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
$205 nightly
The price is $226 total per night
$226 total
Sep 16 - Sep 17
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.
Pool
Breakfast included

Island Life! Kent Island Waterfront with Pool-Bring your boat!
Stevensville MD
This guesthouse features an outdoor pool and a hot tub. A garden, laundry facilities, and barbecue grills are also on offer.
Pool
Hot Tub

West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
Annapolis MD
$300 nightly
The price is $342 total per night
$342 total
Sep 9 - Sep 10
Total with taxes and fees
This guesthouse features a garden, laundry facilities, and barbecue grills.
Free WiFi
Air conditioning
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

Lovely bay views with kayaks, bikes, fire pit, crabbing & more
Shady Side MD
9.6/10 Exceptional! (38 reviews)
Shady Side Guest Houses essential information
Accommodation | 5 Guest Houses |
|---|---|
Lowest Price | $95 |
Highest Price | $342 |
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, Barefoot Cottage A Quiet Coastal Retreat |
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