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Vacation rentals in Shady Side

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Top-rated vacation rentals in Shady Side

Guests agree: these stays are highly rated for location, cleanliness, and more.

Cozy waterfront getaway on the Bay
SUPERHOST
Entire bungalow · 4 guests · 2 beds · 1 bath
Cozy waterfront getaway on the BayThis 2 BR waterfront home has a large, modern kitchen, comfy living rm and den, woodburning fp and hot tub. Hi speed FIOS & WiFi. Large pier & deck with stunning waterfront and sunset views. Enjoy birdwatching, kayaking, or soak in the hot tub!
Rockhold Creek Cottage
SUPERHOST
Entire cottage · 6 guests · 5 beds · 1.5 baths
Rockhold Creek CottageThe Perfect rock fishing and crabbing cottage in Deale, Maryland right on Rockhold Creek, with docks and spectacular views! The waterfowl are mesmerizing to watch. Just 1/2 block from Happy Harbor and Fishing Charters! No need to make that drive at 4am, you can stay the night before and after for maximum enjoyment!
Chesapeake Bay Cottage
SUPERHOST
Entire cottage · 8 guests · 4 beds · 2 baths
Chesapeake Bay CottageCottage Located directly on the Chesapeake Bay. Includes private little pier, sandy beach, yard, a screened in porch and deck. Two Kayaks to enjoy. Three bedroom. Two full baths. Fully equipped kitchen.Kurig coffee maker and regular available. Master bedroom -queen size. Second bedroom -a full-size (double) third bedroom -a twin day bed with twin pullout. Full size air mattress available.

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Popular amenities for Shady Side vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Shady Side

SUPERHOST
  1. Entire rental unit
  2. Deale
Romantic Chesapeake Waterfront Flat!
SUPERHOST
  1. Entire residential home
  2. Deale
PET-FRIENDLY WATERFRONT FALL OASIS WITH FIRE-PIT
SUPERHOST
  1. Entire residential home
  2. Shady Side
Waterfront w/ Private Pier, 35 Mins to Annapolis
SUPERHOST
  1. Entire cottage
  2. Deale
Wonderful Waterfront Bungalow-Kayaks/Dogs OK/Nr DC
SUPERHOST
  1. Entire residential home
  2. Shady Side
Cattail Landing- Photographer's Waterfront Retreat
  1. Entire residential home
  2. Deale
Hannah’s Hideaway
SUPERHOST
  1. Entire residential home
  2. Deale
Chesapeake Waterfront/DC 33 Miles/Spa-Kayaks-SUP
  1. Entire cottage
  2. West River
Waterfront Cottage with Beach and Dock
  1. Entire guesthouse
  2. Galesville
Gorgeous water view studio!
  1. Entire residential home
  2. Shady Side
"PIER JOY!" - 3BR WATERFRONT HOME W/PRIVATE DOCK
  1. Entire residential home
  2. Shady Side
Luxe Waterfront Private Getaway on Chesapeake Bay!
SUPERHOST
  1. Entire residential home
  2. Deale
Gorgeous Views Waterfront Home/Huge Screened Porch