Shady Side Rentals
From $290 per night (USD)VRBO
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
A quiet, seaside escape awaits at this Shady Side vacation rental, hosting 3 bedrooms, 2 baths, at-home comforts and acc ...
From $290 per night (USD)VRBO
From $426 per night (USD)Expedia
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 $426 per night (USD)Expedia
From $965 per night (USD)VRBO
West River Waterscape - Where Nature's Whisper Beckons
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
STR00845 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $965 per night (USD)VRBO
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Dock of the Back Bay - 3 BR Waterfront Coastal Haven with Private Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
STR00899 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
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From $340 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 $340 per night (USD)VRBO
From $830 per night (USD)Expedia
Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Visit the magic of Annapolis during the Holiday Season Welcome to Sanare Estates! The ultra-private waterfront estate is ...
From $830 per night (USD)Expedia
From $430 per night (USD)VRBO
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 ...
From $430 per night (USD)VRBO
From $337 per night (USD)VRBO
\"PIER JOY!\" - 3BR WATERFRONT HOME W\/PRIVATE DOCK
- Bedrooms:
- 3
- 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 $337 per night (USD)VRBO
From $323 per night (USD)VRBO
Pier Relaxation! @ the Chesapeake Bay!
- Bedrooms:
- 2
- Bathrooms:
- 7
- Sleeps:
- 6
Pier Relaxation with the whole family at this peaceful place to stay on the Chesapeake Bay! Fishing or crabbing from th ...
From $323 per night (USD)VRBO
From $338 per night (USD)Expedia
Bay views with kayaks, bikes, fire pit, crabbing and more
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Updated 3 bedroom, 2 bathroom private cottage is situated in a water community on the beautiful Chesapeake Bay. Take a ...
From $338 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 $241 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 $241 per night (USD)Expedia
From $465 per night (USD)VRBO
Water views from every window of unique round house
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Visit the magic of Annapolis during the Holiday Season Tucked between the Chesapeake Bay and 500 acres of state park, th ...
From $465 per night (USD)VRBO
From $400 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 $400 per night (USD)Expedia
From $185 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 $185 per night (USD)VRBO
From $254 per night (USD)VRBO
*Chesapeake Bayside Bungalow*
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Amazing three bedroom two bath home only 20 miles from Annapolis! You will be a quick walk away from the Chesapeake Bay ...
From $254 per night (USD)VRBO
From $622 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 $622 per night (USD)VRBO
From $308 per night (USD)Expedia
Watrfnt Cottage @ChesapeakeParadise Kayaks\/Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Escape the city hustle to relax on the Chesapeake! Savor our three-bedroom Cottage in this peaceful western shore spot w ...
From $308 per night (USD)Expedia
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 $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 $793 per night (USD)VRBO
Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi
- Bedrooms:
- 4
- 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 $793 per night (USD)VRBO
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Chesapeake Bayside Bungalow
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Beautiful 3-bedroom, 2-bath home just 20 miles from Annapolis, nestled in the charming neighborhood, a short wa ...
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From $161 per night (USD)VRBO
Chesapeake Bayside Loft
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Charming 1-bedroom, 1-bathroom loft studio just a block from the bay, perfect for resting between adventures. L ...
From $161 per night (USD)VRBO
From $224 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 $224 per night (USD)VRBO
From $132 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 $132 per night (USD)VRBO
From $367 per night (USD)Expedia
Chesapeake Paradise LITE 4+br3ba Peaceful Watrfrnt
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
This is a fabulous 4-5 bedroom 3-ba House, affectionately called Porchlandia, with spectacular views on a lush, waterfro ...
From $367 per night (USD)Expedia
From $224 per night (USD)VRBO
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 $224 per night (USD)VRBO
From $711 per night (USD)Expedia
Chesapeake Paradise House-Stunning 6+br4ba Wtrfrnt
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 13
Chesapeake Paradise ("The Paradise") is a stunning, recently remodeled, luxurious, two-story 6+ bedroom 4 bath waterfron ...
From $711 per night (USD)Expedia