Holiday rentals with a fireplace in Somerset County

Heaven on the Bay - The Perfect Coastal Cottage

This Chesapeake Bayfront cottage has spectacular views to take you away from it all in any season. Watch the sunrise & sunset everyday! It boasts more than 120 feet of waterfront, and you can enjoy time on the 70 ft. dock! Launch kayaks & SUP from the small sandy beach in summer, or cozy up to the wood stove in the winter. You’ll love the quaint cottage feel, modern kitchen & baths, with stunning bay views from every room. Kayaks, SUP, bicycles & crab traps too. Your peaceful retreat awaits!

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.

Countryside Home in Princess Anne

Escape to tranquility at our private home in the serene countryside. Our spacious and comfortable three-bedroom, two-bathroom home provides ample space for families, couples, and groups of friends to relax and enjoy the outdoors. Relax in the cozy living area, cook a meal in the fully equipped kitchen, or enjoy an evening around the campfire. With comfortable bedrooms and a peaceful location, it's the ideal getaway for a relaxing break. Book now and experience the beauty of rural living!

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).

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.

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!

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.

Farmhouse located on a horse farm

Farmhouse located just minutes off of Route 13 in Princess Anne, MD. Enjoy a peaceful farm experience while staying in a charming farmhouse with lots of character. You can walk the grounds of the farm, including a trail through the woods, or take a swim in the pool. We do not offer horseback riding lessons but you can interact with the horses. We are minutes to shopping, groceries, restaurants, UMES, and a short ride to Chincoteague (32 miles) and Ocean City (40 miles).

Year Round Playground - Rare Rustic-Modern Getaway

Enjoy best of Eastern Shore living in this unique property that provides privacy & exciting amenities for everyone: POOL, 7 PERSON HOT TUB, OUTDOOR KITCHEN, REC ROOM, FISHING, w/GOLFING & BEACHES nearby! Newly renovated 3BR/2.5BA offers guests an opportunity to have in-the-woods feelings w/o sacrificing comfort. Escape the city rushes on a rare waterfront property w/private dock on East Creek leading out to the bay! Don’t miss out on Insta-worthy photo ops! BOOK NOW!!!