Compare Chester Guest House Rentals

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Featured Guest Houses in Chester

The Tilghman Island Inn

The Tilghman Island Inn

3.5 out of 5
21384 Coopertown Rd Tilghman MD
Free Cancellation
Reserve now, pay when you stay
$225 nightly
The price is $248 total per night
$248 total
Aug 9 - Aug 10
Total with taxes and fees
The Tilghman Island Inn features free WiFi in public areas, a seasonal outdoor pool, and microwave in a common area. A stay here includes free parking. Multilingual staff is on hand to answer questions. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Additional amenities include a refrigerator in a common area, a terrace, and wedding services.
Pool
Breakfast included
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
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
$328 nightly
The price is $374 total per night
$374 total
Jul 12 - Jul 13
Total with taxes and fees
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
Stay Barefoot•Bikes•Kayaks•Bay Access•USNA

Stay Barefoot•Bikes•Kayaks•Bay Access•USNA

annapolis MD
Guests staying at this guesthouse have access to laundry facilities, a garden, and barbecue grills.
Pet friendly
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
    $130 nightly
    The price is $148 total per night from Jul 19 to Jul 20
    $148 total
    Jul 19 - Jul 20
    Total with taxes and fees
    9/10 Wonderful! (1,893 reviews)
    DoubleTree by Hilton Hotel Annapolis

    DoubleTree by Hilton Hotel Annapolis

    210 Holiday Court Annapolis MD
    $103 nightly
    The price is $118 total per night from Jul 12 to Jul 13
    $118 total
    Jul 12 - Jul 13
    Total with taxes and fees
    8.6/10 Excellent! (1,030 reviews)
    Crowne Plaza Annapolis by IHG

    Crowne Plaza Annapolis by IHG

    173 Jennifer Rd Annapolis MD
    $118 nightly
    The price is $134 total per night from Jul 15 to Jul 16
    $134 total
    Jul 15 - Jul 16
    Total with taxes and fees
    8.8/10 Excellent! (1,011 reviews)

Chester Guest Houses essential information

Accommodation
3 Guest Houses
Lowest Price
$118
Highest Price
$374
Popular accommodation
The Tilghman Island Inn, Island Life! Kent Island Waterfront with Pool-Bring your boat!, West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis , Newly Renovated Guest House located in Oxford MD, Stay Barefoot•Bikes•Kayaks•Bay Access•USNA

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