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

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

  • Check prices for these dates

    Check prices for these dates, December 14 – 15, 2026

    View in a map

    Our top choices for Chester guest houses

    1. The DeBary Inn

    A covered porch with wicker furniture, a dining table, and a view of a red house across the fence.

    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.

    Frequently Asked Questions

    What is the nightly rate for a guest house in Chester?

    Rates for Chester guest houses vary, but travelers can find great-value prices from $172 with Expedia. A range of factors can affect nightly rates, such as the location, the breakfast offering, and the range of amenities. Travelers looking for a good deal should consider looking for a midweek stay, as weekend rates at Chester guest houses tend to be higher. Remember to also use our filters to sort prices from low to high.

    What's the difference between a Chester guest house and a B&B?

    A guest house in Chester is typically a larger establishment with more rooms, offering a more hotel-like experience, and may provide additional amenities including luxury bedding. In contrast, a B&B is usually a smaller property that focuses primarily on providing a room and breakfast. A B&B is often more personal, and breakfast is typically included as part of the stay, but other services might be more limited compared to a guest house.

    Explore a world of travel with Expedia