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Search results; 154 homes in Winchester

Guest favourite

Loft in Winchester

The Bike Flat

2 bedrooms, 5 beds, 1 private bathroom

22–27 Jul

$785 SGD for 5 nights

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4.93 out of 5 average rating, 175 reviews

Home in Winchester

Charming Country Retreat

4 bedrooms, 5 beds, 1 bathroom

12–17 Jul

New place to stay

Flat in Winchester

The Primrose inside historic commercial bldg

2 bedrooms, 3 beds, 1 bathroom

3–8 Aug

$876 SGD for 5 nights

4.96 out of 5 average rating, 73 reviews

Guest favourite

Flat in Winchester

Sugar Shack, a retro studio apartment

1 bedroom, 1 queen bed, 1 bathroom

20–25 Jul

$823 SGD for 5 nights

4.89 out of 5 average rating, 54 reviews

Top guest favourite

Cabin in Winchester

Container Home GREAT Countryside Views COZY Stay

1 bedroom, 1 king bed, 1 bathroom

19–24 Jul

$724 SGD for 5 nights

4.96 out of 5 average rating, 190 reviews

Guest favourite

Home in Pittsfield

Florence Guest House

3 bedrooms, 5 beds, 2 bathrooms

12–17 Jul

$517 SGD for 5 nights

4.84 out of 5 average rating, 256 reviews

Top guest favourite

Cabin in Jacksonville

Bunkhouse Seventy-Four

1 bedroom, 1 queen bed, 1 bathroom

30 Jul – 4 Aug

$678 SGD for 5 nights

4.98 out of 5 average rating, 403 reviews

Home in Alsey

Douglas Street Retreat

4 bedrooms, 5 beds, 2.5 bathrooms

21–26 Jul

$1,028 SGD for 5 nights

4.77 out of 5 average rating, 13 reviews

Top guest favourite

Cabin in Jacksonville

Audrey's Abode

2 bedrooms, 4 beds, 1 bathroom

4–9 Oct

$983 SGD for 5 nights

4.97 out of 5 average rating, 776 reviews

Guest favourite

Home in White Hall

The Humble Hideaway

3 bedrooms, 3 beds, 2 bathrooms

9–14 Aug

$853 SGD for 5 nights

4.91 out of 5 average rating, 103 reviews

Guest favourite

Guest suite in Pittsfield

Florence Guest House--Loft Unit

1 bedroom, 3 beds, 1 bathroom

12–17 Jul

$485 SGD for 5 nights

4.82 out of 5 average rating, 139 reviews

Guest favourite

Home in Roodhouse

Cozy Corner Bungalow

2 bedrooms, 4 beds, 1 bathroom

12–17 Jul

$846 SGD for 5 nights

4.92 out of 5 average rating, 38 reviews

Top guest favourite

Home in White Hall

Cozy-Rose-Cottage

2 bedrooms, 3 beds, 1 bathroom

14–19 Jul

$846 SGD for 5 nights

4.92 out of 5 average rating, 87 reviews

Guest favourite

Home in Jacksonville

Rees Residential

2 bedrooms, 3 beds, 1 bathroom

13–18 Jul

$1,432 SGD for 5 nights

4.85 out of 5 average rating, 46 reviews

Flat in Jacksonville

Baker & Birch

2 bedrooms, 3 beds, 1 bathroom

12–17 Jul

$1,389 SGD for 5 nights

New place to stay

Guest favourite

Cottage in Pearl

Beautiful Secluded Home With a breathtaking view

3 bedrooms, 5 beds, 2 bathrooms

12–17 Jul

$1,341 SGD for 5 nights

4.96 out of 5 average rating, 96 reviews

Home in Mount Sterling

Idyllic Mt Sterling Retreat w/ Private Lake!

4 bedrooms, 13 beds, 2.5 bathrooms

18–23 Aug

$1,981 SGD for 5 nights

4.84 out of 5 average rating, 32 reviews

Top guest favourite

Barn in Jacksonville

Basketball Pickleball +Party Room + Loft Sleeps 17

2 bedrooms, 16 beds, 1.5 bathrooms

13–18 Jul

4.97 out of 5 average rating, 97 reviews

Top guest favourite

Cabin in Kampsville

Exotic Animal Farm Stay in Illinois: Tour, Explore

1 bedroom, 3 queen beds, 1 bathroom

19–24 Jul

$1,325 SGD for 5 nights

5.0 out of 5 average rating, 19 reviews