Beachfront vacation rentals in Queen Anne's County

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Top-rated beachfront rentals in Queen Anne's County

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Top guest favorite
A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.
Home in Grasonville
4.95 out of 5 average rating, 284 reviews

River Front house / dock/hot tub

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away.

A cozy outdoor space features a circular arrangement of blue Adirondack chairs surrounding a firepit, set on gravel. A wooden picnic table sits underneath an umbrella, while a spacious green lawn is framed by a wooden fence and trees in the background.
Cottage in Grasonville
4.81 out of 5 average rating, 74 reviews

CoastalBeachCottage*BayViews*Close2WeddingVenues

**Close to all the Wedding Venues** Come relax at the all new Coastal Haven Cottage. Take a nice morning walk to the beach &enjoy your coffee while sitting on a bench overlooking the Chesapeake Bay. Light, bright coastal feel inside the home & enjoy the wonderful outdoor space on the deck or in an Adirondack chair around the firepit. Great outdoor dining space to enjoy crabs or burgers & large yard for the kids to run. 3 Min Drive to The Jetty & many restaurants or walk along the new Boardwalk.

Top guest favorite
An outdoor patio area is featured with comfortable seating options facing a lush green lawn. In the distance, the serene waterfront can be seen, framed by trees. The space offers a peaceful environment for relaxation and social gatherings.
Home in Stevensville
5 out of 5 average rating, 15 reviews

Private Beach Front Marina House

Beautiful waterfront property with private beach shared with one other family, ideal for family gatherings, located within walking distance of Kent Point Marina and convenience store. Enjoy a relaxing evening with family and friends sitting on the outdoor patio overlooking the Chesapeake Bay. You will have exclusive views of fresh-caught crabs & fish as they come off the boats during Summer. If you enjoy crabbing, fishing, boating, kayaking, swimming - it can all be done from this property.

Guest favorite
The renovated cottage features a white exterior with blue accents, surrounded by lush greenery. A small porch with a light blue railing leads to the entrance. A brick pathway and outdoor seating area are visible in the well-maintained yard.
Cottage in Annapolis
4.95 out of 5 average rating, 60 reviews

Charming Waterfront Cottage on Historic Property

Enjoy a peaceful get-away in a beautifully renovated, historic cottage. The 115 acre property is on a peninsula with over 2 miles of shoreline. This charming home has water access, trails, a canoe, a hammock, and a lovely grilling patio. The cottage is on the private grounds of Whitehall Mansion, built in 1764 as the home of Governor Sharpe. The farm is used for horse boarding and private weddings. Nearby attractions include Annapolis, the US Naval Academy, Washington D.C., and Baltimore.

Guest favorite
A serene outdoor space features six Adirondack chairs facing the sunset over the bay. The horizon is lined with soft clouds, and a picnic table is set in the distance on a grassy area, providing a perfect spot for relaxation.
Home in Stevensville
4.91 out of 5 average rating, 64 reviews

Beachside Dream

Kick back and relax in this calm, stylish space, 4 bedroom 3 full bathroom, Sandy Beach front, stunning sunset. An hour from DMV. Wall of windows in the Living Room overlooks the evening sunsets on the Bay. Sun room with the stunning views of bay. Spacious rooms for up to 12 guests($50 charge per guest after 8 guest) 10 minute drive from popular wedding venues, Chesapeake Bay Beach Club and Silver Swan. Hotel quality linens and towels are provided, unlimited High Speed WIFI , 3- Smart TV

Top guest favorite
A charming one-story cottage is surrounded by lush greenery and colorful flower beds. The well-maintained lawn features clusters of lavender-colored flowers, complemented by shrubs and bushes, creating an inviting atmosphere. The front porch, with steps leading up, adds to the home's welcoming appeal.
Cottage in Annapolis
4.94 out of 5 average rating, 32 reviews

Bay View Cottage: Perfect for long or short stays

Peaceful cottage and neighborhood, with relaxing views of the bay, close to Annapolis and shopping. Well equipped kitchen and house for long-term or short-term stays...fenced in yard, screened in porch..beach and kid’s park across the street…quiet and relaxing. Community beach (unguarded) to swim or bring your water kayaks or SUPs. Great place to bike as well. Dining and grocery close by. Enjoy the bay views of boats going by, the sound of birds, and great sunsets. Minutes to Rt. 50.

Guest favorite
A wooden deck area is highlighted with four Adirondack chairs arranged around a central fire table, where flames flicker gently. Beyond the deck, a well-maintained lawn leads to the bay, visible in the distance under a colorful sunset sky.
Home in Stevensville
4.95 out of 5 average rating, 100 reviews

25-50% Off~Private Beach~Hot Tub~Fire Table~

Welcome to our Chesapeake Bay Cottage on Kent Island, Maryland! This unique 3 bed 2 bath home with luxurious amenities is a perfect getaway for families or friends looking to create unforgettable memories and experience all the Bay area offers. Escape the hustle and bustle with an easy commute from Annapolis, Washington and Baltimore. The Naval Academy is right across the Chesapeake Bay Bridge. Adventure and relaxation are within easy reach from any mid-Atlantic and northeastern location.

Top guest favorite
The image captures a serene sunset over the Chesapeake Bay, with warm hues of orange and pink reflected on the water. A silhouette of a boat is seen in the foreground, creating a tranquil atmosphere. The distant horizon merges gently with the colorful sky.
Home in Rock Hall
5 out of 5 average rating, 29 reviews

Sunset at Rabbit Run

Sunset at Rabbit Run is a private waterfront 2 acre property located on the Chesapeake Bay with a semi private beach area and fabulous sunsets. Located just outside of the quaint town of Rock Hall with shade trees in the summer. Fish, crab, kayak and swim in the Chesapeake Bay (weather permitting) while enjoying fabulous sunsets, read a book on the hammock or watch the boats up and down the Chesapeake as they enter Rock Hall Harbor. Your family and/or friends will never want to leave.

Guest favorite
A tranquil view of the Chesapeake Bay is captured, showcasing a grassy expanse leading to the water. Two stone boundary walls are visible, framing the lush landscape. A solitary beach umbrella and chair rest on the shore, inviting relaxation by the calm water.
Home in Annapolis
4.9 out of 5 average rating, 217 reviews

Country House on the Bay

My home (owner occupied/shared) sports a spectacular view of the Chesapeake Bay with access to the beach. The home is spacious with a family, dining, breakfast and living room. Significant kitchen space is available with all of the cookware and place settings you would need for a meal. The master bath is handicapped accessible. My deck can be used for cookouts and relaxation. Hosting a gathering - lets talk- my home is perfect for celebrations. Close to Annapolis & Naval Academy.

Top guest favorite
A serene waterfront scene features a private pier extending over calm waters, bordered by lush green trees. Two Adirondack chairs in the foreground invite relaxation, complemented by a paddle board resting nearby. The soft hues of sunset reflect on the water's surface.
Guesthouse in Grasonville
5 out of 5 average rating, 27 reviews

Quaint Waterfront- access, Private Shorehouse-unit

Location is everything in this comfy and affordable private unit located on the Chester River and Winchester Creek with water views. Also enjoy the hosts private water front amenities such as fishing at our private pier, boating, kayaking, paddle boarding or simply relax at the waterfront for morning coffee and sunrises or enjoy the fire pit in the evening. The community playground and beach are just steps away. Close proximity to restaurants, shopping, trails, and wedding venues.

Guest favorite
A wooden dock extends into a calm river, featuring three red Adirondack chairs at the end. Surrounded by trees, the still water reflects the overcast sky, providing a serene outdoor space for relaxation.
Home in Chestertown
4.98 out of 5 average rating, 60 reviews

Goose Haven, new waterfront house on Fairlee Creek

Goose Haven is nestled on 2 wooded acres on freshwater, Fairlee Creek - about 1.5 hours from Baltimore, Philadelphia, and Washington D.C. It is a very secluded, brand new, 4 BR, 3 BA, waterfront house with direct water access, a dock, and plenty of room to enjoy the outdoors. There is also a public boat ramp/launch right down the road. If you don’t have a boat, don’t worry, we have a kayak & canoe for you to use. Chestertown and Rock Hall are only 20 minutes away.

Top guest favorite
A spacious two-story home is surrounded by lush green lawn and mature trees. A stone path leads to its welcoming entrance. Large windows reflect sunlight, offering views of the nearby water. The serene setting is enhanced by the gentle presence of the surrounding nature.
Home in Chestertown
4.99 out of 5 average rating, 113 reviews

Entire River Front Home - 4 Bedrooms 4.5 Baths

Quiet secluded home on the upper Chester River. All bedrooms on second floor. Master Bedroom with deck and private bath. Bedroom with double bed and private bath. Queen suite with queen bedroom and bedroom with 2 twins with private bath between. For more than 8 guests an inflatable mattress in library near half bath and full bath. Perfect getaway for total relaxation. Water access for kayaking and canoeing. Nine miles from downtown Chestertown.

Popular amenities for Queen Anne's County beachfront rentals