West Chesterfield Cottage Rentals & Holiday Homes

Find the best cottages in West Chesterfield - We found 26 exact matches

About West Chesterfield Cottage Rentals on PickleTrip

Searching for cottages to rent near West Chesterfield? PickleTrip™ features more than 26 cottages that are perfect for your next pickleball getaway. Plan your ultimate holiday and discover luxury cottage rentals that are a few miles away from the lake or beach and have access to private courts or nearby facilities. These cottage rentals in West 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. PickleTrip™’s cottage listings come in all shapes and sizes for large groups, friends, or couples in West Chesterfield.

Are you planning to travel to the lakeside, beach, or mountain area? PickleTrip™’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.

PickleTrip™ boasts of 26 holiday cottages and places to stay in West Chesterfield. The site provides unique Airbnb, VRBO, pickleball-ready 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.

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Frequently Asked Questions About West Chesterfield Rental Cottages

There are a lot of options in West Chesterfield. If you plan on staying in the West 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 West Chesterfield:

The average cost for a cottage rental in West Chesterfield is $161 per night. PickleTrip has a wide list of great cottages near West Chesterfield that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Yes, here are the top cottage rentals in West Chesterfield that allow you to bring your pet:

See all pet-friendly vacation rentals in West Chesterfield on PickleTrip

Most of our listed cottages are suitable for families. Check out the complete list of cottages in West Chesterfield to find one that works for you.
As of 2025, the data from PickleTrip shows that there are Over 26 private swimming pools or cottages with indoor pools in the West Chesterfield area along with other great amenities.
About 26 cottages in West Chesterfield boast of premium hot tubs. Some of the popular places to stay with hot tubs include:See all holiday vacation rentals in West Chesterfield on PickleTrip
Yes, there are luxury cottages in West Chesterfield. Find more luxury, lakefront, winter, & last-minute cottage rentals near West Chesterfield.