
Waterfront holiday rentals in St. Mary's County
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Top-rated waterfront rentals in St. Mary's County
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for waterfront rentals in St. Mary's County
Waterfront apartment rentals

Heron's Rest

The Solomons Sunrise Suite

Waterfront Views + King Bed | Solomons Island

Furnished Corporate Apartment Near NAS Pax

Blue Heron on Little Kingston Creek

Serenity Suite on Chesapeake Bay
Waterfront house rentals

Osprey's roost: Spring and summer 2025

Waterfront Studio | Bikes & Kayaks | Beach Access

Million dollar view on the Chesapeake Bay w/dock!

Waterfront Home: Osprey Getaway

Coastal Oasis On The Chesapeake, King Bd sleeps 12

New Private Beachfront panoramic view every window

The Glebe

Stunning Views, Remodeled Family-Friendly Home
Other waterfront holiday rentals

Block to Private Beach, Screened deck, Hot Tub

Charming Waterfront Cottage with Sunset Views

Pizza Friday

The Little Blue Cottage

Waterfront Paradise

Island Shanty

Waterfront New Piney Point A-Frame

4-BR Unique Waterfront House - Your Perfect Escape
Destinations to explore
- Rentals with pools St. Mary's County
- Rentals with a firepit St. Mary's County
- Rentals with outdoor seating St. Mary's County
- Rentals with a hot tub St. Mary's County
- Rentals with a fireplace St. Mary's County
- Flat rentals St. Mary's County
- Beachfront rentals St. Mary's County
- Rentals with lake access St. Mary's County
- Rentals with a kayak St. Mary's County
- Pet-friendly rentals St. Mary's County
- Rentals with a washing machine and dryer St. Mary's County
- Cottage rentals St. Mary's County
- Rentals with breakfast St. Mary's County
- Rentals with a patio St. Mary's County
- Rentals with beach access St. Mary's County
- House rentals St. Mary's County
- Waterfront rentals Maryland
- Waterfront rentals United States
- Chesapeake Bay
- Haven Beach
- Bethel Beach
- Breezy Point Beach & Campground
- Piney Point Beach
- Ragged Point Beach
- Chesapeake Beach Water Park
- Rose Haven Memorial Park
- Sandyland Beach
- Gerry Boyle Park
- St George Island Beach
- Saint Jerome Beach
- Franklin Manor Community Private Park
- North Beach Boardwalk/Beach
- Bayfront Beach
- Guard Shore
- Marshalls Beach
- Brownies Beach
- Cordreys Beach
- Oxford Beach
- Langford Sand
- Lane Beach
- Cove Point Beach
- General's Ridge Vineyard