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Search results; Over 1,000 homes in Winchester

Top guest favourite

Cottage in Winchester

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

1 bedroom, 1 queen bed

16–21 Aug

$1,361 SGD for 5 nights

4.99 out of 5 average rating, 481 reviews

Top guest favourite

Flat in Winchester

Downtowner

2 bedrooms, 3 beds

2–7 Aug

$1,006 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 354 reviews

Top guest favourite

Flat in Winchester

Old Town Modern Twist! Rock n’ Roll FUN w/Parking!

2 bedrooms, 2 beds

15–20 Aug

$961 SGD for 5 nights

4.95 out of 5 average rating, 203 reviews

Top guest favourite

Room in Winchester

Winchester Private Room

1 queen bed

3–8 Aug

$457 SGD for 5 nights

Free cancellation

4.99 out of 5 average rating, 191 reviews

Top guest favourite

Home in Winchester

Colonial Getaway Near Old Town Historic Winchester

3 bedrooms, 4 beds

25–30 Aug

$1,262 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 246 reviews

Top guest favourite

Home in Winchester

Cameron Charmer pristine w/double master suites

2 bedrooms, 2 queen beds

2–7 Aug

$1,492 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 221 reviews

Top guest favourite

Cottage in Berryville

Milton Valley Cottage on Historic Estate Farm

2 bedrooms, 2 beds

4–9 Aug

$1,200 SGD for 5 nights

Free cancellation

4.97 out of 5 average rating, 119 reviews

Top guest favourite

Home in Winchester

Aunt Tim's Farmhouse

5 bedrooms, 6 beds

29 Aug – 3 Sept

$1,332 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 159 reviews

Top guest favourite

Home in Winchester

Skyview Farmhouse

3 bedrooms, 5 beds

1–6 Aug

$1,834 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 55 reviews

Guest favourite

Home in Winchester

Winchester farm

3 bedrooms, 3 beds

1–6 Aug

$3,978 SGD for 5 nights

5.0 out of 5 average rating, 13 reviews

Guest favourite

Flat in Winchester

Scarborough Fair walk to downtown two story apt

3 bedrooms, 6 beds

2–7 Aug

$1,804 SGD for 5 nights

Free cancellation

4.9 out of 5 average rating, 142 reviews

Cabin in Winchester

Private Mountain Retreat | Sauna, Hot Tub & Views

1 bedroom, 2 beds

2–7 Aug

$1,744 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Home in Harpers Ferry

Gorgeous cabin on Blue Ridge

2 bedrooms, 2 queen beds

30 Nov – 5 Dec

$1,191 SGD for 5 nights

4.97 out of 5 average rating, 121 reviews

Guest favourite

Home in Winchester

Historic District Charm On Cameron Street

3 bedrooms, 3 beds

10–15 Aug

$1,180 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 175 reviews

Top guest favourite

Cabin in High View

Mary's Cabin

1 bedroom, 4 beds

25–30 Oct

$951 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 204 reviews

Top guest favourite

Home in Winchester

Swim, kayak, fish, and enjoy nature on Back Creek

3 bedrooms, 3 beds

15–20 Aug

$1,743 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 49 reviews

Top guest favourite

Home in Winchester

Springdale Mill Farmhouse with Spa House

4 bedrooms, 5 beds

1–6 Aug

$2,097 SGD for 5 nights

Free cancellation

4.87 out of 5 average rating, 91 reviews

Top guest favourite

Home in Winchester

Bear Drop Inn, walking trails, pond, Winchester

4 bedrooms, 7 beds

1–6 Aug

$3,162 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 24 reviews