Shady Side Vacation Rentals
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5 mi
45 rentals in Shady Side.
Bay views with kayaks, bikes, fire pit, crabbing and more
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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"PIER JOY!" - 3BR WATERFRONT HOME W/PRIVATE DOCK
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
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Private Waterview Gladstone Manor with 4 Master Suites
Rental Home
6 bedrooms
5 bathrooms
Sleeps 14
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Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
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Waterfront Home on the Chesapeake Bay!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Calloway Drive Retreat | House in Shady Side
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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5-years young STUNNING home with water view!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
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Pier Relaxation! * the Chesapeake Bay!
Rental Home
6 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The following properties within 20 miles of Shady Side match all your filters:
Serene house, sweet neighborhood, West River dock, 5 1/2 MLW, sunset view.
Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Carriage House on 49 Acres in West River. Just 17 Miles from Annapolis.
Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Million Dollar View of the Chesapeake Bay
Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Rental Home
3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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Waterfront Cheerful 6 BR Home with Private Pier
Rental Home
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Chesapeake Bayside Loft
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Private Waterfront Home w/ Pier and 2+ Acres!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Waterfront w/ Pool Minutes To Annapolis
Rental Home
7 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Quaint cottage with serene water view!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Pristine Waterfront Home with Expansive Views.
Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Chesapeake Bay Cottage
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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New! Amazing Chesapeake Paradise Wtrfrnt Home 6-7 Brm 4 Ba w/Scr Porch/Kayaks
Rental Home
8 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Spacious Luxury 6 BR Home, Sleeps 15, Private Pool, In Nature, Convenient to DC
Rental Home
6 bedrooms
6 bathrooms
Sleeps 15
Match: Sleeps
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Waterfront Getaway, Dock Your Boat & Play!
Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Special Rates. Close to Annapolis. Justin Beach Cottage Retreat
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Chesapeake Bay Getaway | New Waterfront With Private Pier | Near Annapolis /USNA
Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Adorable waterside cottage with pool Beach community
Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Romantic Wtrfrnt Flat+Solarium*Chesapeake Paradise
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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*Chesapeake Bayside Bungalow*
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Searenity Stays, a Cozy Home
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gourmet Kitchen + Family & Pet Friendly Residence!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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Showing results 1-30 of 45
Frequently Asked Questions about Shady Side
- Yes, here are some popular vacation rentals in Shady Side that have a pool:
- Bay views with kayaks, bikes, fire pit, crabbing and more
- "PIER JOY!" - 3BR WATERFRONT HOME W/PRIVATE DOCK
- Private Waterview Gladstone Manor with 4 Master Suites
- Yes, here are some popular vacation rentals in Shady Side that have internet access:
- Bay views with kayaks, bikes, fire pit, crabbing and more
- "PIER JOY!" - 3BR WATERFRONT HOME W/PRIVATE DOCK
- Private Waterview Gladstone Manor with 4 Master Suites
- Some of the most popular kid friendly rentals in Shady Side are:
- Bay views with kayaks, bikes, fire pit, crabbing and more
- "PIER JOY!" - 3BR WATERFRONT HOME W/PRIVATE DOCK
- Private Waterview Gladstone Manor with 4 Master Suites
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