House holiday rentals in Somerset County

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Top-rated house rentals in Somerset County

Guests agree: these houses are highly rated for location, cleanliness and more.

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Guest favourite

Home in Smith Island

4.93 out of 5 average rating, 14 reviews

HH Ranch on Smith Island w/ Golf Cart

Relax in this 1910 era Smith Island home. Has one large upstairs bedroom with second twin bed separate from main bedroom. Comfortable family room with seating for 5. Updated enclosed patio is ideal in the summer. Large kitchen fully stocked to cook your meals. New front deck. Large bathroom with dual rainhead shower. Easy access to the water. Bikes and SUP available in the shed. Kayaks are covered outside by shed. Island is only accessible by boat. Enjoy the tranquility of this unique place.

Top guest favourite

Home in Smith Island

4.89 out of 5 average rating, 75 reviews

Smith Island Yummy Artist Retreat

I believe in actually having an experience when travelling! Be comfortable while experiencing life thru the eyes of an artist. The house has the flavor of island life. Windows that catch breezes and airy spaces that feel welcoming. I am a resident artist also living both in MD and NJ. I have created my home without limitations! I am continually expanding and developing the spaces to be alive and fun. Ferries leave Crisfield MD at 12:30pm to come to island. Sunday ferries sept-may are iffy!

Guest favourite

Home in Crisfield

4.99 out of 5 average rating, 86 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 from our towns new bike trail, boat & Kayak launch, park play ground,Wellington Beach, shopping, Ferry’s to The Islands, fishing piers, restaurants, Crab & Cruise (within walking distance), 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.

Top guest favourite

Home in Smith Island

5 out of 5 average rating, 21 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

4.85 out of 5 average rating, 27 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 favourite

Home in Princess Anne

4.94 out of 5 average rating, 17 reviews

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.

Guest favourite

Home in Deal Island Historic District

4.94 out of 5 average rating, 32 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!

Top guest favourite

Home in Crisfield

4.96 out of 5 average rating, 288 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.

Top guest favourite

Home in Deal Island Historic District

4.97 out of 5 average rating, 30 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 favourite

Home in Saxis

4.88 out of 5 average rating, 247 reviews

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

Superhost

Home in Westover

4.94 out of 5 average rating, 82 reviews

Beachfront 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.

Superhost

Home in Westover

4.91 out of 5 average rating, 35 reviews

Private beach with comfort

Relax with the whole family at this peaceful place to stay. Fantastic waterfront home.Your own very private location with your own sand beach. Perfect for family get away with water activities, swim,fish,Kayak etc.This home has a Handicap ramp and a Walk in shower with small curb for anyone who needs.