Vacation rentals with outdoor seating in Somerset County

4.92 out of 5 average rating, 51 reviews

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

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).

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.

5 out of 5 average rating, 44 reviews

A red A-frame cottage is set on a green lawn, flanked by tall trees. The building features a spacious wooden deck with a staircase leading to the entrance. Fields stretch out in the background under a cloudy sky.

Cabin in Westover

Chalet Style Home, private country setting

Crooked Elm Cottage, nestled in Somerset County on Maryland's lower Eastern Shore, is ideal for outdoor enthusiasts. With easy access to the Chesapeake Bay and Atlantic Ocean, guests can enjoy birdwatching, hiking, fishing, boating, and biking, making it the ultimate base for adventure. Fully renovated, this charming retreat features a modern kitchen, a spacious living/dining area, high-speed internet, two expansive decks, and an outdoor recreation room complete with a pool table.

5 out of 5 average rating, 3 reviews

A wooden boardwalk extends towards a bayfront home, bordered by tall trees and grassy areas. Numerous posts line the sides of the boardwalk, leading to tranquil water views. Two houses are visible in the background, framed by serene coastal scenery.

Cottage in Westover

Bay Beauty with boat slip & waterfront views!

Marvel at the breathtaking 360 views from every window throughout the house! The wraparound decks and private balconies are the perfect locations to take in the amazing expansive waterfront views in every direction! Stroll the 150’ boardwalk and enjoy the water views leading to a 200’ pier and 20’ x 20’ dock with boat slip for the avid boater. You will see nature all around you. Fish, crab or just relax off the dock while enjoying the spectacular views and most amazing sunsets!

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.

4.86 out of 5 average rating, 139 reviews

A serene beach scene features a wide stretch of golden sand meeting the calm waters under a clear blue sky. The shoreline curves gently in the distance, with sparse vegetation along the edges. Traces of footprints are visible in the sand, suggesting a tranquil area for walking.

Cottage in Saxis

ISLAND BREEZE Near Chincoteague Island

Waterman’s fishing village Surrounded by water on three sides & Virginia Wildlife Refuge on fourth side. Walking distance to beach (located on Dennis Lane) Kayaking & Canoeing Wildlife Fishing Pier Boat Ramp Marina Public Pavilion Ice Cream Shop 1-Restaurant (Capt E’s Hurricane Grill & Tiki Bar) Museum Multiple Seafood Shanty’s (Steamed Crabs Available during season)

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

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.

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.

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House rentals with outdoor seating

4.96 out of 5 average rating, 51 reviews

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.

Home in Crisfield

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.

4.94 out of 5 average rating, 48 reviews

The exterior of a two-story white house is visible, featuring a covered porch and a prominent brick chimney. Lush green grass and well-maintained bushes surround the home, while a large American flag gently flutters at the front, adding a touch of character to the inviting setting.

Home in Quantico

Home in historic village of Whitehaven, Maryland.

SavannahRating, 5 stars2 weeks ago

We had such a great experience staying at White Haven, definitely a beautiful and peaceful retreat!

4.25 out of 5 average rating, 4 reviews

A calm waterway is depicted, flanked by charming white cottages. Lush greenery borders the scene, with a clear blue sky above. The gentle ripples on the water reflect the surrounding structures, illustrating a serene and tranquil island setting.

Home in Smith Island

Blue Anchor Cottage at Smith Island

Morgan McdanielRating, 5 stars21 months ago

We had 4 adults and one young kid staying there, and the space felt very comfortable for all of us. We each had our own space to retreat to, and the communal spaces accommodated all of us comfortably. The kitchen was very well-stocked, the views were beautiful, and the beds were very comfortable. Highly recommend.

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..

5 out of 5 average rating, 6 reviews

The exterior of a modern house is shown, featuring a triangular roof with expansive windows allowing natural light. A wooden deck with railings surrounds the front, providing a welcoming entrance. Nature surrounds the home, enhancing its tranquil setting.

Home in Marion Station

Waterfront with Private Dock, Fire Pit & Hot Tub

LaRating, 5 stars1 month ago

Ms. Meagan was very responsive. The decor was modern and the home is well appointed. Great views all around. Wish we had more time to enjoy the amenities.

5 out of 5 average rating, 16 reviews

A spacious, charming Victorian house stands surrounded by lush green grass and trees. The exterior showcases light blue shutters on white siding, with a welcoming porch featuring hanging plants and rocking chairs. The landscape is well-maintained, enhancing the home's inviting presence.

Home in Fishing Creek

Hoopers Island Victorian with 360 Water Views

ColleenRating, 5 stars2 days ago

Water views, sea breezes and the songs of seabirds-what more could you ask for? If you are like us and enjoy the peace and serenity of nature, this is your haven. Kristin's home made us so happy! The screened porch and open layout of the living room and dining room provided beautiful breezes and views. The house is a perfect blend of modern updates and old architectural charm. The kitchen is well stocked and there is a new deck and outdoor shower that we all loved, especially my daughters after coming back from a run or bike. Additionally, Kristin was an excellent host. She is very thorough in meeting all of your needs. She provides highlights of the area, tips on food and even recipes in her binder. She responds very quickly as well. While the location is remote, it is ideal for people seeking relaxation. We were there for the Ironman and while the drive was somewhat of a distance, it was worth it! We will return! I wanted to stay and just read a book on the porch! Thanks