
Family-friendly holiday rentals in Maryland
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Maryland
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

Mad Men Beach House*DogFriendly*7 Min Walk 2 Sea*OUTDOOR MOVIE EXPERIENCE*Private Dock*WORK SPACE*New CRIB
After relaxing at the beach (just a 7 min walk away), unwind on our deck "watchin' the tide rollin' away!" Get the best of the bay & the beach with this dog-friendly hidden gem! Imagine evenings enjoying the bay breeze as you crack crabs on the deck! Relax inside our open-concept great room that allows everyone to be together. Fish on our private dock or use it for your own boat or jet-ski to dock there. Witness spectacular sunsets with our Kayaks. Enjoy a well lit, private work space to virtual work w/ high speed internet! A new wood CRIB now in master suite for restful sleep! The pools and tennis/pickleball courts are only a few blocks away for your enjoyment! Plus, a truly unique OUTDOOR MOVIE EXPERIENCE for all our guests to make for the best Vacay EVER!

Frolic Fields: A Woodsy 14 Acre Homestead w/ Sheep
Easily escape to the woods on a 14 acre homestead that's only 20 miles from DC. Surrounded by the forest with amazing views, designed by artists, this secluded hideaway is a celebration of Nature and Art. Recharge amongst these ancient trees and all the singing critters that soundtrack the night. Enjoy a fire, frolic in the fields, read on a hammock, strum a guitar, and feel the pressure of modern life melt away. Explore the many bucolic trails nearby. Perfect for retreats and workshops.

Cabin on Middle Creek - Myersville MD - Middletown
Park the car & walk across the creek on the foot bridge to serenity along Middle Creek. Nestled between South Mountain State Park & Gambrill State Park, lies a beautiful & relaxed 9-acre private cabin retreat. Great place to unwind & de-stress. Let the sound of the creek or rain on the tin porch roof put you to sleep at night. It has all the essentials of home. Enjoy the fire pit on cool evenings or take a dip in the stream on a warm day. The cabin offers a perfect peaceful or romantic setting

Sleepy Hollow Log Cabin
Sleepy Hollow Log Cabin at Beechnut Springs is nestled in the majestic Blue Ridge Mountains. A short distance from Rt 70 as you travel down scenic route 17 following a bustling trout stream to Beechnut Springs entrance. After you arrive & settle into your secluded cabin, you will find many unique activities & quiet places in this serene setting amid the wonders of quiet waterfalls, easy walking paths, a wildlife haven, natural running streams & "The Bog Shack". Welcome to Sleepy Hollow Log Cabin

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

Kone Oasis- hot tub, pool, theater/game rm.
Have fun and relax at this stylish oasis! Packed w/ amenities. Huge Pool w/multiple cabanas, HOT TUB, trampoline, playground, axe throwing, pool/ice hockey table, arcade,huge theater room and outdoor projector too, basketball court, grill, spa/library with sauna and full gym!! 5 comfy beds. Rooms split for privacy. Open kitchen/dining/living room. Cold DeerPark water fountain. Basement apt so there is some movement noise. Updated bath and an outdoor shower. 20 mins from DC & National Harbor

Luna the Destination Camper
Just outside the buzz of D.C., Chesapeake Hideaway offers a peaceful, romantic retreat in the heart of Lanham. Surrounded by the natural beauty of Prince George’s County, this cozy RV features a queen+full bed, soft lighting, and panoramic windows for golden sunset views. Enjoy intimate meals in the charming kitchenette, then unwind on your private deck. Whether you're stargazing or exploring nearby Lake Artemisia and Greenbelt Park, this is the perfect spot to relax and make lasting memories.

Private guest suite in a newly remodeled home
We welcome you to a spacious and private basement apartment with its own entrance and self check-in. Get cozy with your guests in a space that has a bedroom with a king-size bed, an 85-inch smart TV, soft sectional , private toilet, bathroom and kitchenet, all in the same space. None of the amenities are shared. The fully-equipped kitchenet has everything you'll need to cook and warm your meals. Guest suite is the entire basement apartment which is a part of a bigger home where host lives.

Creekside Retreat at the Jewel Vinsota
Relax in a quiet, curated, pet-friendly art exhibit. Live with paintings & sculptures that are for sale. This garden apartment is tucked into a hillside above a creek, along the Jewel Vinsota Sculpture Trail. Your host/gallery curators live upstairs. The “Artist’s Guesthouse” is next door. The private entrance is down a stone-stepped path. Perfect for 2 w/ the queen bed but room for 3 w/ the living room futon. Fully equipped kitchen. Private charcoal grill and fire pit next to the creek.

Spruce Run Cottage, Farm stay on Catoctin Mountain
The cottage is located on 25 acres of mostly wooded terrain off Highway 17 near Wolfsville, Maryland, less than an hour and a half from D.C. The cottage faces the woods and the private drive down to the creek. There is almost zero light pollution at night so stargazing is incredible from the balcony. The hosts live on the property up the hill in an 1890’s chink log cabin. Although you can see our house, the cottage feels very private and is a quiet comfortable retreat in the hills.

Adorable Waterfront Apartment Weekend Getaway
Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

White Point Cottage -- Quiet Waterfront Getaway
Welcome to White Point Cottage on the beautiful Potomac — 90 minutes from Washington, DC, but a world away. The renovated 2 bedroom, 1 bath cottage sits on nearly an acre of south-facing waterfront property, affording a sense of privacy along with sunrise and sunset views. We’ve owned in the same neighborhood in St. Mary's County since 2005 and are eager to show guests why we love it here. Be sure to visit our sister property, Water's Edge Cottage.
Popular amenities for Maryland family-friendly rentals
Family-friendly home rentals with a hot tub

Romantic Getaway In The Pines. Hot Tub! King Bed!

Cozy Cottage, Winter Promo, Hot Tub, BlockToBeach

Peace Point - Waterfront, Secluded, Home w/hot tub

Sauna, hot tub, great outdoor space!

Treehouse in Deep Creek Lake

Wigwam Lodge ~ HotTub ~ MasterSuite~Woodland Views

The Overlook; A Romantic Treehouse for Two

Luxe Winter Retreat- 5 Star
Family- and pet-friendly home rentals

Spacious, Private Basement Apartment

Riverfront Chalet Kayak/Canoe, pier, breakfast!

* Spacious Private Suite Full of Style & Comfort *

Glen Burnie Escape

“Cabana by the Bay”-tiny home on a pier!

Fox Cottage *Pet Friendly*

Home away from home

Historic Downtown in-law suite
Family-friendly home rentals with a pool

Beach Paradise 202-Downtown Luxury Condo Bay View

Sophisticated Studio Apartment, Metro DC

Rollingside: Two-Room Guest Suite

Affordable, Cozy Retreat 4 Miles from Annapolis

Gunpowder Retreat

1st Floor Condo in Annapolis

Beachfront with a View and Amenities Galore

The Little Gypsy BoHome
Destinations to explore
- Houseboat rentals Maryland
- Flat rentals Maryland
- Cottage rentals Maryland
- Treehouse rentals Maryland
- Boat rentals Maryland
- Resort rentals Maryland
- Beach apartment rentals Maryland
- House rentals Maryland
- Beach house rentals Maryland
- Cabin rentals Maryland
- Beachfront rentals Maryland
- Aparthotel rentals Maryland
- Lakehouse rentals Maryland
- Mansion rentals Maryland
- Rentals with an accessible-height bed Maryland
- Rentals with beach access Maryland
- Rentals with an EV charger Maryland
- Campsite rentals Maryland
- Fitness-friendly rentals Maryland
- Bed and breakfasts Maryland
- Rentals with a fireplace Maryland
- Rentals with a washing machine and dryer Maryland
- Townhouse rentals Maryland
- Rentals with a hot tub Maryland
- Tent rentals Maryland
- Apartment rentals Maryland
- Rentals with a sauna Maryland
- Loft rentals Maryland
- Private suite rentals Maryland
- Motorhome rentals Maryland
- Barn rentals Maryland
- Rentals with a kayak Maryland
- Rentals with pools Maryland
- Villa rentals Maryland
- Serviced apartment rentals Maryland
- Hotel rooms Maryland
- Dome rentals Maryland
- Waterfront rentals Maryland
- Pet-friendly rentals Maryland
- Rentals with breakfast Maryland
- Rentals with a firepit Maryland
- Rentals with a patio Maryland
- Guest house rentals Maryland
- Tiny house rentals Maryland
- Chalet rentals Maryland
- Holiday home rentals Maryland
- Rentals with outdoor seating Maryland
- Farm stay rentals Maryland
- Rentals with an accessible-height toilet Maryland
- Boutique hotels Maryland
- Rentals with a cinema Maryland
- Rentals with lake access Maryland
- Smoking-friendly rentals Maryland
- Ski-in/ski-out rentals Maryland
- Family-friendly rentals United States
- Things to do Maryland
- Nature and outdoors Maryland
- Food and drink Maryland
- Art and culture Maryland
- Sightseeing Maryland
- Tours Maryland
- Things to do United States
- Entertainment United States
- Art and culture United States
- Food and drink United States
- Sports activities United States
- Wellness United States
- Tours United States
- Nature and outdoors United States
- Sightseeing United States




