Chester Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Chester

Beautiful year round lake home! Sleeps 8 comfortably!

Lake View Township SD

Located in Madison, this vacation home is on the waterfront, a 1-minute drive from Lake Madison and 5 minutes from Madison Regional Health System.

3+ night special | King Bed | Dog friendly + Fenced Yard | 3 TVs

Madison SD

With a stay at this vacation home in Madison, you'll be next to a golf course, just a 4-minute walk from Baughman Park and 5 minutes by foot from Totland Park.

Skeet’s Retreat: Lake Herman Lakefront Getaway Near Madison, SD - Sleeps 8

Madison SD

Located in Madison, this vacation home is on the waterfront, within a 5-minute drive of Lake Herman State Park and Prairie Village.

Kitchen

Washer

Unique Home Where The Buffalo Roam! Perfect for Families, Reunions. Hunters.

Buffalo Ridge SD

When you stay at this vacation home in Sioux Falls, you'll be on a river, within a 15-minute drive of Denny Sanford Premier Center and Falls Park.

Kitchen

Washer

Lakeside Getaway on Lake Madison. Hot tub with a view of the lake!

Wentworth SD

Located in Wentworth, this vacation home is on the waterfront, a 1-minute drive from Lake Madison and 9 minutes from Lakes Golf Course.

Hot Tub

Kitchen

4-bedroom 3 bath lakefront home on Brandt Lake

Chester SD

Located in Chester, this vacation home is within a 15-minute drive of Lake Madison and Lakes Golf Course.

Kitchen

Washer

Don't see what you're looking for?

See all available properties in Chester

View all properties

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.