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Winchester
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119 places in Winchester
Guest favorite
Guest favorite
Home in Winchester
Winchester Guest Cottage
2 beds
2 beds
May 5 – 10
May 5 – 10
$89
night
$89 per night
4.93 out of 5 average rating, 43 reviews
4.93 (43)
Guest favorite
Guest favorite
Loft in Winchester
The Bike Flat
5 beds
5 beds
Apr 14 – 19
Apr 14 – 19
$94
night
$94 per night
4.97 out of 5 average rating, 77 reviews
4.97 (77)
Guest favorite
Guest favorite
Apartment in Winchester
Sugar Shack, a retro studio apartment
1 queen bed
1 queen bed
Apr 1 – 6
Apr 1 – 6
$100
night
$100 per night
4.88 out of 5 average rating, 40 reviews
4.88 (40)
Guest favorite
Guest favorite
Cabin in Jacksonville
Audrey's Abode
4 beds
4 beds
Apr 8 – 13
Apr 8 – 13
$129
night
$129 per night
4.97 out of 5 average rating, 614 reviews
4.97 (614)
Guest favorite
Guest favorite
Cabin in Jacksonville
Bunkhouse Seventy-Four
1 queen bed
1 queen bed
Apr 9 – 14
Apr 9 – 14
$89
night
$89 per night
4.97 out of 5 average rating, 271 reviews
4.97 (271)
Guest favorite
Guest favorite
Apartment in Winchester
The Primrose inside historic commercial bldg
3 beds
3 beds
May 1 – 6
May 1 – 6
$100
night
$100 per night
4.97 out of 5 average rating, 67 reviews
4.97 (67)
Guest favorite
Guest favorite
Vacation home in Meredosia
Scenic 3 bedroom Wildlife Retreat
5 beds
5 beds
Apr 1 – 6
Apr 1 – 6
$95
night
$95 per night
4.96 out of 5 average rating, 55 reviews
4.96 (55)
Guest favorite
Guest favorite
Home in Griggsville
Arrowhead Farmhouse, Spacious home, scenic views
6 beds
6 beds
Apr 1 – 6
Apr 1 – 6
$219
night
$219 per night
4.88 out of 5 average rating, 76 reviews
4.88 (76)
Guest favorite
Guest favorite
Apartment in Murrayville
Peace on the Prairie - Studio Apartment
4 beds
4 beds
Apr 1 – 6
Apr 1 – 6
$95
$86
night
$86 per night, originally $95
4.97 out of 5 average rating, 381 reviews
4.97 (381)
Guest favorite
Guest favorite
Cottage in Pearl
Beautiful Secluded Home With a breathtaking view
5 beds
5 beds
Apr 9 – 14
Apr 9 – 14
$188
night
$188 per night
4.98 out of 5 average rating, 66 reviews
4.98 (66)
Guest favorite
Guest favorite
Townhouse in Murrayville
Peace on the Prairie Too - Tiny House
3 beds
3 beds
Apr 9 – 14
Apr 9 – 14
$98
$88
night
$88 per night, originally $98
4.98 out of 5 average rating, 262 reviews
4.98 (262)
Guest favorite
Guest favorite
Home in Beardstown
My Little Bungalow on Monroe Street.
5 beds
5 beds
Apr 2 – 7
Apr 2 – 7
$97
night
$97 per night
4.99 out of 5 average rating, 155 reviews
4.99 (155)
Guest favorite
Guest favorite
Home in Jacksonville
1.5 bath,laundry,DW,Netflix,HS Wi-Fi,deck,ext.stay
2 beds
2 beds
Apr 1 – 6
Apr 1 – 6
$129
night
$129 per night
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Guest favorite
Guest favorite
Home in Pittsfield
Newly remodeled home
2 queen beds
2 queen beds
Apr 1 – 6
Apr 1 – 6
$129
night
$129 per night
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Guest favorite
Guest favorite
Home in White Hall
Cozy-Rose-Cottage
3 beds
3 beds
Apr 1 – 6
Apr 1 – 6
$85
night
$85 per night
4.95 out of 5 average rating, 20 reviews
4.95 (20)
Home in Roodhouse
Cozy Corner Bungalow
4 beds
4 beds
Apr 1 – 6
Apr 1 – 6
$85
night
$85 per night
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Guest favorite
Guest favorite
Home in Pittsfield
Florence Guest House
5 beds
5 beds
Apr 1 – 6
Apr 1 – 6
$49
night
$49 per night
4.83 out of 5 average rating, 201 reviews
4.83 (201)
Superhost
Superhost
Guest suite in Pittsfield
Florence Guest House--Loft Unit
3 beds
3 beds
Apr 1 – 6
Apr 1 – 6
$49
night
$49 per night
4.8 out of 5 average rating, 115 reviews
4.8 (115)
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