest favourite

Loft in Winchester

The Bike Flat

2 bedrooms, 5 beds

23–28 Aug

$766 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

11–16 Aug

$870 SGD for 5 nights

4.93 out of 5 average rating, 74 reviews

Home in Winchester

Charming Country Retreat

4 bedrooms, 5 beds

6–11 Aug

$1,853 SGD for 5 nights

New place to stay

Top guest favourite

Cabin in Winchester

Container Home GREAT Countryside Views COZY Stay

1 bedroom, 1 king bed

24–29 Aug

$719 SGD for 5 nights

4.96 out of 5 average rating, 196 reviews

Top guest favourite

Cabin in Jacksonville

Bunkhouse Seventy-Four

1 bedroom, 1 queen bed

9–14 Aug

$673 SGD for 5 nights

4.98 out of 5 average rating, 408 reviews

Top guest favourite

Cabin in Jacksonville

Audrey's Abode

2 bedrooms, 4 beds

18–23 Aug

$976 SGD for 5 nights

4.97 out of 5 average rating, 780 reviews

Guest favourite

Home in White Hall

The Humble Hideaway

3 bedrooms, 3 beds

9–14 Aug

$847 SGD for 5 nights

4.92 out of 5 average rating, 106 reviews

Top guest favourite

Home in Mount Sterling

Cozy Cottage 405

2 bedrooms, 2 queen beds

12–17 Aug

$1,033 SGD for 5 nights

4.94 out of 5 average rating, 17 reviews

Guest favourite

Home in Beardstown

Nostalgia on 5th St

4 bedrooms, 6 beds

23–28 Aug

$1,295 SGD for 5 nights

4.9 out of 5 average rating, 39 reviews

Top guest favourite

Home in Meredosia

The Fricke Farm

2 bedrooms, 3 beds

14–19 Oct

$1,100 SGD for 5 nights

4.98 out of 5 average rating, 61 reviews

Home in Pittsfield

Newly remodeled home

2 bedrooms, 2 queen beds

9–14 Aug

4.87 out of 5 average rating, 55 reviews

Guest favourite

Farm stay in Carrollton

Peaceful Country Stay- The Carrollton Farmhouse

3 bedrooms, 5 beds

21–26 Aug

$1,324 SGD for 5 nights

5.0 out of 5 average rating, 51 reviews

Guest favourite

Home in White Hall

Cozy-Rose-Cottage

2 bedrooms, 3 beds

17–22 Aug

$820 SGD for 5 nights

4.92 out of 5 average rating, 88 reviews

Guest favourite

Loft in Pittsfield

Historic Loft on Adams

1 bedroom, 1 bed

9–14 Aug

$565 SGD for 5 nights

4.91 out of 5 average rating, 95 reviews

Top guest favourite

Loft in Virginia

Two Doors Down Loft, Virginia-Lincoln territory!

2 queen beds

1–6 Sept

$483 SGD for 5 nights

4.95 out of 5 average rating, 212 reviews

Home in Alsey

Douglas Street Retreat

4 bedrooms, 5 beds

13–18 Sept

$977 SGD for 5 nights

4.8 out of 5 average rating, 15 reviews

Guest suite in Hamburg

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

3 bedrooms, 3 beds

5–10 Aug

$1,823 SGD for 5 nights

Guest favourite

Cottage in Pearl

Beautiful Secluded Home With a breathtaking view

3 bedrooms, 5 beds

9–14 Aug

$1,331 SGD for 5 nights

4.96 out of 5 average rating, 97 reviews