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Maryland Holiday Rentals

Featured Destinations in Maryland
Ocean City
McHenry
Oakland
Swanton
Annapolis
Baltimore
Berlin
Cambridge
The 10 Best Holiday Rentals in Maryland
Waterfront House, pier, close to Betterton Chestertown & Rockhall
Magothy River rustic retreat home.
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Gorgeous Colonial House with an Oasis Backyard
Magnolia Point, Charming 3 Bedroom 2 Bath Cottage
Waterfront Family Retreat with Pool on 7+ acres!
Potomac Vista Cottage on Little Pond
Renovated Waterfront Beach House; Private Beach
7acre Island Estate with 600 foot Private Beach & Pier. Ranked #1 by VRBO!
Barbara's Villa on the Pocomoke River - A Splendid Riverfront Single Family Home
Family Friendly Holiday Rentals in Maryland
waterfront beach retreat with boat dock
Vintage Eastern Shore Retreat
D and D Farm - Quiet Getaway
Play & relax at the Bungalow! Easily walk to beautiful Herrington Harbour South!
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*
WATERFRONT - DRIFTWOOD LODGE
Professionally Cleaned -Waterfront Retreat with Pool Located on Taylors Island
Modern Beach House with Amazing panoramic VIEWS, multi level decks and firepit!!
Blissful Retreat In Rock Hall
Life is better at the RIVER!--Cozy waterfront cottage
Pet Friendly Holiday Rentals in Maryland
Potomac River Retreat | Shepherdstown, WV | Stunning views | 5 acres | 4 BR
Private Waterfront Home w/ Pier and 2+ Acres!
The Perfect Relaxing, Fun, Dog-Friendly Get-Away for Families, Groups or Couples
Newly Renovated Home With Impressive Views Of The 7Th Green!
BAYVIEW HOME, GETAWAY, RELAX, EAT FRESH CRABS n FISH, PEACEFUL, SCENIC, MEMORABL
Entire Extra Large Luxury 3 bedroom Condo
BEAUTIFUL BAY FRONT VIEW
A Vacation Away From It All-Family And Pet Friendly
Cozy cabin-style home w/ private hot tub and entertainment - dogs welcome!
Summerlee - Luxury Chesapeake Bay Waterfront with Sandy Beach!
The Top 10 Rated Holiday Rentals in Maryland
Eastern Shore Get Away
Chesapeake Bay House on Private Beach
This house is a 6 bedroom(s), 6 bathrooms, located in Earleville, MD.
Newly custom built cottage w/ modern amenities, quietly nestled among the Osprey
Potomac River Getaway at McKays Beach
Pet-friendly waterfront home close to St.Mary's College
Victorian on Main Street, Rock Hall MD. Walk to everything! Sleeps 2-4
Beach cottage with a spectacular view!
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Hom
A waterfront vacation rental located on the Chesapeake Bay

All Maryland Holiday Rentals

Montgomery County
Talbot County
Calvert County
Garrett County