Vacation rentals in Chester
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Top-rated vacation rentals in Chester
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chester vacation rentals
Other great vacation rentals in Chester
Guest favorite
Cabin in Wentworth
5.0 out of 5 average rating, 34 reviewsIntimate lake-side cabin with cozy outdoor space
Mar 18 – 25
ﺩ.ﺇ899 per night
Superhost
Home in Chester
4.87 out of 5 average rating, 45 reviewsLakeside Oasis on Brant Lake
Oct 4 – 11
ﺩ.ﺇ1,052 per night
Guest favorite
Cabin in Wentworth
4.79 out of 5 average rating, 66 reviewsLake Madison Cabin
Sep 15 – 22
ﺩ.ﺇ661 per night
Guest favorite
Home in Emery
4.97 out of 5 average rating, 34 reviewsSunset Cottage
Feb 20 – 27
ﺩ.ﺇ400 per night
Guest favorite
Home in Madison
4.93 out of 5 average rating, 30 reviewsWATERFRONT HOME ON LAKE MADISON
May 28 – Jun 4
ﺩ.ﺇ1,217 per night
Guest favorite
Home in Flandreau
5.0 out of 5 average rating, 14 reviewsWillow Run Townhome
Feb 23 – Mar 2
ﺩ.ﺇ458 per night
Guest favorite
Home in Madison
5.0 out of 5 average rating, 8 reviewsAmazing Madison House near DSU
Sep 28 – Oct 5
ﺩ.ﺇ754 per night
Guest favorite
Home in Madison
4.99 out of 5 average rating, 67 reviewsBlack Bear Lodge Lake Madison
Sep 17 – 24
ﺩ.ﺇ1,798 per night
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