Vacation rentals in Dagsboro

The Red Barn Suite

Stay at our brand new barn suite located on our family farm and enjoy a peaceful and quiet country setting. Come back after the beach (just 8 miles away) and cook on the grill and relax on the private deck overlooking the bamboo and pond. Plenty of room inside with a large living room/ full kitchen, bedroom, and bathroom with a custom tile shower. Our modern and cozy barn suite is just minutes away from Bayside Resort, Restaurants, Assowoman Wildlife Refuge, and Delaware and Maryland Beaches.

Central Haven with Great Fenced Yard

You will be close to everything when you stay in this centrally-located home. The rear deck and grill are great for enjoying time outside. There's a fenced rear yard, making this home a perfect choice for man's best friend. We welcome dogs of any breed, size, and weight. We do offer size-specific pet amenities, so please share a photo of your dog when booking, or provide a basic description so we can set out appropriate amenities. For those traveling with cats, please inquire before booking.

Bella Beach Hill

Come make some memories at Bella Beach Hill. Thoughtfully designed and well stocked with amenities. Perfect for families, fishing trips, golf getaways, or just plain old beach fun. Plenty of room for parking and outdoor space. Includes private master with on suite bathroom and separate entrance. Linens provided, washer, dryer. Fully stocked kitchen with cooking utensils. Private separate entrance for master bedroom with on suite. Working flower farm with honor system cart. Relax and enjoy!

Coastal Castaway

Cozy and completely remodeled, this charming two-bedroom, one-bath apartment is the perfect beach getaway! Comfortably sleeping up to six with a pull-out couch in the living room, this home offers plenty of parking for your watercraft. Enjoy the screened porch with a table & chairs to relax. After a day at the beach just 15 miles away refresh in the convenient outdoor shower. With a public boat ramp 2.8 miles away and the Indian River just steps away! Pack your bags and get ready to unwind!

Edgewater Escape - Luxury Bayfront Loft with Porch

You've never seen waterfront like this. Welcome to Edgewater Escape, a luxury bayfront loft apartment that hangs entirely over the bay on 7th street in downtown Ocean City. Sit on the bay front porch or hang out inside and watch boats, dolphin, birds, and sometimes even seals swim by within feet of the porch. The loft has a roomy king sized bed and the downstairs couch pulls out into a comfy queen bed. Recently renovated, it comes fully equipped for your big trip or quiet staycation :)

The Garden at Clayton House

This newly renovated home in the heart of Dagsboro is a peaceful garden getaway. Visitors are perfectly situated to enjoy the world-class Delaware Botanic Gardens and are minutes to Millville, Ocean View and the DE & MD beaches. From Clayton house you can walk to charming antique & gift shops, a diner style restaurant, a cafe with coffee and ice cream, a toy store, a quilt shop, a barber shop and beauty parlor, a movie theater and a beautiful park. Come experience the charm of Dagsboro.

Lighthouse Cottage- Pet Friendly & Close to beach

Best deal in the area only 9 miles from Ocean City, MD and Fenwick Island, DE Quiet and away from the noise and traffic at the resorts. Room for your Boat or motorcycle trailers. Close to boat ramps. Close to historic townships. Selbyville DE, Berlin MD, Snow Hill Md and more. Visit Ocean City beaches and boardwalk or maybe you want to explore Bethany beach or Rehoboth beach. Relax with the whole family at this peaceful place to stay. Priced so you don't stray from your budget.

Tiny Cottage at Good Earth, near Bethany Beach

Welcome to the "Tiny Thyme Cottage" at Good Earth. The cottage is super cozy, perfect for a couple, with 1 queen bed, a kitchen & bathroom, and a small living area. You'll be staying on our 10-acre property, 4.7 miles from Bethany Beach. Convenient amenities include 2 on-site restaurants, market, theater, and ample parking. Our AIRBNB "Village" includes 2 tiny houses, a lofted apartment, and 2 cottages on the property. Staying at Good Earth is more than just a beach trip!

Delightful Skoolie Near Bethany Beach

Try tiny living! Come to the Delaware beach for a unique glamping experience. The Coastal Cruiser is a 1985 Thomas School Bus turned tiny home. Spend your days exploring the Delaware Coast and come home to a rustic Skoolie with a full kitchen & outdoor area. You have access to fire pit, grill, and outdoor seating area. We’ve renovated- there is a bunk bed, and a full bathroom with toilet, shower, and sink. The bathroom is in a separate building about 20 ft from the bus.

Hobbs & Rose | A Peaceful Cottage Escape

Built in 1941 from historic “clinker bricks,” this restored cottage is a dreamy place to slow down and reconnect. Surrounded by enchanted gardens and close to the beach, Hobbs & Rose is filled with charm—gorgeous living spaces, a carved marble soaking tub, and thoughtful details throughout. Enjoy a romantic getaway and unwind in our Sanctuary meditation room, where birdsong and forest friends welcome you. You relax—we’ve created every detail to help you feel restored.

Mi Casa Su Casa

Enjoy this beautiful family home with family and friends located in the small quiet "Town of Frankford". The location of the house is very central to many places, such as beaches, state parks, restaurants, local farms, cafes, etc. Nearby towns and beaches such as Bethany Beach (18 minute drive), The Indian River Inlet (20 Minute drive), Dewey Beach, Rehoboth Beach, Fenwick Island, Ocean City (25 minute drive) and more... Nearest airport SBY - 35 minute drive.

Secluded Waterfront - Beach 15mi, Kayaks, Firepit

Casa Blue Heron is a 2,254 ft² (209 m²) custom waterfront home with a private dock, firepit, and water views throughout - nestled on a tidal inlet connected to Chincoteague Bay - and near Assateague, Berlin, Ocean City, Snow Hill, and much more. ★ "A private and tranquil setting where it is impossible not to relax and appreciate nature… Wish I had booked an extra day!" Add us to your wish list by clicking the ❤️ in the upper-right corner.