Family-friendly holiday 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 favourite

Apartment in Pasadena

4.99 out of 5 average rating, 550 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.

22 Feb – 1 Mar

$1,135 AUD total

Guest favourite

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!

19 – 26 Aug

$2,063 AUD total

Guest favourite

Guest suite in Laurel

4.98 out of 5 average rating, 173 reviews

Whiskey Bottom Saloon by LLOYD SUITES

Whether you're a service member transferring to the area or here for business or pleasure, our 'Saloon' themed apartment is the perfect retreat. We're 25 mins from DC and 20 mins from Baltimore. Just a gallop to I-295, I-95 and Fort-Meade. Are you flying in from BWI Airport? We are only 15 mins away. If you would like to try your luck, we are 20 mins from Maryland LIVE Casino and Horseshoe Casino. Within walking distance is the famous Laurel Park Horse Race Track with live & simulcast races.

13 – 20 Nov

$1,452 AUD total

Guest favourite

Guest suite in Arnold

4.96 out of 5 average rating, 567 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!

22 – 29 May

$2,224 AUD total

Guest favourite

Home in Glen Burnie

4.97 out of 5 average rating, 397 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.

25 July – 1 Aug

$2,043 AUD total

Guest favourite

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.

13 – 20 Aug

$1,216 AUD total

Guest favourite

Guest suite in Chestertown

4.99 out of 5 average rating, 192 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.

13 – 20 Sept

$1,660 AUD total

Guest favourite

Apartment in Crownsville

4.98 out of 5 average rating, 165 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.

21 – 28 Oct

$1,187 AUD total

Guest favourite

Cottage in North East

4.97 out of 5 average rating, 443 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.

16 – 23 Apr

$1,294 AUD total

Guest favourite

Guesthouse in Highland

4.98 out of 5 average rating, 264 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.

18 – 25 Oct

$1,392 AUD total

Superhost

Apartment in Baltimore

4.79 out of 5 average rating, 463 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.

7 – 14 Oct

$1,048 AUD total

Guest favourite

Townhouse in Baltimore

4.95 out of 5 average rating, 570 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 adventurous single traveler. Luxury touches include a walk-in rain shower with separate bathtub, bathroom vanity station, 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.

27 Mar – 3 Apr

$2,090 AUD total