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Search results; 147 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

$718 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

$765 SGD for 5 nights

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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

$869 SGD for 5 nights

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Free cancellation

4.93 out of 5 average rating, 74 reviews

Home in Winchester

Charming Country Retreat

4 bedrooms, 5 beds, 1 bathroom

6–11 Aug

$1,852 SGD for 5 nights

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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

$816 SGD for 5 nights

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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

$673 SGD for 5 nights

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4.98 out of 5 average rating, 408 reviews

Top guest favourite

Cabin in Jacksonville

Audrey's Abode

2 bedrooms, 4 beds, 1 bathroom

18–23 Aug

$975 SGD for 5 nights

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Free cancellation

4.97 out of 5 average rating, 780 reviews

Flat in Jacksonville

Baker & Birch

2 bedrooms, 3 beds, 1 bathroom

9–14 Aug

$1,379 SGD for 5 nights

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Free cancellation

Guest favourite

Home in White Hall

The Humble Hideaway

3 bedrooms, 3 beds, 2 bathrooms

9–14 Aug

$847 SGD for 5 nights

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Free cancellation

4.92 out of 5 average rating, 106 reviews

Home in Pittsfield

Newly remodeled home

2 bedrooms, 2 queen beds, 1 bathroom

9–14 Aug

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4.87 out of 5 average rating, 55 reviews

Guest favourite

Loft in Pittsfield

Historic Loft on Adams

1 bedroom, 1 bed, 1 bathroom

9–14 Aug

$565 SGD for 5 nights

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4.91 out of 5 average rating, 95 reviews

Guest favourite

Home in Beardstown

Nostalgia on 5th St

4 bedrooms, 6 beds, 2 bathrooms

23–28 Aug

$1,294 SGD for 5 nights

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4.9 out of 5 average rating, 39 reviews

Guest favourite

Home in White Hall

Cozy-Rose-Cottage

2 bedrooms, 3 beds, 1 bathroom

17–22 Aug

$820 SGD for 5 nights

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4.92 out of 5 average rating, 88 reviews

Top guest favourite

Home in Meredosia

The Fricke Farm

2 bedrooms, 3 beds, 1.5 bathrooms

14–19 Oct

$1,099 SGD for 5 nights

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4.98 out of 5 average rating, 61 reviews

Guest favourite

Rooms in Pittsfield

Sloth Lodging (Upper Level)

3 bedrooms, 3 beds, 1 bathroom

5–10 Aug

$605 SGD for 5 nights

4.89 out of 5 average rating, 55 reviews

Guest favourite

Farm stay in Carrollton

Peaceful Country Stay- The Carrollton Farmhouse

3 bedrooms, 5 beds, 1.5 bathrooms

21–26 Aug

$1,323 SGD for 5 nights

5.0 out of 5 average rating, 51 reviews

Top guest favourite

Loft in Virginia

Two Doors Down Loft, Virginia-Lincoln territory!

2 queen beds, 1.5 bathrooms

1–6 Sept

$482 SGD for 5 nights

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4.95 out of 5 average rating, 212 reviews

Guest suite in Hamburg

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

3 bedrooms, 3 beds, 1 bathroom

5–10 Aug

$1,821 SGD for 5 nights

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Free cancellation

Guest favourite

Home in Pittsfield Hill

Full Country Home Pittsfield, Illinois

2 bedrooms, 4 beds, No bathroom

16–21 Aug

$567 SGD for 5 nights

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Free cancellation

4.94 out of 5 average rating, 33 reviews