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Search results; 138 homes in Winchester

Top guest favourite

Cabin in Winchester

Container Home GREAT Countryside Views COZY Stay

1 bedroom, 1 bed, 1 private bathroom

2–7 Aug

$718 SGD for 5 nights

,

4.96 out of 5 average rating, 194 reviews

Guest favourite

Loft in Winchester

The Bike Flat

2 bedrooms, 5 beds, 1 bathroom

23–28 Aug

$765 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, 1 bathroom

7–12 Aug

$869 SGD for 5 nights

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

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

$817 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

7–12 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, 1 bathroom

18–23 Aug

$975 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, 2 bathrooms

9–14 Aug

$847 SGD for 5 nights

4.92 out of 5 average rating, 106 reviews

Home in Alsey

Douglas Street Retreat

4 bedrooms, 5 beds, 2.5 bathrooms

13–18 Sept

$976 SGD for 5 nights

4.8 out of 5 average rating, 15 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

4.98 out of 5 average rating, 61 reviews

Superhost

Cabin in Hillview

Modern-Rustic Cabin, Nature Inspired

2 beds, 1 bathroom

4–9 Aug

Extended stay discount

4.86 out of 5 average rating, 49 reviews

Top guest favourite

Loft in Virginia

Two Doors Down Loft, Virginia-Lincoln territory!

2 queen beds, 1.5 bathrooms

25–30 Aug

$481 SGD for 5 nights

4.95 out of 5 average rating, 211 reviews

Guest favourite

Loft in Pittsfield

Historic Loft on Adams

1 bedroom, 1 bed, 1 bathroom

9–14 Aug

$565 SGD for 5 nights

4.91 out of 5 average rating, 95 reviews

Flat in Carrollton

Farmhouse Loft

2 bedrooms, 3 beds, 1 bathroom

30 Aug – 4 Sept

$643 SGD for 5 nights

4.85 out of 5 average rating, 191 reviews

Guest favourite

Cottage in Pearl

Beautiful Secluded Home With a breathtaking view

3 bedrooms, 5 beds, 2 bathrooms

9–14 Aug

$1,330 SGD for 5 nights

4.96 out of 5 average rating, 97 reviews

Guest favourite

Home in White Hall

Cozy-Rose-Cottage

2 bedrooms, 3 beds, 1 bathroom

3–8 Aug

$820 SGD for 5 nights

4.92 out of 5 average rating, 88 reviews

Top guest favourite

Holiday home in Meredosia

Scenic 3 bedroom Wildlife Retreat

3 bedrooms, 5 beds, 1 bathroom

12–17 Aug

$867 SGD for 5 nights

4.98 out of 5 average rating, 97 reviews

Top guest favourite

Cottage in Beardstown

The Jungle Farm Country Quiet, Town Convenient

3 bedrooms, 4 beds, 2 bathrooms

6–11 Dec

$1,103 SGD for 5 nights

4.94 out of 5 average rating, 77 reviews

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

4.94 out of 5 average rating, 32 reviews