Beach house vacation rentals in Middle River

4.92 out of 5 average rating, 213 reviews

Relax on Kent Island in 3 Bedroom Home w/Waterview

Enjoy your vacation in this Beautiful & Stylish 3 Bedroom Home with a view of the Chesapeake Bay from living room & kitchen! Perfect for Families & Wedding Groups. We are conveniently located to many areas/cities: Annapolis- 20 miles Baltimore- 45 Wash. DC- 50 Easton- 35 Enjoy a Self-Check-in to this Beautiful Home that is perfectly situated near all the local Kent Island Restaurants, Shops, Attractions. This is a Non-Smoking House. Also No Pets, Parties or Large Groups (11 max). Book Today!

5 out of 5 average rating, 26 reviews

Home in Annapolis

Charming Home, Firepit & Fenced Yard in Annapolis!

Relax and enjoy a peaceful visit to Annapolis in my cozy, private beach neighborhood home! The home sleeps up to 8 guests and offers 3 bedrooms, an additional queen mattress pull-out couch, 2 full baths, a full kitchen, laundry area, outdoor firepit and much more ! The space has been designed for your ultimate comfort and relaxation while visiting the historic town of Annapolis. Be sure to take advantage of Cape St. Claire's amazing private beach and some of the best crab cakes in the country!

4.96 out of 5 average rating, 50 reviews

Home in Rock Hall

Eastern Neck Water Paradise w/Brick oven & Beach

This beautiful breathtaking waterfront home is the perfect place for your vacation. This spacious 3 story house sits along the back waters of the Chesapeake Bay, along Grey’s Inn Creek with it’s own private pier and beach area!! Kayaks and paddle boards available for guests to use! The water is 6’-9’ deep depending on the tide. You can bring your own boat or if you’re interested in renting one, Lankford Bay Marina is only 15 minutes by car or boat, must have a MD boaters safety card to rent

5 out of 5 average rating, 34 reviews

Home in Rock Hall

Water Views in Rock Hall

Brand new, custom built home featuring a wall of windows with water views of The Haven on Swan Creek. 3 bedrooms, 3 full baths. Enjoy the screened in porch, sunning yourself on the deck or warming up by the wood stove in the wintertime. Fun tile work in the bathrooms, a giant soaker tub, built in bunk beds (full size), rugs imported from Morocco & lots of original art, brings this home to life! This house is playful & has lots of personality. Walk or bike to all the marinas & eateries in town!

4.95 out of 5 average rating, 19 reviews

Home in Middle River

The Shore House

Come enjoy all Bowleys Quarters has to offer while staying in this beautiful, newly renovated home within walking distance to Miami Beach County Park. This home offers 3 bedrooms, 2 full bathrooms, a laundry room with washer and dryer, a kitchen out of a chef’s dream, a comfortable living room, a spacious front porch, a large backyard and views of the Chesapeake Bay. You’ll be within walking distance to the beach and will be a five minute drive to a handful of local, waterfront restaurants.

4.95 out of 5 average rating, 267 reviews

Home in Grasonville

River Front, Private Single Family Home

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

4.96 out of 5 average rating, 49 reviews

Kent Island Beach House - "Pink" House in Kentmorr

KI Beach House: almost 1800 sq ft. Incredible Water View home across from Kentmorr Beach Bar & Grill/Marina/Fishing Boats near Matapeake State Park & Beach. Perfect for holidays, birthdays, wedding guests, team builds, family fun, fishing, golfing, etc. 4 Bedrooms, 3 Full Baths, 4th Bedroom is large family room with big Internet TVs/fireplace plus a Kitchen, Living/Dining Area, and a huge yard with your very own private beach volleyball court and spacious deck overlooking the Chesapeake Bay.

5 out of 5 average rating, 54 reviews

Bayview Bungalow - Water view, EV charging station

One level living with a view across the Chesapeake Bay of the most amazing sunsets over the Annapolis skyline. Enjoy the large fully stocked kitchen, spacious bedrooms, claw foot tub & separate shower, deck, bbq grill, fire pit, & yard. Take the bikes on the local trails, nap on the hammock, play corn hole, take the beach chairs/toys to the private neighborhood beach, go to one of the many excellent restaurants, visit historic Stevensville, take a trip to Annapolis or DC, & so much more!

4.9 out of 5 average rating, 198 reviews

Home in Annapolis

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.

4.99 out of 5 average rating, 70 reviews

Home in Annapolis

Captain’s Retreat! Newly Renovated - Beach House!

Beautiful newly renovated 3500 square foot 4 bedroom 2.5 bath home located in Arundel on the Bay. Steps to the Beach and a large community playground. With three large decks, enjoy nature, sitting with a glass of wine or coffee in the morning. Gourmet Kitchen opens to a deck with plenty of seating to enjoy outdoor entertaining. Perfect for large groups or multiple families. Custom solid wood bunk beds - Twin XL's over Kings!

4.89 out of 5 average rating, 101 reviews

Home in Pasadena

Beautiful Waterfront Home With Theater Room

This beautiful Pasadena Beach House(Chesapeake Bay waterfront with Pier) private beach access and is in close proximity to Celebrations At the Bay, Fort Smallwood Park, a Golf Course, Mike’s Crab House, BWI Airport, Baltimore, Live Casino, Arundel Mills, Naval Academy, and more. **Swim at your own risk** Every Winter!!! Price Drop!!!!! Enjoy the Same Space at a Lower Rate!!!!! October to March!!!!!!!!