Plan your trip

A stone building with a blue roof, surrounded by a stone wall and wooden troughs for water collection.

Search Guest Houses in Chester from CA $217

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Sign in

  • Be picky

    Search almost a million properties worldwide

  • Check prices for these dates

    Check prices for these dates, December 12–13, 2026

    View in a map

    Our top choices for Chester guest houses

    1. The DeBary Inn

    A covered porch with a wooden floor, a wicker chair with cushions, and a lantern.

    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.

    View all properties

    Learn more about Chester

    Wander through charming streets lined with unique shops and eateries in this quaint borough. Pick your own fresh produce at Alstede Farms or explore the historic Cooper Gristmill for a taste of local heritage.

    See all hotels in Chester

    A stone building with a blue roof, surrounded by a stone wall and wooden troughs for water collection.

    Explore a world of travel with Expedia