Holiday rentals in Sharptown

Church Creek Charm (Close to Blackwater!)

Charming Eastern Shore home built in 1900, located in CHURCH CREEK, MD, less than 10-15 mins from Cambridge, Blackwater National Wildlife Refuge & the Harriet Tubman Underground Railroad museum. Ideal spot for cycling, birding, fishing, canoeing, relaxing, or exploring the many cute towns of Maryland's Eastern Shore. Just over an hour from Ocean City & Assateague Nat'l Seashore. Pet-friendly with a fenced backyard. The Eastern Shore is famous for its seafood, history, nature & fresh produce!

Charming Home in a Neighborhood

Our home is well loved and is a great place to spend some quality family time. It is close to the Salisbury Airport (SBY), Salisbury University (SU), Perdue Stadium (Delmarva Shorebirds) and short drives to University of Maryland Eastern Shore (UMES), the beaches in Ocean City MD, Asseteauge Island, Md and some Delaware beaches too. Winterplace Equestrian Park is within 4 miles and Pemberton Historical Park is just across town. Price includes parking in the attached oversized 2 car garage.

The Red Maple Studio minutes from Salisbury!

Red Maple Studio is a private 1‑bedroom studio on a quiet street in historic Delmar, MD. Kylan Barn – 6 min. Venue 54 – 7 min. Downtown Salisbury – 15 min. SU – 20 min. OCMD – 45 min. Sleeps 4 with king bed and full pull‑out couch. Workspace, fast WiFi, kitchenette, private laundry. Safe neighborhood, off‑street parking, well‑lit walkways. Private backyard patio with 6' fence. Stylish, super clean and comfortable. Sorry....no 3rd‑party bookings, pets, parties, indoor smoking or cooking.

Sunset Breezes - quiet waterfront retreat

Enjoy well equipped waterfront home styled after historic lighthouses. Relax in the hammock by the water under the pines; Enjoy smores by the fire pit. Wood included. Free use of 4 kayaks, 2 paddleboards, and a 3 person canoe. Yard games include corn hole, croquet, & bocce. Dine on the deck while enjoying beautiful sunsets. Bring your cameras for local wildlife. NEW Fun & Fitness barn (sauna, golf simulator, free weights, game space and more (completion date of 4/1/2026 or sooner).

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

Forest Grove Retreat

Quaint two bedroom house situated on a large country lot, fire pit, car port. Centrally located between Salisbury and the Beaches... Ocean City and Assateague Island. Distance to Ocean City and Assateague is about 20-30 minutes. The scenic route to Assateague will take you through Berlin, MD. A beautiful town with lots of restaurants and shopping. The second bedroom is off of the main bedroom, has privacy. We have WiFi! Pets Allowed

One of a kind waterfront home with private dock

Beautiful 2 bedroom/1 bathroom waterfront getaway, with full kitchen and bath, loaded with amenities from coffee, cookware, charcoal grill to crabbing, fishing and kayaks. At the end of the day, gather around the backyard or take a walk down the 125+ foot pier for scenic views as the sun sets on the Wicomico River. Less than a 10 minute drive to the Red Roost and Bull Lips Dock Bar or head to Green Hill Country Club for a round of golf.

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.

Stella

Welcome to Stella! She has been lovingly restored by our family and carefully designed by our son who owns JoonMoon Design with his beautiful wife. We are a family who loves to travel and discover places of rest. Stella was designed with that in mind. She is approachable, comfortable and invites you to kick off your shoes and relax. She is walking distance to Salisbury University and close to many restaurants and stores.

Cattail's Branch

Enjoy the lovely setting of this romantic spot in nature. Tiny house sits on Widow Hawkins Branch Creek and backs up to Johnson Wildlife Mtg Area. Great for bird watchers and nature lovers. Enjoy sitting by the fire pit or relaxing on spacious deck overlooking creek. Quiet and peaceful. Fully equipped kitchen, Queen bed, bathroom, pull out queen sofa bed with privacy wall to make 2rd bedroom. Close to beaches and town.

Salisbury Hideaway

Relax in a quiet part of Salisbury in this cozy, newly renovated 2 bedroom, 1.5 bath home. A modern feel welcomes you home after a long day at work, a sports trip, or vacation. Enjoy all new furniture including luxury bedding and smart TVs. Centrally located and close to downtown for shopping and dining at one of the many local restaurants. Only 30 minutes from the beaches of Ocean City & Assateague Island.

Coastal Waterfront 1 Bedroom Cottage

This waterfront cottage is located 2 miles from Historic Downtown Annapolis and the United States Naval Academy, making it easy to plan your visit. It is located right on the South River in a quiet neighborhood. There is a full outdoor seating and patio area with a grill and fire pit. It has a full kitchen, 1 bedroom, washer/dryer and can sleep up to 4 with the pull-out sleeper couch.