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Annapolis Area Waterside Retreat

This Rhode River home is your perfect getaway to the Annapolis area - whether you’re looking to get away to a unique home overlooking incredible sunsets, a fun weekend with friends along the water, a family trip to the Chesapeake, or a private work retreat away from the bustle of the city, this home has it all. The house is a short drive from DC or Baltimore and unlike any Airbnb this side of the Chesapeake - it is on a 3 acre marina just minutes from Annapolis but private and away from it all!

1 bdrm Lux Suite & Retreat Minutes from Wineries

Kick back and relax in this calm, stylish space. This is a 1 bdrm Loft Style Private Basement with a bathroom, wetbar, and entrance. This location is on an exclusive 5-acre retreat that's tucked way & surrounded by beautiful nature. There is a lovely outdoor area, including waterfall, pond, firepit, and seating areas around the property. Enjoy a quick getaway/retreat or even a quiet work from home space only minutes from over 4 local wineries, Patuxent River, & 30 min from DC/ National Harbor.

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silver Water is a serene 5-star retreat for those who value tranquility over spectacle. Nestled along the Chesapeake, it offers front-row seats to mesmerizing sunsets, where golden light shimmers across the water. Inside, Nordic-inspired design pairs with quiet luxury, featuring award-winning mattresses and sumptuous bedding for deeply restorative sleep. Here, time slows, and luxury isn’t just seen—it’s felt. Discover why so many guests long to return by reading our reviews.

Bell Estates I Beautiful Cottage I *Beach Passes*

Bell Estates is a newly built corner lot across the street from the bay with minimal views of the water from Master bedroom and front yard. Located in the heart of North Beach in the exclusive Holland Point neighborhood, our home provides a cozy get-a-way for a family looking to escape the hustle and bustle of life. Home is 2 minutes away from Herrington Harbor, Ketch 22, North Beach Boardwalk & more. Enjoy local accessibility to fishing from the boardwalk dock or rent a boat to go crabbing.

In Huntingtown, Maryland - Close to the Beach

Private 1 bedroom apartment w/1 queen bed and a private entrance on a working animal sanctuary including a bathroom, eat in kitchen, work space, living room with 3 sofas & private washer/dryer. Surrounded by trees in Calvert County, your stay will be peaceful. You can interact with the critters or observe from afar. We currently have; geese, ducks, chickens, turkeys, a pig, parrots, emus, cats. Please note, if you have any mobility issues this may not be a good choice for your stay.

Chesapeake Bay Apartment w/Free Season Beach Pass!

Brookeside is an apartment above a garage, private from the main house. There is one bedroom, bathroom, and large living room with a pullout couch and cot. Most of the back property is environmentally protected Chesapeake Bay where you will enjoy birds singing all day. We are located just a few miles from a casino, waterpark, and beaches. From here it is very easy to explore everything on the western shore from Southern Maryland, DC, Baltimore, and historic Annapolis.

Hannah’s Hideaway

Cottage style with water view of Rockhold Creek. Water taxi right out front of house to take you to local restaurants. Crabbing excursions or fishing charters available for extra cost. Dog friendly. Local restaurants all within 1 mile from location. Fenced in back yard. Picnic table and fire pit to have own personal crab feasts or cookout. Many local restaurants with outside musicians.Grocery store and gas/liquor stores within 5 minutes from house.

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Savor our three-bedroom Cottage in this peaceful western shore spot, enjoy two acres of green space, the pier, kayaks, swings, fire pit, shady lawns & sun-drenched loungers, local waterfront dining or eat in, close to Washington, D.C., Annapolis, & Baltimore at this honeymoon-worthy country-like micro-resort. Due to the current COVID-19 situation, we have offered SPECIAL discounts for longer-term rentals

Chesapeake Bay Cottage

Cottage Located directly on the Chesapeake Bay. Includes sandy beach, yard, a screened in porch and deck. Two Kayaks to enjoy. Two bedroom plus den. Two full baths. Fully equipped kitchen.Kurig coffee maker and regular available. Master bedroom -queen size mattress. Second bedroom -a full-size mattress (double) third bedroom -a twin day bed with twin pullout. Both twin size mattresses.