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

Rental unit in Upper Fells Point

4.86 out of 5 average rating, 813 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.

Guest favorite

Guesthouse in Glenwood

4.95 out of 5 average rating, 177 reviews

The Caretaker's Cottage-Historic Roundabout Hills

The Caretaker's Cottage was built in the 1770s by Ruben Merriwether, and sits near the manor house where he and his ancestors lived at Roundabout Hills. An exceptional space with a fabulous full kitchen perfect for those who like to cook, it is truly a one of a kind place to stay. The house, where John and Fiona live, and the cottage are secluded and private, but close to all of the art, culture, restaurants and dining in the nearby towns of Frederick, Columbia, Baltimore, and Washington, DC.

Guest favorite

Guest suite in Arnold

4.95 out of 5 average rating, 622 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 favorite

Bungalow in Baltimore

4.98 out of 5 average rating, 246 reviews

Cozy Retreat Bungalow 20min to downtown 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!

Guest favorite

Home in Glen Burnie

4.97 out of 5 average rating, 424 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 favorite

Serviced apartment in Pasadena

4.98 out of 5 average rating, 587 reviews

Sea Dreamer

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 favorite

Guest suite in Hampden

4.92 out of 5 average rating, 357 reviews

Cozy Private Suite with City Charm & Parking!

This private, cozy suite is designed specifically for Airbnb travelers. With hotel room amenities, you'll feel comfortable right away! A private entrance with no stairs is accessed by a short path from your reserved parking in the driveway. Located in Hampden, an extremely vibrant neighborhood, yet so close to everything else Baltimore City has to offer. Only 25 min from BWI. The space is good for couples, solo adventurers & business travelers. Please read property details prior to booking.

Guest favorite

Guest suite in Fells Point

4.91 out of 5 average rating, 654 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.

Guest favorite

Guest suite in Catonsville

4.94 out of 5 average rating, 501 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 favorite

Guest suite in Chestertown

4.99 out of 5 average rating, 213 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 favorite

Townhouse in Upper Fells Point

4.95 out of 5 average rating, 628 reviews

Romantic Hot Tub Getaway, Walk to Fells Point

Located on a quiet street in a safe neighborhood, this one-bedroom Baltimore rowhome is ideal for a couple or single traveler. Luxury touches include a walk-in rain shower with separate bathtub, wide variety of soaps, shampoos and essential toiletries, gourmet coffeemaker, outdoor hot tub, private washer/dryer, ultra-plush bedroom carpet and more. Blazing fast wifi, free premium streaming, coffee, teas, clean linens and more are also included with your reservation.

Guest favorite

Rental unit in Patterson Park

4.8 out of 5 average rating, 499 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.