Kid-friendly vacation rentals in Somerset County

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Somerset County

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

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Guest favorite

Home in Smith Island

5 out of 5 average rating, 10 reviews

Discover Smith Island! (But breakfast first)

Welcome to The Ungovernable Goose! My name is Luci, but my dad called me "Goose", and I've always been a bit of a rebel. The philosophy here is simple: Do whatever brings you joy! Stay up late. Sleep in. Take naps. Eat the cake. Drink the good stuff. Speak your mind. Live fiercely. Read banned books. Go barefoot. Spark a revolution. Become ungovernable... Let us help you discover all of the history, culture and natural beauty Smith Island has to offer. Recreation Packages Available!

Superhost

Home in Princess Anne

4.79 out of 5 average rating, 19 reviews

Ye Ole Pirate House

Legend has it that this whole unique area was once inhabited by pirates! Surrounded by nature, not to mention the starry sky at night, this house is the embodiment of the life and spirit of all that have been fortunate enough to experience the tranquility and beauty this area offers. Our home here is spacious and quiet! Surrounded by nature, trees, nearby beach to enjoy sunsets and best of all the simple songs of the birds. Bring your fishing pole, boat ,kayak , yoga or meditation mat!

Guest favorite

Cottage in Westover

4.99 out of 5 average rating, 205 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

Winter time is a great time at Rumbley! Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all window. Look out to the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Wifi, Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

Guest favorite

Home in Deal Island Historic District

4.93 out of 5 average rating, 28 reviews

House of the Setting Sun/Deal Island Bayfront Home

Soak up the quiet beauty of Tangier Sound at this bayfront getaway with stunning sunset views among the pines. Enjoy crabbing, fishing, and swimming off the dock. Dive into nature photography, birdwatching, hunting, kayaking in the wetlands, and more. There's a small local beach less than 5 minutes away. It's far enough away to unplug, but less than an hour to Ocean City, Chincoteague, and Assateague. And there's plenty to enjoy onsite, including sunsets 9 months out of the year!

Guest favorite

Rental unit in Crisfield

4.95 out of 5 average rating, 55 reviews

Stylish Condo With A Great View

This unique place has a style of its own. Beautiful furnishings and arts throughout and comfort and peace within. Its location is impeccable provided that it has the best view in town. Short walking distance from Crisfield’s dock where you can fish and enjoy sunsets. It’s also steps away from where the cruises dock and take sail. Just a few short miles from the towns incredible restaurants and convenient dollar stores. Enjoy sunrises and sunsets on the one of a kind deck.

Guest favorite

Home in Crisfield

4.96 out of 5 average rating, 275 reviews

Cozy Home near Waterfront in Crisfield, MD

Our home is close to great views, restaurants and shopping, the beach and family-friendly activities. You’ll love the sunsets over the water and viewing working boats in the harbor. Great for couples, solo adventurers, business travelers, and families (with kids). Beach is walking distance and the boat launch is 1/2 mile away. New library, playground, fishing, crabbing and gorgeous sunsets are all close by. Owners live only 15 minutes away for anything you may need.

Guest favorite

Guest suite in Crisfield

4.74 out of 5 average rating, 188 reviews

The Serenity House

Regenerate at the Serenity House! Second floor apartment; three spacious queen bedrooms with SmartTV, equipped kitchenette, work space with WiFi, mudroom and laundry on the first floor. Large yard with big mature shade trees nestled in a quiet neighborhood. One corgi and two cats live on the property. The pets are not allowed into the guest rooms. Continental breakfast served in the shared space. Private entrance, off street parking available.

Guest favorite

Home in Deal Island Historic District

4.95 out of 5 average rating, 21 reviews

Rusty Anchor

Escape to the Rusty Anchor, a beautifully restored 1900s farmhouse on Deal Island, MD! With 3 cozy bedrooms, it's perfect for families or friends. Just around the corner, enjoy a cozy beach, crabbing, and easy access to fishing (Redfish, Striped Bass, Flounder) and waterfowl hunting. Only a 5-minute bike ride to beaches and boat ramps. Book now and receive a link to our store to reserve add-ons or schedule special experiences for your stay!

Guest favorite

Cottage in Westover

4.93 out of 5 average rating, 171 reviews

Heaven on the Bay - A Peaceful Waterfront Retreat

This Chesapeake Bayfront cottage has spectacular views to take you away from everything in any season. It boasts more than 120 feet of waterfront, and you can dangle your feet off the 70 ft “dock of the bay”. Launch kayaks from the small sandy beach in summer, or cozy up to the wood stove in the winter. Inside, you’ll find wood floors throughout, modern kitchen & baths with bay views from every room. Kayaks, SUP, bicycles & crab traps too!

Guest favorite

Guesthouse in Deal Island Historic District

5 out of 5 average rating, 27 reviews

Blue Crab Bungalow

Leave the hustle and bustle behind as you relax and refresh in this spacious 1 bedroom, 2nd floor waterfront property. Enjoy amazing sunsets, tons of stars, and the sound of the water from the large deck, private pier, or around the fire pit. Try crabbing or fishing from the pier. No license needed! A small local beach and public boat ramp are less than 5 minutes away. We are about an hour to Ocean City, Chincoteague, and Assateague.

Superhost

Cottage in Saxis

4.86 out of 5 average rating, 215 reviews

ISLAND SUNSETS Near Chincoteague Island

1 - Story Near Chincoteague Island Virginia Assateague Beach NASA Wallops Island, Va. Onancock, Va Waterman’s Fishing Village Surrounded by Water on three sides & Virginia Wildlife Refuge on fourth side. 400 ft. Walking distance to Beach, Kayaking & Canoeing, Wildlife, Fishing Pier, Boat Ramp, Marina, Public Pavilion, Ice Cream Shop, 2 Restaurants, Museum, Multiple Seafood Shantys

Guest favorite

Guest suite in Deal Island Historic District

4.9 out of 5 average rating, 105 reviews

Private guest suite near Deal Island Maryland

Nothing extraordinary here. What I have available, at a reasonable rate is a clean private suite. With self check-in using kwikset smart code touchpad electronic deadbolt. Private driveway with plenty of room for your truck and boat. Room and deck are handicap accessible using entry ramp or steps.