Compare Chester Guest House Rentals

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Featured Guest Houses in Chester

Sandaway Suites & Beach

Sandaway Suites & Beach

3 out of 5
103 West Strand Road, Oxford, MD
Free Cancellation
Reserve now, pay when you stay
$280 nightly
The price is $308 total per night
$308 total
Oct 6 - Oct 7
Total with taxes and fees
Guests of Sandaway Suites & Beach enjoy features like a private beach, free WiFi in public areas, and a meeting room. If you drive, take advantage of free parking. Front-desk staff can assist with concierge services and securing valuables. Other amenities at this adults-only guesthouse include express check-in, express check-out, and a terrace.
On private beach
Parking included
Island Life! Kent Island Waterfront with Pool-Bring your boat!

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

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

$371 nightly
The price is $399 total per night
$399 total
Oct 21 - Oct 22
Total with taxes and fees
At this guesthouse, guests have access to features like laundry facilities.
Pet friendly
Air conditioning
Newly Renovated Guest House located in Oxford MD

Newly Renovated Guest House located in Oxford MD

At this guesthouse, guests have access to a garden.
Free WiFi
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

$385 nightly
The price is $438 total per night
$438 total
Oct 5 - Oct 6
Total with taxes and fees
Guests staying at this guesthouse have access to laundry facilities, barbecue grills, and a garden.
Free WiFi
Air conditioning
Calico Cottage Guest House

Calico Cottage Guest House

At this guesthouse, guests have access to features like laundry facilities. This smoke-free guesthouse also has a garden.
Air conditioning
Parking available
The Shallow Creek Shore Shack on the Chesapeake Bay

The Shallow Creek Shore Shack on the Chesapeake Bay

Guests staying at this guesthouse have access to barbecue grills and a garden.
Free WiFi
Air conditioning
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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

    Historic Inns of Annapolis

    Historic Inns of Annapolis

    58 State Circle, Annapolis, MD
    $145 nightly
    The price is $166 total per night from Nov 2 to Nov 3
    $166 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.8/10 Excellent! (1,833 reviews)
    Sonesta ES Suites Annapolis

    Sonesta ES Suites Annapolis

    170 Admiral Cochrane Dr, Edgewater, MD
    $113 nightly
    The price is $129 total per night from Oct 19 to Oct 20
    $129 total
    Oct 19 - Oct 20
    Total with taxes and fees
    8.8/10 Excellent! (906 reviews)
    Country Inn & Suites by Radisson, Annapolis, MD

    Country Inn & Suites by Radisson, Annapolis, MD

    2600 Housley Road, Annapolis, MD
    $97 nightly
    The price is $110 total per night from Nov 2 to Nov 3
    $110 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.8/10 Excellent! (1,004 reviews)

Chester Guest Houses essential information

Accommodation
7 Guest Houses
Lowest Price
$110
Highest Price
$438
Popular accommodation
Sandaway Suites & Beach, Island Life! Kent Island Waterfront with Pool-Bring your boat!, Riverview Retreat on Warehouse Creek - sleeps 6, Newly Renovated Guest House located in Oxford MD, West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis , Calico Cottage Guest House, The Shallow Creek Shore Shack on the Chesapeake Bay

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