1. USA
  2. Indiana
  3. Chesterfield
  4. Cottage Rentals

Chesterfield Cottage Rentals & Holiday Homes

Find the best cottages in Chesterfield - We found 44 exact matches

About Chesterfield Luxury Rental on Luxury Cruises

Searching for cottages to rent near Chesterfield? Luxury Cruises features more than 44 cottages that are perfect for your next trip. Discover luxury cottage rentals that are a few miles away from the lake or beach. These cottage rentals in Chesterfield have hot baths, are kid-friendly & family-friendly, and are near top local attraction spots, to give guests the best travel experience they could ever wish for. Luxury Cruises’s cottage listings come in all shapes and sizes for large groups, friends, or couples in Chesterfield.

Are you planning to travel to the lakeside, beach, or mountain area? Luxury Cruises’s cottage rentals offers a wide selection, giving you direct access to the owners of these cottage rentals, and offering you the best opportunity to find a good price.

Luxury Cruises boasts of 44 holiday cottages and places to stay in Chesterfield. The site provides unique Airbnb, VRBO, Luxury Cruises-style cottages to fit your trip or get away with your friends and family. This can be a weekend getaway, spring break, summer vacation, or annual holiday -- all fitting within your budget.

Frequently Asked Questions About Chesterfield Cottage Rentals

What are the top rated Cottage Rentals in Chesterfield?

There are a lot of options in Chesterfield. If you plan on staying in the Chesterfield area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Chesterfield:

How much does it cost to rent a cottage in Chesterfield?

The average cost for a cottage rental in Chesterfield is $123 per night. Luxurycruises has a wide list of great cottages near Chesterfield that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Do you have any rental cottages in Chesterfield that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Chesterfield to find one that works for you.

Are there quality cottages in Chesterfield that have indoor swimming pools?

As of 2026, the data from Luxurycruises shows that there are Over 44 private swimming pools or cottages with indoor pools in the Chesterfield area along with other great amenities.