Vacation rentals in Somerset County

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Top-rated vacation rentals in Somerset County

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Top guest favorite

The exterior of a cottage is depicted, featuring a ramped entrance and a spacious front porch. Two adirondack chairs are positioned on the lawn, surrounded by neatly trimmed grass and colorful flower beds. Tall trees provide partial shade, enhancing the welcoming atmosphere.

Home in Smith Island

5 out of 5 average rating, 26 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!

Guest favorite

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

4.94 out of 5 average rating, 33 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 favorite

A welcoming living area features a cozy seating arrangement with a dark green sofa and two light-colored armchairs. A wooden coffee table sits in the center, adorned with a plant and books. Natural light enters through two windows, accentuating the decorative fireplace and neutral decor.

Cottage in Westover

4.93 out of 5 average rating, 59 reviews

Mary’s Cottage•at Old Beauchamp Homestead•

This quiet, charming, historic property is one of a kind! You won’t want to miss the opportunity to stay here! Mary’s Cottage is the perfect place to enjoy nature and its peaceful atmosphere. You simply won’t want to leave! A 30 minute drive to Chesapeake Bay and about 45 minutes to Chincoteague Island There is plenty of parking space to bring your boat! If you’re traveling with a group we can accommodate more guests in the adjoining “Martha's Cottage” (check my profile for listing).

Guest favorite

A wooden deck is shown with a round table and four black mesh chairs, facing the calm waters of the Wicomico River. Lush greenery surrounds the area, with a dock visible in the background. The sky features soft clouds, enhancing the serene atmosphere.

Cottage in Princess Anne

4.97 out of 5 average rating, 29 reviews

Waterfront Cottage in Mt. Vernon

Relax with the whole family at this peaceful place to stay. Whether getting away for a weekend or visiting near by family there is enough room for all. With a large deck space facing the Wicomico River, you can enjoy outside time with family while each of you has something to do. There is a queen bed, queen pull out couch, and twin to king trundle bed sleeping six! Each stay inlcudes free wifi and parking, kitchen with full amenities, grill, beach, dock use, fishing and more!

Guest favorite

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

4.99 out of 5 average rating, 237 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

LAST MINUTE OPENING-09-27 to 10-03-25 !!!! 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.

Superhost

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.

Home in Crisfield

4.96 out of 5 average rating, 300 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 favorite

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.

Guesthouse in Deal Island Historic District

4.98 out of 5 average rating, 44 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 for swimming and public boat ramp are less than 5 minutes away. We are a little over an hour to Ocean City, Chincoteague, Assateague, and Blackwater Refuge.

Guest favorite

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

4.77 out of 5 average rating, 235 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

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.

Home in Deal Island Historic District

4.95 out of 5 average rating, 38 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!

Superhost

Tall grasses sway gently in the foreground, framing a serene body of water. The calm surface reflects a clear blue sky, while a distant shoreline is visible along the horizon. The scene captures a tranquil natural setting by the water's edge.

Cottage in Saxis

4.86 out of 5 average rating, 222 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

Top guest favorite

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

5 out of 5 average rating, 98 reviews

Big Cozy Loft Overlooking the Farm and River

Located above the apiary workshop, the Loft is a spacious kind suite with a walk-in bath featuring a rainforest shower. Windows overlook the donkey pasture, river, farm, and gardens, Each morning, a farm-fresh breakfast is delivered. The Loft includes a small refrigerator plus coffee and tea essentials. Designed for a true retreat, there is no WiFi, TV, or smoking. Please note: children are not permitted.

Guest favorite

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.

Guest suite in Deal Island Historic District

4.87 out of 5 average rating, 123 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.