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Search results; 153 homes in Winchester

Guest favourite

Loft in Winchester

The Bike Flat

2 bedrooms, 5 beds, 1 private bathroom

22–27 Jul

$770 SGD for 5 nights

,

4.92 out of 5 average rating, 177 reviews

Home in Winchester

Charming Country Retreat

4 bedrooms, 5 beds

17–22 Jul

$1,864 SGD for 5 nights

New place to stay

Guest favourite

Flat in Winchester

Sugar Shack, a retro studio apartment

1 bedroom, 1 queen bed

20–25 Jul

$822 SGD for 5 nights

4.89 out of 5 average rating, 54 reviews

Flat in Winchester

The Primrose inside historic commercial bldg

2 bedrooms, 3 beds

3–8 Aug

$875 SGD for 5 nights

4.96 out of 5 average rating, 73 reviews

Top guest favourite

Cabin in Winchester

Container Home GREAT Countryside Views COZY Stay

1 bedroom, 1 king bed

19–24 Jul

$723 SGD for 5 nights

4.96 out of 5 average rating, 191 reviews

Top guest favourite

Cabin in Jacksonville

Bunkhouse Seventy-Four

1 bedroom, 1 queen bed

7–12 Aug

$678 SGD for 5 nights

4.98 out of 5 average rating, 404 reviews

Guest favourite

Home in Pittsfield

Florence Guest House

3 bedrooms, 5 beds

16–21 Jul

$517 SGD for 5 nights

4.84 out of 5 average rating, 256 reviews

Top guest favourite

Cabin in Jacksonville

Audrey's Abode

2 bedrooms, 4 beds

4–9 Oct

$982 SGD for 5 nights

4.97 out of 5 average rating, 777 reviews

Guest favourite

Home in White Hall

Cozy-Rose-Cottage

2 bedrooms, 3 beds

16–21 Jul

$845 SGD for 5 nights

4.92 out of 5 average rating, 87 reviews

Home in Alsey

Douglas Street Retreat

4 bedrooms, 5 beds

21–26 Jul

$1,027 SGD for 5 nights

4.79 out of 5 average rating, 14 reviews

Top guest favourite

Home in Pittsfield

Spacious whole house in Pittsfield!

3 bedrooms, 5 beds

17–22 Jul

5.0 out of 5 average rating, 7 reviews

Guest favourite

Guest suite in Pittsfield

Florence Guest House--Loft Unit

1 bedroom, 3 beds

15–20 Jul

$485 SGD for 5 nights

4.82 out of 5 average rating, 139 reviews

Top guest favourite

Home in Beardstown

My Little Bungalow on Monroe Street.

2 bedrooms, 5 beds

2–7 Aug

$718 SGD for 5 nights

4.98 out of 5 average rating, 319 reviews

Guest favourite

Home in White Hall

The Humble Hideaway

3 bedrooms, 3 beds

9–14 Aug

$852 SGD for 5 nights

4.91 out of 5 average rating, 104 reviews

Top guest favourite

Flat in Murrayville

Peace on the Prairie - Studio Apartment

1 bedroom, 4 beds

19–24 Jul

$694 SGD for 5 nights

4.97 out of 5 average rating, 429 reviews

Guest favourite

Hotel in Jacksonville

Charming downtown hotel above wine bar - Room 3

1 bedroom, 1 bed

18–23 Jul

$1,034 SGD for 5 nights

4.94 out of 5 average rating, 106 reviews

Guest favourite

Home in Roodhouse

Cozy Corner Bungalow

2 bedrooms, 4 beds

20–25 Jul

$845 SGD for 5 nights

4.92 out of 5 average rating, 39 reviews

Guest favourite

Home in Pittsfield Hill

Full Country Home Pittsfield, Illinois

2 bedrooms, 4 beds

19–24 Jul

$571 SGD for 5 nights

4.94 out of 5 average rating, 31 reviews

Guest favourite

Cottage in Pearl

Beautiful Secluded Home With a breathtaking view

3 bedrooms, 5 beds

16–21 Jul

$1,400 SGD for 5 nights

4.96 out of 5 average rating, 96 reviews