Book Guest Houses in Shady Side, MD

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Top Guest Houses in Shady Side

The Tilghman Island Inn

21384 Coopertown Rd Tilghman MD

Free Cancellation

Reserve now, pay when you stay

$225 nightly

$248 total

Aug 9 - Aug 10

Total with taxes and fees

This guesthouse doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. Enjoy the seasonal outdoor pool and conveniences like a terrace and wedding services.

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

Stevensville MD

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This guesthouse features an outdoor pool and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.

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

Annapolis MD

$335 nightly

$382 total

Jul 20 - Jul 21

Total with taxes and fees

This guesthouse features a garden, laundry facilities, and barbecue grills.

Deluxe Basement Guest Suite w/ Luxury Amenities Minutes From BWI/Annapolis/DC

Odenton MD

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This guesthouse features free WiFi in public areas, a garden, and laundry facilities. Barbecue grills are provided for your convenience.

Stay Barefoot•Bikes•Kayaks•Bay Access•USNA

annapolis MD

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This guesthouse features a garden, laundry facilities, and barbecue grills.

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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.

Top hotels in Shady Side

Historic Inns of Annapolis

58 State Circle Annapolis MD

$136 nightly

$155 total

Aug 16 - Aug 17

Total with taxes and fees

9/10 Wonderful! (1,885 reviews)

Shady Side Guest Houses essential information

Accommodation	5 Guest Houses
Lowest Price	$105
Highest Price	$382
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 , Deluxe Basement Guest Suite w/ Luxury Amenities Minutes From BWI/Annapolis/DC, Stay Barefoot•Bikes•Kayaks•Bay Access•USNA