Chester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Find vacation rentals that suit your style

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Top Chester Hotel Reviews

A Best Western PLUS hotel with a modern design, featuring a covered entrance and multiple floors.
Best Western Plus Lakeview Hotel

Best Western Plus Lakeview Hotel

Best Western Plus Lakeview Hotel
Madison

10/10 Excellent

The stay at this facility was great. The accomodations, service and staff were 5 star ratings for our stay. Our family will always choose this property for you visits to Madison, S.D.
United States
James
Reviewed October 23, 2026
Best Western Plus Lakeview Hotel

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

Frequently Asked Questions

Can I find vacation rentals in Chester?

Yes, you can find vacation rentals near popular local attractions in Chester, or you can go with a secluded option if you're looking for relaxation.

What can I see and do in Chester?

While you're exploring the area, Lake Madison and Lake Herman State Park are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Grand Opera House of Dell Rapids and Dakota State University.

What are vacation rentals like in Chester?

Vacation rentals are private accommodations you can book for several days or longer in Chester. Vacation rentals feature extras such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips.