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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.

Home in Chester
Lakeside Oasis on Brant Lake
Cozy, stylish, and fully furnished lake front home with breathtaking views of Brant Lake that is perfect for your next getaway! Whether you are enjoying the sunrise on the back patio with a cup of coffee, playing yard games along the 112 feet of shoreline, roasting marshmallows around the fire pit, or fishing off the dock, you are sure to have a relaxing time! Utilize the private on-site ramp to drop your jet ski’s in the water, use your water toys, or go for a dip.
$249 per night
Cabin in Wentworth
Immaculate Year-Round Lake Madison home
This property features the main home (3 bed, 2 baths). You can rent the guest house (pictured on the right) as well; please inquire. This property offers spectacular views of Lake Madison from the south shore. The screen porch access from inside the home and to the lake. This place is immaculate and will need to be well-cared for by guests. This is a new listing for us; we are Superhosts and have more than 600 positive reviews. We look forward to hosting you!
$195 per night
Cabin in Wentworth
Intimate lake-side cabin with cozy outdoor space
Relax in this newly renovated, modern cabin. An easy 40 minutes from Sioux Falls, its truly lakeside location lets you wake up to the sound of crashing waves just outside your bedroom window. Enjoy a peaceful morning with coffee on the deck, then explore the lake via kayak, and finish your day by cozying up to a romantic fire under the gazebo. Perfect for a quiet couple’s getaway. (Note: the bunk beds are only suitable for children)
$200 per night

Other great vacation rentals in Chester

Cabin in Madison
Salty Pirate Cabin on Lake Madison
$164 per night
Loft in Flandreau
Bend In the River AirBnB
$74 per night
Cabin in Wentworth
Lake Madison Cabin
$164 per night
Condo in Wentworth
Fun Condo with Lakeview
$194 per night
Home in Madison
Charming 4-Square Built In 1889
$98 per night
Guesthouse in Sioux Falls
The Chic Suite | Sleeps 3 | Dogs Welcome
$92 per night
Treehouse in Valley Springs
Lookout Loft Treehouse
$144 per night
Rental unit in Sioux Falls
The Elephant Suite
$60 per night
Private room in Wentworth
#20 Lakes Lodge - Charming 1 Room Suite (Handicap)
$95 per night
Rental unit in Flandreau
Hansen’s Hometown Hideaway
$65 per night
Home in Salem
The Cottage in Salem
$85 per night
Guest suite in Brookings
Shamrock Suite
$92 per night
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  2. United States
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  5. Chester