Family-friendly holiday rentals in Rock Hall

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Rock Hall

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Guest suite in Arnold

4.96 out of 5 average rating, 589 reviews

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

Guest favourite

Serviced apartment in Pasadena

4.98 out of 5 average rating, 569 reviews

Sea Dreamer aka Phenomenal Hospitality

Tranquil, riverfront, SPLIT LEVEL home, rental is downstairs. 1 bedroom and a patio room can be a 2nd bedroom or living room with 2 pullouts. 3rd space is the Living room with large TV, sleeper sofa, dining and office space, recliner and massage chair! Bath has stand up shower with awesome showerhead, soaps, shampoos, hairdryer and towels. Kitchenette has everything necessary to cook with. BWI 25 min, 45 Annapolis, 60 to DC. Patio , table, grill, lounging sofa, kayaks and beach walks.

Guest favourite

Home in Glen Burnie

4.97 out of 5 average rating, 413 reviews

Secluded acre near BWI and Baltimore

Secluded suburban acre 8 minutes from BWI Airport, 15 minutes from Baltimore's Inner Harbor and from Fort Meade, and 45 minutes from Washington DC. Private house attached to host house has 1220 square feet of cozy comfort--4 times the size of a hotel room! House includes 2 bedrooms (one queen, one double), 1.5 baths, living room, foyer, dining room, full kitchen, and washer/dryer. The one-acre lot has hundreds of trees and is great for pets. Level 2 charging station is good for all EVs.

Guest favourite

Cottage in Rock Hall

4.99 out of 5 average rating, 103 reviews

Cottage by the Bay in Rock Hall, MD

Sunny cottage in quiet waterside town of Rock Hall. Easy walk into downtown: grocery store, cafe, gift shop with beautiful housewares, gifts and jewelry, styling salon, quilt shop, ice cream shop, and local produce market. Gas fireplace, screened porch, stone patio, deck, several bicycles, tv for dvd's. Restaurants, crabs, Eastern Neck Wildlife Refuge, and nearby Tolchester and downtown Chestertown. Public pool, small beach (& picnic gazebos), bike around town...come to relax year round!

Guest favourite

Cabin in Chestertown

4.98 out of 5 average rating, 223 reviews

Rivershore Retreat

Escape to Maryland’s Eastern Shore where the pace of life is slower and nature surrounds you. Mid-century modern A-frame with artfully curated décor and a well-appointed kitchen has drop-dead gorgeous river views and its own waterfront and dock. The house sits on a large, private acre lot with plenty of room for kids to play. Short walk to downtown Chestertown with its Farmer’s Market, restaurants and galleries. A perfect get-away for artists, writers or families seeking a low-key vacation.

Guest favourite

Guest suite in Catonsville

4.94 out of 5 average rating, 483 reviews

Rollingside: Two-Room Guest Suite

Two-room guest suite with private entrance located in picturesque Catonsville, MD on a pre-Colonial road originally used for rolling tobacco to the harbor. Downtown Baltimore is 20 minutes away, BWI airport and Amtrak station 15 minutes, and our street is located on a bus route. Beautiful 3.5 mile walk to historic Ellicott City and an hour from Washington, D.C. Individuals and families with children are welcome, but the Airbnb member renting the property must be over the age of 25.

Guest favourite

Guest suite in Chestertown

4.99 out of 5 average rating, 202 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront apartment/guest suite conveniently located minutes from historic Chestertown and Washington College. Beautiful water views, full kitchen, wooded lot, quiet neighborhood, bird watching, biking, running, kayaking. Friendly pets (comfortable with people and our medium rescue dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice. Make it your home away from home.

Guest favourite

Rental unit in Crownsville

4.98 out of 5 average rating, 173 reviews

“River Sweet" Private Apartment

River Sweet has everything you need for a fun and relaxing getaway. Cozy and clean, River Sweet provides all the comforts of home, including your own driveway and entrance. You'll delight in privacy while enjoying a safe, waterfront neighborhood. A local mini mart and restaurant are close by. And, you are centrally located between Annapolis, Baltimore and Washington for fun excursions! Please let us know if you need a long-term stay. We would be happy to accommodate you.

Guest favourite

Guest suite in Arnold

4.85 out of 5 average rating, 525 reviews

Sunny Spot Suite, Serene, Annapolis, Naval Academy

Clean, bright, private and spacious guest suite, downstairs in home. The space is a living room, bedroom and bath. Private entrance, self check-in and peaceful seclusion. Dark, quiet bedroom. Living area has a futon (topper in the closet). TVs and Netflix in both rooms - 55" in living area, Cleaned and disinfected. Both rooms have separate access to the bathroom. There is a lovely, lush view out the back. Self check-in. Safe neighborhood, close to trails and river.

Guest favourite

Guest suite in Upper Marlboro

4.95 out of 5 average rating, 109 reviews

Private Apartment on a Horse Farm

My place is convenient to Joint Base Andrews (20 minutes), Washington DC and Annapolis MD (both are about 40 minutes by car) but you’ll love my place because of the outdoor space and the peace and quiet. For Equestrians, we are within 10 minutes of the Prince George's Equestrian Center as well. My place is good for couples, solo adventurers, families (with kids), and well-behaved pets. With a full-sized kitchen, this apartment is a great home away from home.

Guest favourite

Guest suite in Edgewater

4.9 out of 5 average rating, 463 reviews

South River Park Apartment

Located minutes from Annapolis, MD the in-law apartment offers access to Baltimore and DC in under an hour. The apartment offers its own entrance, full kitchen, one bathroom, one bedroom, tile floors, pullout sofa, Wifi, and parking. The apartment is registered with the Anne Arundel County Dept. of Inspections & Permits, #STR-15, for short term rentals.

Guest favourite

Guest house in Havre de Grace

4.89 out of 5 average rating, 227 reviews

Studio apartment with off street parking

Private studio apartment just minutes away from the mouth of the Chesapeake Bay. Visiting our small town of Havre de Grace for a wedding or a local event, choose to relax in our sports themed comfortable home away from home. Havre de Grace has a lot of wonderful events, shops and restaurants to offer, and you will be just steps away from them.