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
Guesthouse in Chester
5.0 out of 5 average rating, 41 reviewsDelightful Cottage in Charming Chester
Oct 18 – 25
R4,181 ZAR per night
Guest favorite
Home in Haddam
5.0 out of 5 average rating, 76 reviewsCozy Comforts!
Dec 14 – 21
R2,073 ZAR per night
Guest favorite
Apartment in Chester
4.99 out of 5 average rating, 70 reviewsThe Millhouse Downtown Chester
Dec 17 – 24
R5,372 ZAR per night
Guest favorite
Apartment in Clinton
4.98 out of 5 average rating, 49 reviewsCozy Shoreline Getaway
Mar 5 – 12
R2,498 ZAR per night
Guest favorite
Guesthouse in Madison
4.93 out of 5 average rating, 14 reviewsIn-law apartment with Private entrance
Nov 5 – 12
R2,280 ZAR per night
Guest favorite
Guest suite in Old Saybrook
5.0 out of 5 average rating, 37 reviewsCozy Loft Getaway
May 6 – 13
R3,014 ZAR per night
Guest favorite
Home in Chester
4.98 out of 5 average rating, 50 reviewsTuscan Villa in Chester
May 6 – 13
R10,119 ZAR per night
Guest favorite
Guesthouse in Madison
5.0 out of 5 average rating, 58 reviewsThe Barn by the Sound
Dec 17 – 24
R3,184 ZAR per night
Quick stats about vacation rentals in Chester
Total rentals
10 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
10 properties include access to wifi
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
2K reviews
Nightly prices starting at
R1,923 ZAR before taxes and fees
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