Kid-friendly vacation rentals in Somerset County

4.93 out of 5 average rating, 14 reviews

A modern kitchen features a central island with a bright countertop and a small plant centerpiece. Stainless steel appliances line the walls, complemented by light-colored cabinetry. Natural light enters through sliding glass doors, while stylish pendant lights hang above the island.

Home in Princess Anne

Peaceful Home Away from Home

Take a break and unwind at this peaceful home...or take advantage of the convenience to outdoor Eastern Shore activities. Conveniently close to crabbing, boating and fishing, this home provides peace and quiet while steps away from the joys of country living. Whether you're in town for the Skipjack Races in Deal Island, MD or graduation at HBCU, UMES, we are close enough to "town" but yet far enough from the hustle and bustle of town living. Travel Healthcare Professionals are welcome.

5 out of 5 average rating, 85 reviews

An outdoor seating area is set by the water, featuring two Adirondack chairs facing a fire pit. A tranquil sunset casts a warm glow over the lake, while the surrounding landscape includes trees and soft grass. The scene promotes a peaceful atmosphere.

Farm stay in Westover

Big Cozy Loft Overlooking the Farm and River

The Loft is located above the apiary workshop. It is an expansive king room with bath. Walk-in shower has a rainforest head. Views of the donkey pasture out your window! From one side you have a view of the farm & river, the other apiary, gardens & river. The loft is the perfect place to cozy up. Each morning you will have a farm fresh breakfast. The loft has a small refrigerator, tea, coffee with all your necessities. No WiFi/TV or smoking on property. No children in Loft.

A charming single-story home is highlighted by a welcoming entrance with a wooden porch, featuring steps leading to the front door. The neatly landscaped yard contains a small flowering tree, while large windows provide natural light. An American flag is displayed proudly on the exterior.

4.96 out of 5 average rating, 286 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.

4.88 out of 5 average rating, 65 reviews

A cozy seating area featuring a plush sofa and a comfortable rocking chair. A small lamp provides soft lighting beside the large window, which frames views of the surrounding fields. A decorative rug anchors the space, enhancing the inviting atmosphere.

Guest suite in Westover

The Hideaway Suite

Welcome to our humble farmhouse guest suite, your own little slice of tranquility nestled amongst the fields and forests. Tucked away from the hustle and bustle, our home is your perfect getaway, providing peace and quiet while still being conveniently close to Route 13. Once you step inside to the comfort of your suite on the second floor, you're in for a treat with beautiful views and idyllic sunsets. We look forward to hosting you in our lovely farmhouse.

4.75 out of 5 average rating, 209 reviews

The exterior of a two-story house is shown, featuring a light-colored façade and multiple windows. A staircase leads to an entrance at the front. A well-maintained lawn surrounds the structure, and a friendly corgi is visible on the grass.

Guest suite in Crisfield

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.

Home in Deal Island Historic District

The two-story farmhouse is surrounded by a spacious yard, highlighted by a prominent American flag flying in front. Large windows allow natural light, while the earthy green exterior blends with the surrounding trees. A charming white bench adds to the inviting outdoor space.

4.97 out of 5 average rating, 29 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!

4.99 out of 5 average rating, 226 reviews

An aerial view highlights Rumbley Cottage's proximity to the shoreline and wetlands. The landscape features a mix of sandy beach, shallow waters, and expansive marshlands under a clear blue sky, offering a serene setting with natural beauty and tranquility.

Cottage in Westover

Rumbley Cottage on the Tangier Sound-Private Beach

Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at 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 Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

Guesthouse in Deal Island Historic District

A vibrant sunset casts a warm glow over the water, blending hues of orange, purple, and pink. Silhouetted pilings rise from the bay, while gentle waves reflect the colorful sky. A small dock is visible in the foreground, inviting guests to enjoy the serene view.

5 out of 5 average rating, 33 reviews

Blue Crab Bungalow

Our charming bungalow allows you to relax,refresh and truly unwind while taking in views of the bay. Enjoy amazing sunsets, lots of stars, and the water view from the 2nd story 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.

4.88 out of 5 average rating, 247 reviews

A compact kitchen area is highlighted by a wooden breakfast bar with two high-backed stools. A coffee maker and dining settings are present, while white cabinets and modern appliances complement the space. Art pieces decorate the walls, adding a touch of character.

Home in Saxis

ISLAND RELAXATION Near Chincoteague Island

2 Story home build in early 1900's Near Chincoteague Island, Virginia Waterman's fishing village, surrounded by water on three sides & Virginia Wildlife Refuge on fourth side. 400ft. Walking Distance to Beach, Kayaking & Canoeing, Wildlife, Fishing Pier, Boat Ramp, Marina, Public Pavilion, Ice Cream Shop, 2 Restaurants, Museum, Multiple Seafood Shantys

Guest suite in Deal Island Historic District

The exterior of the suite features a light-colored siding with brown shutters on either side of the door. A sturdy ramp and steps provide accessible entry. A small porch is visible in front, and the bright blue sky serves as a backdrop.

4.9 out of 5 average rating, 113 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.

Cottage in Deal Island Historic District

A wooden boardwalk leads to a charming beach cottage, flanked by sandy beach and lush greenery. The cottage features large front steps, a light-colored exterior, and multiple windows offering views of the surroundings. The peaceful shoreline setting enhances the inviting entrance.

4.95 out of 5 average rating, 85 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.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Somerset County kid-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Kid-friendly house rentals

4.95 out of 5 average rating, 80 reviews

The image captures a vibrant sunset over the water, featuring colorful clouds and a serene horizon. Tall grasses border the foreground, enhancing the natural beauty of the waterfront location. Soft rays of light emerge from the clouds, creating a peaceful atmosphere.

Home in Westover

Beachfront Chesapeake Bay Retreat

SarahRating, 5 stars2 weeks ago

Fantastic airbnb experience! The house is cozy and comfortable, fits a lot of people, and has so many amenities. You can have a peaceful time without going stir crazy and I didn't have any concerns about anything while there because of the great hosts! Will be back the next time I find myself in the area!

The exterior of a modern, single-story house features a light blue façade with contrasting dark shingles. A wooden staircase leads to the front door, while a small deck is visible to the left. A paved walkway runs along the well-maintained lawn.

4.99 out of 5 average rating, 86 reviews

Marshall’s Retreat Chesapeake small town getaway

WillettaRating, 5 stars3 months ago

I am originally from the area and I come here occasionally. I usually stay about 45 minutes from Crisfield. This Home had everything that we needed. I always bring a special bag with cleaning supplies, toiletries, hand soap, etc. But this place has it all. I love the wall decorations and am going to use some of those for ideas for our home. Thank you for the use of your home. It was very affordable. We will definitely book again.

A light-colored couch with striped black and white pillows is positioned in a spacious living area. A round, dark wood coffee table sits in front of the couch, accompanied by a soft area rug. Natural light enters through two nearby windows, illuminating the room.

4.96 out of 5 average rating, 51 reviews

Catch of the Bay

BrandonRating, 5 stars1 month ago

Felt like I was home even being away, love the town of Crisfield and this place made us feel safe and secure as well as very Comfortable. We will be back for another short stay again before summer ends.

4.84 out of 5 average rating, 81 reviews

A wooden dock extends into the water, leading towards a vibrant sunset where the sun is partially visible above the horizon. The sky is painted in hues of orange, pink, and purple, while the calm water reflects the colors, creating a tranquil scene.

Home in Smith Island

Smith Island Spectacular Sunsets!

KathleenRating, 5 stars2 weeks ago

We absolutely loved our stay on Smith Island. Gretchen was super helpful with advice and everyone was so nice! We are already talking about going again someday soon.

4.93 out of 5 average rating, 14 reviews

A cozy living area is furnished with soft gray seating, including two recliners and a spacious sofa. A wooden coffee table centers the room, complemented by a patterned rug. Light filters in through large windows, enhancing the inviting atmosphere, while wall art adds a touch of nature.

Home in Princess Anne

countryside home in Princess Anne

AlexisRating, 5 stars3 days ago

Katlynn was a phenomenal host, she was quickly responsive whenever I had a question and was super flexible with me and my stay. If you’re looking for something peaceful and to feel right on at home, this is the place to go.

Home in Deal Island Historic District

A dock extends over calm waters, framed by a vibrant sunset showcasing hues of orange and purple. A picnic table is positioned on the dock, and a flag gently flutters nearby, enhancing the peaceful scene.

4.94 out of 5 average rating, 32 reviews

House of the Setting Sun/Deal Island Bayfront Home

DawnRating, 5 stars1 week ago

Once again, our family had an awesome stay in this beautiful home. Definitely will be back..

A charming two-story cottage features a traditional white exterior with black shutters framing multiple windows. A welcoming front porch is accessed by a brick pathway, while a mailbox stands at the edge of the neatly maintained lawn. Stately trees provide a backdrop.

4.86 out of 5 average rating, 22 reviews

Cozy Crisfield Cottage

LenaRating, 5 stars3 days ago

Jackie’s place was perfect- so much space, impeccably clean, stoked with everything we needed, and close to everything we needed! Jackie was so quick to respond to all messages! If we’re ever back in Crisfield, hope to stay here again!