Holiday rentals with outdoor seating in Somerset County

4.92 out of 5 average rating, 52 reviews

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

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, 3 reviews

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!

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!

4.88 out of 5 average rating, 65 reviews

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, 212 reviews

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

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, 227 reviews

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.

Guest house in Deal Island Historic District

5 out of 5 average rating, 34 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 about an hour to Ocean City, Chincoteague, and Assateague.

4.86 out of 5 average rating, 139 reviews

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)

Guest suite in Deal Island Historic District

4.9 out of 5 average rating, 114 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

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.

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House rentals with outdoor seating

4.94 out of 5 average rating, 82 reviews

Home in Westover

Beachfront Chesapeake Bay Retreat

MarvinRating, 5 stars3 weeks ago

I loved it, very comfortable, nice beach and organized, I recommend it

4.96 out of 5 average rating, 53 reviews

Home in Crisfield

Catch of the Bay

SonyaRating, 5 stars1 week ago

Janell's place was clean, cozy, and exactly as described. Check-in was smooth, and she was quick to respond to any questions. Great location and thoughtful touches throughout. Would definitely stay again!

4.25 out of 5 average rating, 4 reviews

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, 15 reviews

Home in Princess Anne

countryside home in Princess Anne

ChristenRating, 5 stars4 days ago

10 stars – The Best Host & Perfect Stay! This country spot was everything we needed and more! Super clean, incredibly peaceful, and the perfect escape from the noise of everyday life. The best surprise? Not a single mosquito in sight—which is rare for the country! The host was amazing and made the whole experience even better. We even extended our stay because we didn't want to leave. Already planning our next visit. Highly recommend!

5 out of 5 average rating, 7 reviews

Home in Marion Station

Waterfront with Private Dock, Fire Pit & Hot Tub

JenniferRating, 5 stars1 week ago

Absolutely loved this place, so close to everything, we stayed a week and was busy everyday, relaxed in the hot tub at the end of active, beach, boat, kayak and hiking days, watching herons, whooping cranes, turtles, all sorts of Absolutely beautiful nature. The house was perfect, and Megan was within a few moments available for every question we had. The only thing i suggest is bring bug spray, wasnt prepared for the biting flies, but we learned quickly! There weren't some household items in abundance for a weeks stay, so be sure to bring with you, if you were just stopping for a couple of days youll be fine. But none of that takes away from the beauty of location, the house and how accommodating megan is, she delivered wood on a few hours notice, she answered so quickly, we will most definitely return as soon as we can!!

Home in Westover

5 out of 5 average rating, 4 reviews

The Salt Marsh Shanty

ScottRating, 5 stars1 week ago

A very comfortable home in a gorgeous setting. The marsh out back is like a small private nature preserve. I spent lots of time watching the bird life and the changing light, as well as the easy kayaking at the doorstep. No noise save for birdsong, and I saw hummingbirds, bald eagles, and lots in between. The house is new and very clean with a well-stocked kitchen and room to unwind. The hosts are thoughtful and provide equipment/supplies to enjoy the water and related activities.

5 out of 5 average rating, 17 reviews

Home in Fishing Creek

Hoopers Island Victorian with 360 Water Views

ColleenRating, 5 stars2 weeks 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