Kid-friendly holiday rentals in Maryland

Cozy 3 BR Pet Friendly Beach, Bay & Pond nearby.

Relax with the family in this comfortable and charming home. There is room for 8 to sleep comfortably. The dining room and breakfast nook offer plenty of seating for all with a spacious kitchen. Our corner lot offers the option for outdoor fun like slip and slide, corn hole, frisbee, and more! Nearby: Beach, Bay, Wildlife sanctuary surrounded by a walking trail, Pool, Tennis, restaurants & Eventful Northside Park! Quiet and peaceful location to make family or romantic memories of a lifetime.

Club Carp North Beach - Steps to the Bay!

Calendar open for bookings in April 2025! Welcome to Club Carp North Beach. A charming and cozy cottage just 3 blocks to the Boardwalk/Beach. Renovated throughout with 3 bedrooms and 2 full baths. Perfect place for a relaxing, family vacation! This kid-friendly home has a large fenced side yard with swing set, play area for the kiddos, and lots of extra amenities with families in mind. Comfortable outdoor dining area with fire pit and gas grill. Just steps to restaurants, shopping, and bars.

Hot tub, Pool table+darts, near ski resorts

Your family will be close to everything when you stay at this centrally-located place. Quiet neighborhood and comfortable settings ** NO PARTIES ** Plenty of room to enjoy a getaway with friends and family without the headache of inconveniences. Basketball hoops on the driveway and pool side. Dart board and pool table offer indoor activities when the weather doesn't want to cooperate. Multiple HD t.v's for your viewing pleasure and HDMI connections to connect a gaming console of your choice.

Koi House

Relax with the whole family at this peaceful place to stay. Minutes away from Pocomoke River State Park. Close to Historical Snowhill. Only 26 mins to Assateague Island where you will see wild horses running free. From Assateague Island you can go to Historical Berlin where you can see the Atlantic Hotel where the movie Run away Bride was made. Enjoy a bite to eat at The Box Car restaurant. Then go have some homemade ice cream at the famous Island Creamery. So much more to do.

El Ancla

stunning bay sunsets and idyllic outdoor space at this peaceful waterfront home in prime 94th street location with amazing breeze. Recently rehabbed - new hardwood floors, bathroom, and brand new interior and exterior furniture. Bayfront deck with your own boat slip. Brand new casual comfort deck furniture. Remote work with a view! 10 min walk to beach, playground, community arts center, mini golf, bars. Beach chairs included. We can provide pack n play upon request

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

Beachfront Oasis with Amazing Views

Perfect getaway home to relax and enjoy peaceful beach views. This beachfront home is perfect for a romantic weekend getaway or a family vacation. Enjoy long walks on the beach, conversations at the fire pit in the evening, kayaking or hunting for fossil sharks teeth. The perfect escape from DC, the home is just over an hour from the city and located in the quiet, private beach community.

Quiet Waterfront

Waterfront guesthouse in gated community on a creek off of the Severn River with clubhouse, swimming beach, tennis court. Approximately five miles from downtown Annapolis. NO PETS, NO SMOKING, NO PARTIES. Parking for up to four cars only. Anne Arundel County License Number STR-120.

Rockfish Keeper

Relax with the whole family at this peaceful place to stay a quarter of a mile from the center of town. Open floor plan with kitchen, living room and sun room. Sleeps 9 with 2 full bath and bonus outdoor shower. Large back fenced in backyard with pool.