35 stays

Stays in Shady Side

Entire residential home in Shady Side
Luxe Waterfront Private Getaway on Chesapeake Bay!
11 guests5 bedrooms6 beds2 baths
Air conditioningFree parkingWifiKitchen
$311 per night
SUPERHOST
Entire residential home in Shady Side
Cattail Landing- Photographer's Waterfront Retreat
8 guests4 bedrooms5 beds3.5 baths
Air conditioningFree parkingWifiKitchen
$311 per night
Entire residential home in Shady Side
"Pier Envy!" Beach access & water-view-West River
8 guests4 bedrooms5 beds3 baths
Air conditioningFree parkingWifiKitchen
$400 per night
Entire residential home in Shady Side
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
6 guests3 bedrooms3 beds2 baths
Air conditioningFree parkingWifiKitchen
$351 per night
SUPERHOST
Entire residential home in Shady Side
Waterfront w/ Private Pier, 35 Mins to Annapolis
8 guests4 bedrooms8 beds2.5 baths
Air conditioningFree parkingWifiKitchen
$425 per night
SUPERHOST
Entire residential home in Shady Side
Chesapeake Bay waterfront home - easy getaway
6 guests3 bedrooms5 beds2.5 baths
Air conditioningFree parkingWifiKitchen
$191 per night
Entire guesthouse in Galesville
Gorgeous water view studio!
3 guestsStudio2 beds1 bath
Air conditioningFree parkingWifiKitchen
$165 per night
SUPERHOST
Entire residential home in Shady Side
Riverfront tranquility less than one hour from DC.
7 guests3 bedrooms4 beds2 baths
Air conditioningFree parkingWifiKitchen
$1,040 per night
SUPERHOST
Entire bungalow in Deale
Cozy waterfront getaway on the Bay
4 guests2 bedrooms2 beds1 bath
Air conditioningFree parkingWifiKitchen
$174 per night
SUPERHOST
Entire residential home in Deale
*Sunrise @ Chesapeake*
6 guests3 bedrooms3 beds2 baths
Air conditioningFree parkingWifiKitchen
$299 per night
SUPERHOST
Entire cottage in Deale
Rockhold Creek Cottage
6 guests3 bedrooms5 beds1.5 baths
Air conditioningFree parkingWifiKitchen
$214 per night
SUPERHOST
Entire cottage in Deale
Chesapeake Bay Cottage
8 guests3 bedrooms4 beds2 baths
Air conditioningFree parkingWifiKitchen
$290 per night
SUPERHOST
Entire rental unit in Deale
Romantic Chesapeake Waterfront Flat!
2 guests1 bedroom1 bed1 bath
Air conditioningFree parkingWifiKitchen
$162 per night
Entire cottage in West River
Waterfront Cottage with Beach and Dock
11 guests4 bedrooms9 beds3 baths
Air conditioningFree parkingWifiKitchen
$350 per night
SUPERHOST
Entire cottage in Deale
Wonderful Waterfront Bungalow-Kayaks/Dogs OK/Nr DC
8 guests3 bedrooms3 beds2 baths
Air conditioningFree parkingWifiKitchen
$278 per night
SUPERHOST
Entire residential home in Deale
Gorgeous Views Waterfront Home/Huge Screened Porch
5 guests2 bedrooms3 beds1 bath
Air conditioningFree parkingWifiKitchen
$229 per night
SUPERHOST
Private room in Edgewater
Beverly Beach House; Main Deck
2 guests1 bedroom1 bed1 private bath
Air conditioningFree parkingWifiKitchen
$140 per night
Entire residential home in Deale
8 ACRE PET-FRIENDLY FALL OASIS WITH FIRE-PIT
10 guests3 bedrooms4 beds2 baths
Air conditioningFree parkingWifiKitchen
$360 per night
Entire residential home in Deale
Hannah’s Hideaway
8 guests3 bedrooms7 beds2 baths
Air conditioningFree parkingWifiKitchen
$225 per night
SUPERHOST
Private room in Deale
Glamping in the Carriage House
3 guests1 bedroom1 bed0 baths
Air conditioningFree parking
$92 per night
1 – 20 of 35 places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.