Family-friendly holiday rentals in North Beach

Quiet Coastal Cottage Escape with Water Views

Want to get away? Come relax and escape in our updated bay view cottage. You'll enjoy stunning sunsets, warm surroundings, and all the amenities you could want in our cozy, peaceful cottage home. You'll find plenty of comfortable spots to relax, inside and out. Located on a quiet street, while still close to the small-town charm and offerings of North Beach, Chesapeake Beach, and Herrington Harbor. Walk along the bay, enjoy the local restaurants, and get ready to relax. Stay a week and save!

Walk to Beach! King Bed & Free Beach Passes

Welcome to Bay Haven at A Haven Away! Relax in a fully-equipped, plant-filled oasis with a king bed primary suite that our guests love. Its prime location is in walking distance to the beach, restaurants, fresh seafood, and wetlands. We’ll share our beach passes and lots of local recommendations so you can enjoy our little slice of heaven. 12 min walk to the beach, boardwalk, restaurants, and kids play areas in cute North Beach, MD 7 min drive to Herrington Harbor 14 min drive to Tacaro Estate

Warm Home Overlooking the Chesapeake Bay

Sitting on the Chesapeake Bay, North Beach is a town where you are so close to things, yet can feel so far away. Only 45 minutes form Washington, DC, you can sit on one of three decks and gaze into the Chesapeake Bay, enjoying all that small town life has to offer. An open plan, with defined spaces, the house is at once cozy (with a fireplace) and spacious for a family. It is great for couples, adventurers, business travelers, and families. This is not a house for large groups or parties.

Bayside Oasis of Southern Maryland

1 1/2 blocks from the beautiful Chesapeake Bay. Walk to boardwalk, restaurants and shopping. Beach opens, with some restrictions, May 28, 2021. Free beach pass provided. Quiet friendly town where everyone knows your name. King bed, private bath with shower (no tub). Free WiFi, private off street parking, 45” TCL-Roku TV, Echo Dot, Keurig w/pods for coffee and tea, full kitchen (no dishwasher), beach chairs, beach towels, dishes, flatware, pots pans. Chesapeake Beach is 1-mile south on Rt 262.

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.

Cass-N-Reel Luxury Houseboat

Kent Narrows Rentals Welcomes you aboard Cass-N-Reel! A 432sqft luxury getaway in the Kent Narrows. With 1 bedroom, 1 bathroom, and a gorgeous covered rear facing deck; this is the ultimate couples retreat! 9 waterfront/waterview bars/restaurants within walking distance! Get a taste of what the eastern shore has to offer. Minutes from the Chesapeake Bay Bridge and a short drive to Annapolis, D.C., St. Michaels, and Ocean City. Come stay and live like a local! NO Fishing/Crabbing on property

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l dates**

Chill in The Crib! Easton, Maryland

Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for ONLY TWO INDIVIDUALS (No children under 8 years of age.), and please limit your visit to one vehicle only.

Peaceful Waterfront Retreat on The Bay

Escape to a serene waterside cabin with a private dock on quiet St. Leonard Creek, just an hour from Washington, DC. This rustic studio offers a cozy retreat for solo travelers, couples, or small families looking for peace and relaxation. Whether you're here to unwind, work remotely, or explore the outdoors, you'll find plenty to enjoy—including two kayaks, two canoes, and stunning waterfront views.

Nice Guest Suite at Chesapeake Bay

Take it easy at this unique and tranquil getaway. Come and relax in our modern & comfortable guest suite to enjoy a small-town quiet setting with amazing Chesapeake Bay views. A short drive from Washington DC (45 min), Annapolis (30 Min), or Baltimore (1 hr). Groceries, boardwalks, restaurants are all within walking distance. Enjoy cable TV, high-speed Internet, and strong wifi through Xfinity.

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, a basketball hoop, beach access, a canoe, a gas grill, a steam shower, and an outdoor redwood infrared barrel sauna.

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.