We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Search results; Over 1,000 homes in Winchester

Guest favourite

Home in Winchester

City Charmer minutes from Old Town

2 bedrooms, 2 beds, 1 private bathroom

11–16 Aug

$936 SGD for 5 nights

,

4.97 out of 5 average rating, 285 reviews

Top guest favourite

Cottage in Winchester

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

1 bedroom, 1 queen bed, 1 bathroom

13–18 Jul

$1,493 SGD for 5 nights

4.99 out of 5 average rating, 475 reviews

Top guest favourite

Flat in Winchester

Downtowner

2 bedrooms, 3 beds, 1 bathroom

11–16 Jul

$1,055 SGD for 5 nights

4.97 out of 5 average rating, 349 reviews

Top guest favourite

Flat in Winchester

Downtown FUN! Personal Mid Century 2bd Apartment!

2 bedrooms, 2 queen beds, 1 bathroom

12–17 Jul

$953 SGD for 5 nights

4.9 out of 5 average rating, 267 reviews

Top guest favourite

Home in Winchester

Skyview Farmhouse

3 bedrooms, 5 beds, 2 bathrooms

12–17 Jul

$1,356 SGD for 5 nights

4.98 out of 5 average rating, 50 reviews

Guest favourite

Flat in Winchester

Cozy & Charming Downtown Apartment

1 bedroom, 1 bed, 1 bathroom

1–6 Jul

$1,321 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 7 reviews

Guest favourite

Flat in Winchester

Scarborough Fair walk to downtown two story apt

3 bedrooms, 6 beds, 1 bathroom

5–10 Jul

4.9 out of 5 average rating, 138 reviews

Top guest favourite

Room in Winchester

Winchester Private Room

1 queen bed, 1 bathroom

6–11 Jul

$459 SGD for 5 nights

4.99 out of 5 average rating, 187 reviews

Top guest favourite

Home in Winchester

Cameron Charmer pristine w/double master suites

2 bedrooms, 2 queen beds, 2.5 bathrooms

1–6 Jul

$1,560 SGD for 5 nights

4.98 out of 5 average rating, 220 reviews

Top guest favourite

Home in Winchester

Colonial Getaway Near Old Town Historic Winchester

3 bedrooms, 4 beds, 2.5 bathrooms

1–6 Aug

$1,230 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 241 reviews

Cabin in Winchester

Mountain Retreat | Sauna, Hot Tub & Views Near DC

1 bedroom, 2 beds, 1 bathroom

5–10 Jul

$1,804 SGD for 5 nights

New place to stay

Top guest favourite

Home in Winchester

Aunt Tim's Farmhouse

5 bedrooms, 6 beds, 1.5 bathrooms

26–31 Jul

$1,338 SGD for 5 nights

Free cancellation

4.96 out of 5 average rating, 155 reviews

Guest favourite

Home in Clear Brook

Cedar Hill Cottage- 3 mi to I-81 & Rt 11

2 bedrooms, 2 queen beds, 1.5 bathrooms

12–17 Jul

$889 SGD for 5 nights

4.93 out of 5 average rating, 44 reviews

Top guest favourite

Room in Winchester

We Welcome You to Winchester! Best reviews!

1 double bed, 1.5 bathrooms

1–6 Jul

$620 SGD for 5 nights

4.93 out of 5 average rating, 239 reviews

Top guest favourite

Home in Martinsburg

Architectural Mountaintop Retreat | Shenandoah

4 bedrooms, 5 beds, 3 bathrooms

5–10 Jul

$3,022 SGD for 5 nights

5.0 out of 5 average rating, 21 reviews

Guest favourite

Cabin in Stephens City

Chalet w/Hot Tub, Deck, Game Room & EV Charger

3 bedrooms, 3 beds, 2 bathrooms

14–19 Jul

$2,514 SGD for 5 nights

4.83 out of 5 average rating, 18 reviews

Hotel room in Winchester

George Washington l Queen Bed l Historic Charm

1 bedroom, 1 queen bed, 1 bathroom

1–6 Jul

$1,096 SGD for 5 nights

Guest favourite

Home in Millwood

Peony Place renovated farmhouse in horse country

2 bedrooms, 2 beds, 1 bathroom

5–10 Jul

$1,751 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

Guest favourite

Home in Winchester

Historic District Charm On Cameron Street

3 bedrooms, 3 beds, 1.5 bathrooms

1–6 Jul

$1,185 SGD for 5 nights

4.92 out of 5 average rating, 173 reviews