Shady Side Holiday Rentals
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46 rentals in Shady Side.
Waterfront Home on the Chesapeake Bay!
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The Cottage
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5-years young STUNNING home with water view!
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Bay views with kayaks, bikes, fire pit, crabbing and more
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Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
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Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi
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Private Waterview Estate with 4 bedroom Suites, game room and Hot Tub
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Calloway Drive Retreat | House in Shady Side
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Pier Relaxation! * the Chesapeake Bay!
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Water views from every window of unique round house
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"PIER JOY!" - 3BR WATERFRONT HOME W/PRIVATE DOCK
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The following properties within 20 miles of Shady Side match all your filters:
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
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Waterfront Cheerful 6 BR Home with Private Pier
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Private waterfront mansion w/ 7 bedrooms near Annapolis
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Pristine Waterfront Home with Expansive Views.
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Chesapeake Bay Cottage
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Spacious Luxury 6 BR Home, Sleeps 15, Private Pool, In Nature, Convenient to DC
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Sunrise Suite Exquisite Bay View Lux/Rom/Spiritual
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Waterfront Getaway, Dock Your Boat & Play!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Chesapeake Bay Getaway | New Waterfront With Private Pier | Near Annapolis
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Adorable waterside cottage with pool Beach community
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Coastal Edgewater Home w/ Private Hot Tub!
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Edgewater/Mayo Getaway!
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A quiet, family retreat home on the Chesapeake Bay, south of Annapolis MD
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Modern Bay Dream
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Water Views- Boating Fishing -Annapolis-DC-Chesapeake Bay-Kayaking-Paddle Boards
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Carriage House on 42 Acres in West River. Just 17 Miles from Annapolis.
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This house is a 3 bedroom(s), 2 bathrooms, located in Edgewater , MD.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Chesapeake Sparkles Sky-Lit Studio Flat + Solarium
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New Waterfront Home near Annapolis, MD
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Chesapeake Bayside Loft
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Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
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Chesapeake Paradise House-Stunning 6+br4ba Wtrfrnt
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Searenity Stays, a Cozy Home
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Watrfnt Cottage *ChesapeakeParadise Kayaks/Dogs OK
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Rockhold Creek Cottage, Water Front, Vacation Home, Docks
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Enchanting West River Retreat
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Nautical Charm with Relaxing Waterviews! Your Chesapeake Getaway!
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Riverside Retreat - Views Galore. Near DC/Baltimore and Annapolis, MD
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Chesapeake Paradise LITE 4-5 Br 3 Ba Vacation Home
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Special Rates. Close to Annapolis. Justin Beach Cottage Retreat
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Private Waterfront Home w/ Pier and 2+ Acres!
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Grandma's Summer House * Beverly Beach
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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42 Acres of Serenity & Nature Just15 Miles To Annapolis
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Spacious 5-bedroom house with Pier, AC and WiFi in delightful Edgewater
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Chesapeake Spectacular Waterfront- Kayaks, Spa, Pier
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Showing results 1-46 of 46
Frequently Asked Questions about Shady Side
- Yes, here are some popular holiday rentals in Shady Side that have a pool:See all holiday rentals with a pool in Shady Side on Tripadvisor
- Yes, here are some popular holiday rentals in Shady Side that have internet access:See all holiday rentals in Shady Side on Tripadvisor
- The best pet friendly rentals in Shady Side are:See all pet friendly holiday rentals in Shady Side on Tripadvisor
- Some of the most popular kid friendly rentals in Shady Side are:See all kid friendly holiday rentals in Shady Side on Tripadvisor
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