Holiday rentals in Sudlersville

Bayfront Oasis Vacation Rental

Waterfront panoramic views with a crabbing dock and boat slip. 4 bedrooms (full/twin bunkbeds, 2 twin beds + full bath, queen bed + full bath, king bed + full bath, and sleeper sofa in living room); up to 14 guests. Additional features include ½ bath, sunroom, living room, kitchen, laundry room (washer/dryer), and gaming room. Outdoor space with dining table, outdoor kitchen, firepit, gazebo, cornhole. Resort amenities; swimming pool, bikes, playground, pickleball, dog park, marina, store.

Dog friendly, Close to outlets, fire pit, Sleeps 6

Tucked away in a quiet neighborhood, this adorable cottage awaits your next peaceful vacation. With 3 beds/2 baths, there’s space to enjoy a relaxing stay for up to 6 guests with cozy blankets and beds as well as beautiful surrounding gardens. We are only 4 miles to the beaches, 1 mile to outlet shopping, and close to amazing restaurants. You may not even want to leave the cottage at all. Pet friendly (1 dog please). NEW FOR 2024: beautiful bathroom updates and NEW comfy mattress in the master!

Cottage by the Bay

Enjoy what lower, slower Delaware has to offer in this cozy cottage near the bay. This gated family-friendly community offers many activities including pool, kayaking, basketball, pickle ball, and crabbing docks, and is close to beaches, shopping, golf, and dining. This will be your home away from home with 3 bedrooms and 3 full baths, a well-equipped kitchen, and laundry room, all season porch, and a relaxing backyard with a fire pit, bar, dining area, and TV!!! 5 minutes from Baywood Greens!

Bowers Beach - pets ok - low cleaning fee

Welcome to Bowers Beach! This house is walking distance to the beach, Bay View Bar/Restaurant/Live Music, JP's Wharf (waterfront restaurant), and The Captains Lady charter boat. Driving distance to DE Turf Sports Complex (12min), Dover (20min), Harrington (23min), and Tanger Outlets/Rehoboth Beach (41min). We welcome couples, solo adventurers, business travelers, families, tournament teams, big groups, and Dogs welcome (NO CATS). However quiet or lively your stay, our location has it all.

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Our tastefully appointed cottages sit on almost an acre of waterfront property. Peaceful and tranquil, yet close to shops and restaurants, this property is perfect for serene getaways and family gatherings. With 2 separate cottages on one property, everyone will enjoy a unique and private space to relax. From peaceful mornings to magical sunsets on the 60-foot pier, this setting will quickly become a family favorite. This area is great for fishing, kayaking and paddle boarding!

Penthouse Place

Experience luxury in this newly renovated top-floor condo. White noise machines, plush pillows and mattresses ensure uninterrupted sleep while the cozy screened-in porch offers serene pond views. Relax in plush seating, enjoy modern amenities, and rest easy in comfortable bedrooms. Conveniently located in the highly sought after Creekwood community, it is near dining and entertainment options, this condo offers the perfect blend of luxury and tranquility for your getaway.

Maplewood - Simply Comfortable, Dog Friendly

Have fun with the whole family at this stylish place in the center of it all. Near the beach, away from the crowds. Local attractions: Sandhill Fields - .5 miles Sports at the Beach - 1 mile Dogfish Head Brewery - 5 miles Lewes Beach -8 Cape May Lewes Ferry Terminal Cape Henlopen State Park Tanger Outlets - 12.4 miles - 13.9 miles And lots of other tax free shopping. Rehoboth Beach Boardwalk - 17.5 miles Dover Downs - 39.1 miles Many other attractions nearby.

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Woodsey Beach House - Beach, Lake, Woods!

Beach? Check Cabin? Check Lake? Check Have it all at our home near the beach, in a beautiful wooded setting with a lake view! Quiet neighborhood makes you feel right at home. Newly renovated with new appliances and furnishings. The house has an upside-down layout, so most of the living spaces, including the kitchen, dining, and living rooms are on the second floor. The home is unique, bright and comfortable.