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Search results; 141 homes in Winchester

Top guest favourite

Cabin in Winchester

Container Home GREAT Countryside Views COZY Stay

1 bedroom, 1 bed, 1 private bathroom

24–29 Aug

$719 SGD for 5 nights

,

4.96 out of 5 average rating, 196 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

Home in Winchester

Charming Country Retreat

4 bedrooms, 5 beds, 1 bathroom

9–14 Aug

$1,778 SGD for 5 nights

New place to stay

Flat in Winchester

The Primrose inside historic commercial bldg

2 bedrooms, 3 beds, 1 bathroom

11–16 Aug

$870 SGD for 5 nights

4.93 out of 5 average rating, 75 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

24–29 Aug

$674 SGD for 5 nights

4.98 out of 5 average rating, 410 reviews

Top guest favourite

Cabin in Jacksonville

Audrey's Abode

2 bedrooms, 4 beds, 1 bathroom

4–9 Oct

$976 SGD for 5 nights

4.97 out of 5 average rating, 781 reviews

Guest favourite

Home in White Hall

The Humble Hideaway

3 bedrooms, 3 beds, 2 bathrooms

9–14 Aug

$848 SGD for 5 nights

4.91 out of 5 average rating, 107 reviews

Top guest favourite

Loft in Virginia

Two Doors Down Loft, Virginia-Lincoln territory!

2 queen beds, 1.5 bathrooms

1–6 Sept

$482 SGD for 5 nights

4.95 out of 5 average rating, 212 reviews

Top guest favourite

Flat in Murrayville

Peace on the Prairie - Studio Apartment

1 bedroom, 4 beds, 1 bathroom

1–6 Sept

$687 SGD for 5 nights

4.97 out of 5 average rating, 432 reviews

Guest favourite

Guest suite in Pittsfield

Florence Guest House--Loft Unit

1 bedroom, 3 beds, 1 bathroom

29 Aug – 3 Sept

$482 SGD for 5 nights

4.82 out of 5 average rating, 139 reviews

Home in Alsey

Douglas Street Retreat

4 bedrooms, 5 beds, 2.5 bathrooms

13–18 Sept

$977 SGD for 5 nights

4.8 out of 5 average rating, 15 reviews

Home in Pittsfield

Newly remodeled home

2 bedrooms, 2 queen beds, 1 bathroom

9–14 Aug

4.87 out of 5 average rating, 55 reviews

Top guest favourite

Flat in Beardstown

The VanderWaal

2 bedrooms, 2 beds, 1 bathroom

17–22 Aug

$1,324 SGD for 5 nights

5.0 out of 5 average rating, 27 reviews

Hotel room in Jacksonville

2 Queen Beds | Super 8 Jacksonville | Family Stay

1 bedroom, 2 queen beds, 1 bathroom

7–12 Aug

$447 SGD for 5 nights

Top guest favourite

Home in Mount Sterling

Cozy Cottage 405

2 bedrooms, 2 queen beds, 1 bathroom

12–17 Aug

$1,014 SGD for 5 nights

4.94 out of 5 average rating, 17 reviews

Top guest favourite

Holiday home in Meredosia

Scenic 3 bedroom Wildlife Retreat

3 bedrooms, 5 beds, 1 bathroom

12–17 Aug

$868 SGD for 5 nights

4.98 out of 5 average rating, 97 reviews

Guest favourite

Home in Pittsfield

Florence Guest House

3 bedrooms, 5 beds, 2 bathrooms

17–22 Sept

$463 SGD for 5 nights

4.84 out of 5 average rating, 256 reviews

Guest favourite

Hotel in Jacksonville

Charming downtown hotel above wine bar - Room 3

1 bedroom, 1 bed, 1 bathroom

9–14 Aug

$993 SGD for 5 nights

4.94 out of 5 average rating, 109 reviews