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Search results; 153 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

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

Home in Winchester

Charming Country Retreat

4 bedrooms, 5 beds, 1 bathroom

2–7 Aug

$1,776 SGD for 5 nights

New place to stay

Guest favourite

Guest suite in Pittsfield

Florence Guest House--Loft Unit

1 bedroom, 3 beds, 1 bathroom

23–28 Aug

$481 SGD for 5 nights

4.82 out of 5 average rating, 139 reviews

Room in Pittsfield

Premium King Suite | Boutique Stay + Private Bath

1 bed, 1 bathroom

9–14 Aug

$642 SGD for 5 nights

4.8 out of 5 average rating, 5 reviews

Top guest favourite

Flat in Murrayville

Peace on the Prairie - Studio Apartment

1 bedroom, 4 beds, 1 bathroom

1–6 Sept

$686 SGD for 5 nights

4.97 out of 5 average rating, 432 reviews

Guest favourite

Flat in Pittsfield

Pike County Haven: Retro Loft

1 bedroom, 2 beds, 1 bathroom

9–14 Aug

$866 SGD for 5 nights

5.0 out of 5 average rating, 21 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

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

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

Guest favourite

Rooms in Pittsfield

Sloth Lodging (Upper Level)

3 bedrooms, 3 beds, 1 bathroom

1–6 Aug

$545 SGD for 5 nights

4.91 out of 5 average rating, 54 reviews

Room in Pittsfield

Quiet Queen Suite | Boutique Comfort, Private Bath

1 bed, 1.5 bathrooms

9–14 Aug

New place to stay

Flat in Jacksonville

Baker & Birch

2 bedrooms, 3 beds, 1 bathroom

9–14 Aug

$1,379 SGD for 5 nights

New place to stay