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Search results; Over 1,000 homes in Winchester

Top guest favourite

Home in Winchester

Aunt Tim's Farmhouse

5 bedrooms, 6 beds, 1.5 private bathrooms

29 Aug – 3 Sept

$1,334 SGD for 5 nights

,

4.96 out of 5 average rating, 159 reviews

Top guest favourite

Flat in Winchester

Downtowner

2 bedrooms, 3 beds

2–7 Aug

$1,007 SGD for 5 nights

4.97 out of 5 average rating, 354 reviews

Top guest favourite

Flat in Winchester

Downtown FUN! Personal Mid Century 2bd Apartment!

2 bedrooms, 2 queen beds

9–14 Aug

$1,030 SGD for 5 nights

4.91 out of 5 average rating, 274 reviews

Top guest favourite

Cottage in Winchester

COZY+SEXY Private Country Escape! HOT TUB & Views~

1 bedroom, 1 queen bed

16–21 Aug

$1,364 SGD for 5 nights

4.99 out of 5 average rating, 483 reviews

Top guest favourite

Room in Winchester

Winchester Private Room

1 queen bed

9–14 Aug

$458 SGD for 5 nights

4.99 out of 5 average rating, 192 reviews

Top guest favourite

Home in Winchester

Cameron Charmer pristine w/double master suites

2 bedrooms, 2 queen beds

2–7 Aug

$1,494 SGD for 5 nights

4.98 out of 5 average rating, 221 reviews

Top guest favourite

Home in Winchester

Colonial Getaway Near Old Town Historic Winchester

3 bedrooms, 4 beds

4–9 Sept

$1,242 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 246 reviews

Guest favourite

Flat in Winchester

Scarborough Fair walk to downtown two story apt

3 bedrooms, 6 beds

2–7 Aug

$1,762 SGD for 5 nights

4.9 out of 5 average rating, 143 reviews

Top guest favourite

Guest suite in Winchester

Retro Vibe Studio

1 queen bed

12–17 Oct

$710 SGD for 5 nights

4.94 out of 5 average rating, 66 reviews

Guest favourite

Home in Winchester

Historic District Charm On Cameron Street

3 bedrooms, 3 beds

10–15 Aug

$1,181 SGD for 5 nights

4.92 out of 5 average rating, 175 reviews

Top guest favourite

Flat in Winchester

Peaceful Family Retreat in the Heart of Winchester

1 bedroom, 3 beds

16–21 Aug

$729 SGD for 5 nights

5.0 out of 5 average rating, 76 reviews

Top guest favourite

Cottage in Berryville

Milton Valley Cottage on Historic Estate Farm

2 bedrooms, 2 beds

4–9 Aug

$1,205 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 120 reviews

Guest favourite

Flat in Winchester

Cameron Loft 2 Story Studio with 1.5 Bath Downtown

1 bedroom, 1 double bed

1–6 Aug

$1,007 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Guest favourite

Home in Winchester

Springdale Mill Farmhouse with Spa House

4 bedrooms, 5 beds

1–6 Aug

$2,100 SGD for 5 nights

Free cancellation

4.87 out of 5 average rating, 91 reviews

Top guest favourite

Home in Winchester

Skyview Farmhouse

3 bedrooms, 5 beds

1–6 Aug

$2,217 SGD for 5 nights

4.98 out of 5 average rating, 55 reviews

Hotel room in Winchester

George Washington l Queen Bed l Historic Charm

1 bedroom, 1 queen bed

1–6 Aug

$994 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in Winchester

Downtown Chic Condo w/parking

1 bedroom

1–6 Aug

$1,245 SGD for 5 nights

5.0 out of 5 average rating, 88 reviews

Top guest favourite

Guest suite in Clear Brook

Bluebird Bungalow

1 bedroom, 3 beds

3–8 Aug

$937 SGD for 5 nights

4.97 out of 5 average rating, 73 reviews

Top guest favourite

Flat in Winchester

Historic French Modern Downtown

2 bedrooms, 2 beds

17–24 Aug

$1,220 SGD for 7 nights

4.95 out of 5 average rating, 40 reviews