Shady Side Rentals
From $195 per night (USD)VRBO
Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still only a 30 minute drive to Annap ...
From $195 per night (USD)VRBO
From $237 per night (USD)VRBO
Chesapeake Sparkles Sky-Lit Studio Flat + Solarium
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Your party will have two lovely private spaces, connected by a door, on the second floor of the Chesapeake Paradise Hou ...
From $237 per night (USD)VRBO
From $114 per night (USD)VRBO
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
A perfect getaway spot, on a peninsula on the West River just across from Galesville. Houses on the point are mostly w ...
From $114 per night (USD)VRBO
From $933 per night (USD)Expedia
Private Waterview Estate with 4 Suites, Hot Tub, Gourmet Kitchen and Game Room
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Welcome to Sanare Estates! The ultra-private waterfront estate is like your own luxury resort, located on 20+ Acres with ...
From $933 per night (USD)Expedia
From $162 per night (USD)VRBO
Chesapeake Bayside Loft
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Recently updated 1 bedroom, 1 bathroom loft studio unit with fully equipped kitchen, Smart TV in bedroom and free high s ...
From $162 per night (USD)VRBO
From $418 per night (USD)VRBO
5-years young STUNNING home with water view!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
5-years-young STUNNING home with OPEN concept, soaring ceilings, hardwoods, gas fireplace, separate laundry room, backya ...
From $418 per night (USD)VRBO
From $340 per night (USD)VRBO
\"PIER JOY!\" - 3BR WATERFRONT HOME W/PRIVATE DOCK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gorgeous view, expansive covered back porch with fans & cascading stairs down to paver patio, fire pit and a dock where ...
From $340 per night (USD)VRBO
From $523 per night (USD)Expedia
Waterfront Home on the Chesapeake Bay!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Expansive views of the Cheasapeake Bay, located on the West River this home is private, peaceful and immaculate. Home in ...
From $523 per night (USD)Expedia
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Pier Relaxation! @ the Chesapeake Bay!
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 6
Pier Relaxation with the whole family at this peaceful place to stay on the Chesapeake Bay! Fishing or crabbing from th ...
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From $803 per night (USD)VRBO
A quiet, family retreat home on the Chesapeake Bay, south of Annapolis MD
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
A perfect spot for relaxing, reading, and writing, or as a home-base for visiting the many cultural and natural attracti ...
From $803 per night (USD)VRBO
From $320 per night (USD)VRBO
Bay views with kayaks, bikes, fire pit, crabbing and more
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Charming 3 bedroom, 2 bathroom private cottage is situated in a water community on the beautiful Chesapeake Bay. Take ...
From $320 per night (USD)VRBO
From $275 per night (USD)Expedia
Sunrise Suite Exquisite Bay View Lux/Rom/Spiritual
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Upscale luxury. relaxing romantic suite w/spectacular views. You won't want to leave your bed/bath! Brand new top floo ...
From $275 per night (USD)Expedia
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Riverside Retreat - Views Galore. Near DC/Baltimore and Annapolis, MD
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Let the Riverside Retreat be your next home away from home! This light and airy home is newly renovated with waterfront ...
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From $225 per night (USD)Expedia
Calloway Drive Retreat | House in Shady Side
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Calloway Drive Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $225 per night (USD)Expedia
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The Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
A beautifully furnished quiet oasis to kick back and relax or if you are fast paced, you can visit many of the attractio ...
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From $746 per night (USD)VRBO
Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 13
Welcome to our waterfront oasis on Parish’s Creek just off of the Chesapeake Bay! Our spacious house is the perfect retr ...
From $746 per night (USD)VRBO
From $674 per night (USD)VRBO
Waterfront Sanctuary only 50 Min. From DC/Balt.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
New listing on VRBO!! Please see other sites for 50+ reviews on this property. New full home renovation with gourmet ki ...
From $674 per night (USD)VRBO
From $475 per night (USD)VRBO
Enchanting West River Retreat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our charming waterfront cottage nestled on the serene shores of the West River! Perfectly positioned with a 3 ...
From $475 per night (USD)VRBO
From $829 per night (USD)VRBO
Zen Sunset Retreat on Waterfront at West River, MD
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
De-stress, Relax and Heal at our stunning, newly-constructed 3-story waterfront Zen Sunset Retreat (ZSR), with tons of a ...
From $829 per night (USD)VRBO
From $781 per night (USD)Expedia
Home w/ Beach Access Boat Slip Basketball Court
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
As the Sun rises and sets over the Bay, experience Shady Side with direct beach access, the Bayside BBQ Grill in your ba ...
From $781 per night (USD)Expedia
From $217 per night (USD)VRBO
Cozy and modern Bayfront home with.large kitchen, private pier and hispeed WiFi
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Deale is waiting for you at this modernized 2-bedroom bungalow. Nestled in a tranquil setting, this fantastic property o ...
From $217 per night (USD)VRBO