Family-friendly vacation rentals in Essex

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Essex

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

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Guest favorite

Apartment in Pasadena

4.99 out of 5 average rating, 547 reviews

Sea Dreamer aka Phenomenal Hospitality

Stunning sunrises free in a tranquil, riverfront, apartment with front entrance. Split foyer home, I am upstairs, you are downstairs. 2 separate bedrooms, one overlooking the river. Living room includes dining area, office space, comfy seating, and a massage chair!. Full bath, best showerhead, soaps, shampoos, and towels. Pull out sofa bed for larger parties. Kitchenette has everything necessary to cook with. BWI 20 min, 40 Annapolis, 60 to DC. Patio, fire pit, grill, deck and beach walks.

Sep 30 – Oct 7

ﺩ.ﺇ353 per night

Guest favorite

Apartment in Baltimore

4.86 out of 5 average rating, 784 reviews

Stay in a Former Fells Point Bar! - Private Studio

Rent a unique studio apt in Fells Point! This is no cookie-cutter Airbnb. We converted a portion of our home, a 19th century construction & mid-20th century Fells Pt bar, into a 500 foot apartment w/private entrance, bathroom, work & living space. The apartment is near Fells bars & restaurants, Canton, Hopkins, the harbor, Patterson Park & downtown. 2 miles from stadiums. There is a 6 in. incline from sidewalk to entrance. Access ramp available. We only host via Airbnb. No 3rd party bookings.

Mar 14 – 21

ﺩ.ﺇ257 per night

Guest favorite

Guest suite in Arnold

4.96 out of 5 average rating, 565 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!

Jul 11 – 18

ﺩ.ﺇ419 per night

Guest favorite

Bungalow in Baltimore

5.0 out of 5 average rating, 231 reviews

Cozy Eclectic Retreat Bungalow 20min to Baltimore

Welcome home! Whether you are in town for business or leisure, this home will meet your needs at a very competitive price, and we are only 20 minutes from downtown Baltimore. If you're looking for a clean, comfortable, airy, and memorable home for your trip, congratulations, you just found it! No more worries about finding parking, handling the noise from neighbors above or below you, or sharing the house with anybody else. The entire house is all yours to enjoy. You will enjoy your stay here!

Nov 22 – 29

ﺩ.ﺇ587 per night

Guest favorite

Home in Glen Burnie

4.97 out of 5 average rating, 396 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.

Aug 22 – 29

ﺩ.ﺇ497 per night

Guest favorite

Guest suite in Baltimore

4.91 out of 5 average rating, 584 reviews

Secret Garden in the City

Art is everywhere! Most walkable part of Bmore! We are hosts with the inside scoop on the city. Close to everything! 25 minutes to airport (~$35 Lyft/Uber) 15 minute walk to InnerHarbor and 10 minute walk to many restaurants, bars, and boutiques. To get to the: National Aquarium/Inner Harbor (main tourist attraction) 0.6 miles, Marriott Waterfront Hotel/Conference Center 0.5 miles, Johns Hopkins Main Hospital 1.2 miles, Baltimore Convention Center 1.3 miles, and 2.6 miles to Penn Station.

Oct 13 – 20

ﺩ.ﺇ367 per night

Guest favorite

Guest suite in Catonsville

4.94 out of 5 average rating, 470 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.

Sep 6 – 13

ﺩ.ﺇ363 per night

Guest favorite

Guest suite in Chestertown

4.99 out of 5 average rating, 191 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.

Sep 13 – 20

ﺩ.ﺇ523 per night

Guest favorite

Apartment in Crownsville

4.98 out of 5 average rating, 164 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.

Jun 28 – Jul 5

ﺩ.ﺇ472 per night

Guest favorite

Cottage in North East

4.97 out of 5 average rating, 440 reviews

Persimmon Pastures

A quiet country setting in North East MD..located on a 7 acre horse farm with easy access to I95. Enjoy all the serenity of the country yet close to the shopping, marinas, and within 50 mile access to Baltimore, Wilmington and Philadelphia. The property is also within 30 minutes of Fair Hill Natural Resources Area with 5,500+acres and 80+ miles of trails for hiking, biking, and beautiful scenery. Pets are allowed. A pet (dog/cat) fee of $5/night/pet will be requested.

Mar 17 – 24

ﺩ.ﺇ415 per night

Guest favorite

Guesthouse in Highland

4.98 out of 5 average rating, 263 reviews

Woodland Retreat

Welcome to our private woodland retreat! This stylish and secluded mid-century modern guesthouse is nestled on five acres in horse country in Highland, Maryland. Totally separate from our owners home, our guesthouse combines the serenity, privacy, and safety you crave with all the conveniences of modern life including: a full bath; kitchenette; internet; and a screened porch with access to our beautiful lighted and heated swimming pool and adjacent walking trails.

Sep 18 – 25

ﺩ.ﺇ448 per night

Superhost

Apartment in Baltimore

4.79 out of 5 average rating, 462 reviews

Pagoda House

The Pagoda House is a 1 BR basement apartment with a private entrance and bright window! The unit has new floors, an open layout, and plenty of living space. Our location is perfect for exploring the neighborhoods of Butchers Hill, Canton, and Fells Point. The waterfront promenade is reachable on foot and provides access to many of Baltimore's best sights. Patterson Park (one of the top city parks in the nation) is located directly across the street.

Jul 3 – 10

ﺩ.ﺇ318 per night