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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

$724 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

16–21 Aug

$770 SGD for 5 nights

Free cancellation

4.92 out of 5 average rating, 182 reviews

Flat in Winchester

The Primrose inside historic commercial bldg

2 bedrooms, 3 beds, 1 bathroom

7–12 Aug

$877 SGD for 5 nights

4.96 out of 5 average rating, 73 reviews

Home in Winchester

Charming Country Retreat

4 bedrooms, 5 beds, 1 bathroom

2–7 Aug

$1,791 SGD for 5 nights

Free cancellation

New place to stay

Guest favourite

Flat in Winchester

Sugar Shack, a retro studio apartment

1 bedroom, 1 queen bed, 1 bathroom

5–10 Aug

$823 SGD for 5 nights

Free cancellation

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

1–6 Aug

$678 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 408 reviews

Home in Alsey

Douglas Street Retreat

4 bedrooms, 5 beds, 2.5 bathrooms

3–8 Aug

$1,006 SGD for 5 nights

4.8 out of 5 average rating, 15 reviews

Top guest favourite

Cabin in Jacksonville

Audrey's Abode

2 bedrooms, 4 beds, 1 bathroom

4–9 Oct

$983 SGD for 5 nights

Free cancellation

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

$854 SGD for 5 nights

4.92 out of 5 average rating, 106 reviews

Top guest favourite

Loft in Virginia

Two Doors Down Loft, Virginia-Lincoln territory!

2 queen beds, 1.5 bathrooms

11–16 Aug

$485 SGD for 5 nights

Free cancellation

4.95 out of 5 average rating, 210 reviews

Room in Pittsfield

Boutique Queen Suite I Private Bath + Fast WiFi

1 bed, 1.5 bathrooms

16–21 Aug

Free cancellation

New place to stay

Guest favourite

Home in Pittsfield Hill

Full Country Home Pittsfield, Illinois

2 bedrooms, 4 beds, No bathroom

9–14 Aug

$572 SGD for 5 nights

4.94 out of 5 average rating, 32 reviews

Guest favourite

Flat in Pittsfield

Pike County Haven: Retro Loft

1 bedroom, 2 beds, 1 bathroom

9–14 Aug

$873 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 21 reviews

Guest favourite

Home in White Hall

Cozy-Rose-Cottage

2 bedrooms, 3 beds, 1 bathroom

3–8 Aug

$826 SGD for 5 nights

4.92 out of 5 average rating, 88 reviews

Guest favourite

Home in Roodhouse

Cozy Corner Bungalow

2 bedrooms, 4 beds, 1 bathroom

2–7 Aug

$826 SGD for 5 nights

4.92 out of 5 average rating, 39 reviews

Guest favourite

Home in Beardstown

Nostalgia on 5th St

4 bedrooms, 6 beds, 2 bathrooms

2–7 Aug

$1,299 SGD for 5 nights

Free cancellation

4.89 out of 5 average rating, 37 reviews

Top guest favourite

Home in Beardstown

House of Blessings

2 bedrooms, 3 beds, 1 bathroom

2–7 Aug

$925 SGD for 5 nights

4.99 out of 5 average rating, 91 reviews

Guest favourite

Cottage in Pearl

Beautiful Secluded Home With a breathtaking view

3 bedrooms, 5 beds, 2 bathrooms

9–14 Aug

$1,341 SGD for 5 nights

4.96 out of 5 average rating, 97 reviews

Guest favourite

Hotel in Jacksonville

Charming downtown hotel above wine bar - Room 3

1 bedroom, 1 bed, 1 bathroom

1–6 Aug

$1,028 SGD for 5 nights

Free cancellation

4.94 out of 5 average rating, 107 reviews