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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 suite in Crisfield

4.7 out of 5 average rating, 145 reviews

The Serenity House

Regenerate at the Serenity House! Second floor apartment; three spacious queen bedrooms with Hulu TV, 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 dog is tied to the shed and the cats like to lounge on the steps. The pets are not allowed into the guest rooms. Continental breakfast served. Private entrance, off street parking available.

Jul 14 – 21

G$15,137 GYD per night

Home in Crisfield

5.0 out of 5 average rating, 66 reviews

Marshall’s Retreat Chesapeake small town getaway

Modern 3 bedroom home centrally located in the heart of Crisfield, Md. Off & on street parking. Minutes away from our towns new bike trail, boat & Kayak launch, parks, Wellington Beach, shopping, Ferry’s to The Islands, fishing piers, restaurants, Crab & Cruise, 413 crab & concert, beautiful views. about an hour drive to Ocean City, Assateague or Chincoteague. Or stay in & relax watch Cable tv, Wifi. Please be sure to research the area online to make sure it’s right for your needs. Thanks

Jan 9 – 16

G$29,844 GYD per night

Cottage in Westover

4.99 out of 5 average rating, 182 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.

Dec 19 – 26

G$70,387 GYD per night

Home in Crisfield

4.95 out of 5 average rating, 254 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.

Nov 11 – 18

G$33,404 GYD per night

Home in Crisfield

5.0 out of 5 average rating, 17 reviews

Myrtle Manor- Crisfield Maryland

Welcome to our newly renovated Pearl Certified home located in beautiful downtown Crisfield Maryland! Whether you want to explore our small town on the new bike trail, shop the small businesses in town, visit Janes Island State Park, relax on Wellington Beach, take a day trip to Smith Island, or enjoy an evening Sunset Cruise on the bay - the choices are unlimited. Or you may just want to relax and enjoy our home which has cable TV and WIFI.

May 19 – 26

G$31,567 GYD per night

Cottage in Westover

4.92 out of 5 average rating, 142 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!

Oct 4 – 11

G$48,844 GYD per night

Cottage in Saxis

4.87 out of 5 average rating, 204 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

Dec 14 – 21

G$27,912 GYD per night

Villa in Princess Anne

4.83 out of 5 average rating, 120 reviews

Waterfront Retreat & Guest House

Enjoy a relaxing private retreat with an amazing view of the water. Come to stay at the house the whole time enjoying sunsets, kayaking, building sand castles, playing in the water, and making great meals or venture to many nearby towns with great restaurants, hikes, golfing, breweries, bike paths, and more. Enjoy your own private 100 ft pier and sandy beach. **great wifi in main house and guesthouse

Dec 7 – 14

G$169,372 GYD per night

Home in Westover

4.97 out of 5 average rating, 59 reviews

Waterfront Chesapeake Bay Retreat

Welcome to our peaceful sanctuary on the Manokin River. Whether you're looking for a place to unplug and focus on connecting with family and friends, have some time to yourself or need a change of scenery for telework, Manokin House is the ideal retreat. The waterfront location allows you to truly enjoy the natural beauty of the Eastern Shore.

Apr 10 – 17

G$87,734 GYD per night

Guest suite in Deal Island Historic District

4.91 out of 5 average rating, 88 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.

Jan 28 – Feb 4

G$14,316 GYD per night

Cottage in Deal Island Historic District

4.96 out of 5 average rating, 69 reviews

Private Beachfront Cottage with 2 Bedrooms + Loft

Relax and enjoy your own private beach with panoramic views of the Chesapeake Bay! Our cottage is in a quiet strip of Deal Island shoreline, but still boasts high speed internet - so you don't have to completely disconnect while you're here ...unless you want to, of course. We won't tell.

Oct 10 – 17

G$56,964 GYD per night

Home in TYLERTON

4.95 out of 5 average rating, 118 reviews

3 bedroom/2.5 bath Smith Island bungalow with dock

The Quietness of the island and the beautiful scenery around the waters edge. You will hear the birds and the waves and the wind. The island is void of loud noises, mostly nature. The home was built around 1860 and fully restored 2008. its perfectly imperfect!

Sep 13 – 20

G$30,040 GYD per night

Vacation rentals for every style

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Popular amenities for Somerset County kid-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Home in Princess Anne

4.88 out of 5 average rating, 8 reviews

Ole Pirate House

Oct 7 – 14

G$29,370 GYD per night

Home in Deal Island Historic District

5.0 out of 5 average rating, 12 reviews

House of the Setting Sun/Deal Island Bayfront Home

Mar 25 – Apr 1

G$44,511 GYD per night

Home in Deal Island Historic District

5.0 out of 5 average rating, 39 reviews

"Promise Point" Bay front home with dock. 3BR 2BA

Apr 17 – 24

G$60,409 GYD per night

Home in Westover

4.95 out of 5 average rating, 19 reviews

Private beach with comfort

Nov 5 – 12

G$85,559 GYD per night

Home in Oak Hall

4.95 out of 5 average rating, 40 reviews

Converted Railroad Bank - 15 MINS to Chincoteague

Sep 8 – 15

G$32,026 GYD per night

Home in Saxis

4.81 out of 5 average rating, 32 reviews

Beautiful Bayfront with Sanctuary Private Beach

Dec 30 – Jan 6

G$36,669 GYD per night

Home in Westover

5.0 out of 5 average rating, 18 reviews

Sportsman's Cottage

Dec 13 – 20

G$43,450 GYD per night

Home in Deal Island Historic District

5.0 out of 5 average rating, 20 reviews

Deal Island Lodge

Apr 3 – 10

G$51,182 GYD per night

Kid-friendly apartment rentals

Apartment in Crisfield

4.92 out of 5 average rating, 39 reviews

Stylish Condo With A Great View

Aug 15 – 22

G$52,873 GYD per night

Apartment in Crisfield

Waterfront Condo Getaway

Dec 6 – 13

G$54,254 GYD per night

Apartment in Temperanceville

4.5 out of 5 average rating, 46 reviews

Farm house apartment

Jul 3 – 10

G$11,930 GYD per night

Apartment in Crisfield

5.0 out of 5 average rating, 7 reviews

Forever Water Views

Jan 19 – 26

G$50,308 GYD per night

Apartment in Crisfield

Crisfield's Gateway

Aug 13 – 20

G$38,176 GYD per night

Apartment in Crisfield

Cozy Apartment w/ Water Views!

Jul 9 – 16

G$39,548 GYD per night

Apartment in Princess Anne

Home Away From Home (UCL)

Jun 11 – 18

G$34,597 GYD per night

Apartment in Crisfield

New place to stay

Newly renovated 3 Bedroom Condo

Oct 21 – 28

G$51,335 GYD per night

Kid-friendly condo rentals

Condo in Crisfield

4.85 out of 5 average rating, 33 reviews

3 Bedroom Waterfront Condo with Pool and Boat slip

Dec 17 – 24

G$43,370 GYD per night

Condo in Crisfield

4.88 out of 5 average rating, 52 reviews

Crisfield Condo with Spectacular Views

Oct 29 – Nov 5

G$60,072 GYD per night

Condo in Crisfield

4.88 out of 5 average rating, 17 reviews

Beautiful Waterfront Condo w/ Community Pool!

Jun 19 – 26

G$61,281 GYD per night

Condo in Crisfield

5.0 out of 5 average rating, 24 reviews

Breathtaking Waterfront Condo with Boat Slip

Oct 16 – 23

G$68,528 GYD per night

Condo in Crisfield

Direct Chesapeake Bay Waterfront Condo

Feb 16 – 23

G$71,580 GYD per night

Condo in Crisfield

Crisfield Vacation Rental Condo w/ Community Pool!

Nov 30 – Dec 7

G$80,107 GYD per night

Condo in Crisfield

New place to stay

Crisfield Penthouse Retreat Amazing Water Views!

Nov 14 – 21

G$34,299 GYD per night

Destinations to explore