Compare Chester Guest House Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Guest Houses in Chester

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Island Life! Kent Island Waterfront with Pool-Bring your boat!

Stevensville MD
Guests of this guesthouse enjoy features like an outdoor pool, a hot tub, and laundry facilities. Additional amenities include local meal delivery service, a garden, and barbecue grills.
Pool
Hot Tub
Riverview Retreat on Warehouse Creek - sleeps 6

Riverview Retreat on Warehouse Creek - sleeps 6

Edgewater MD
At this guesthouse, guests have access to features like laundry facilities.
Pet friendly
Air conditioning
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis

West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis

Annapolis MD
Guests staying at this guesthouse have access to laundry facilities, barbecue grills, and a garden.
Free WiFi
Air conditioning
Newly Renovated Guest House located in Oxford MD

Newly Renovated Guest House located in Oxford MD

Oxford MD
At this guesthouse, guests have access to a garden.
Free WiFi
Air conditioning
The Shallow Creek Shore Shack on the Chesapeake Bay

The Shallow Creek Shore Shack on the Chesapeake Bay

Sparrows Point MD
Guests staying at this guesthouse have access to a garden and barbecue grills.
Free WiFi
Air conditioning
Don't see what you're looking for?
See all available properties in Chester
View all properties
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.

Hotel Options in Chester

    DoubleTree by Hilton Hotel Annapolis

    DoubleTree by Hilton Hotel Annapolis

    210 Holiday Court Annapolis MD
    $83 nightly
    The price is $94 total per night from Jan 11 to Jan 12
    $94 total
    Jan 11 - Jan 12
    Total with taxes and fees
    8.6/10 Excellent! (1,003 reviews)
    Graduate by Hilton Annapolis

    Graduate by Hilton Annapolis

    126 West St Annapolis MD
    $147 nightly
    The price is $167 total per night from Jan 11 to Jan 12
    $167 total
    Jan 11 - Jan 12
    Total with taxes and fees
    9.2/10 Wonderful! (1,003 reviews)
    Historic Inns of Annapolis

    Historic Inns of Annapolis

    58 State Circle Annapolis MD
    $169 nightly
    The price is $193 total per night from Jan 6 to Jan 7
    $193 total
    Jan 6 - Jan 7
    Total with taxes and fees
    8.8/10 Excellent! (1,908 reviews)

Chester Guest Houses essential information

Accommodation
5 Guest Houses
Lowest Price
$94
Highest Price
$193
Popular accommodation
Island Life! Kent Island Waterfront with Pool-Bring your boat!, Riverview Retreat on Warehouse Creek - sleeps 6, West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis , Newly Renovated Guest House located in Oxford MD, The Shallow Creek Shore Shack on the Chesapeake Bay

More to Explore