House holiday rentals in Assateague Island

Premier St Michaels Cottage- In Town Location

The truly special and restored historic Thomas Blades house is centrally located in the Town of St. Michaels on a quiet st. Shops, restaurants, museums and the Town park with its magnificent water views are steps away. It is a 2 bedroom 1.5 bath cottage with a large paneled family room and a large screened porch. Ideal for a small family or two couples, or a romantic getaway for two. Rate varies by day of the week and season. Discounts for stays of a week or more, or for "last minute" bookings.

Central Location- Walk to Dining & Entertainment!

Experience the ultimate in coastal living at this beautifully renovated home, a stone's throw from the Beach road. Seasonal discounts available, this is your perfect getaway destination. The interior features a bright chef's kitchen with granite countertops and a tiled backsplash, an open-concept first floor with a cozy living room, and a convenient half bath. Retire to the second level where 2 bedrooms await, including a primary suite with a private bath and balcony for serene morning views 🌄

Sunny Days

Casual, spacious open floorplan, all on one floor with a huge back sun porch, nice front sun porch and deck. Centrally located, beaches, historic Berlin, and amenity filled community [pools, golf, pickle-ball etc.] Sleeps 8-9; king, queen, full-twin bunk, single. Must be 25 yrs old or prior service military or first responders. Recent price hikes forced us to cut the cable, switch to streaming services, and install TVs in each room. Linens and beach club parking pass available for a fee.

5 BR Townhouse w/ private elevator-Rehoboth Beach

This townhouse features 5 bedrooms and 3.5 bathrooms, elevator, and plenty of parking. Pets are allowed with a fee, and you can access two gyms. We offer complimentary sheets and towels. Community pools are available from Memorial Day through Labor Day. It is located in a gated community five miles from downtown Rehoboth Beach. Rentals booked from Labor Day to Memorial Day are non-refundable if canceled within 30 days of the rental date. The HOA requires a short-term lease agreement.

Chincoteague Island Creekside Cottage

Creekside Cottage delivers all the feels... July 2020 USA Today "Best Coastal small town". Private dock off large back yard for crabbing or catching the sunset, minutes away from the Chesapeake Bay and Historic downtown, 10 minutes to Chincoteague National Wildlife Refuge (Ponys) and the Beach (golf cart friendly). Everyone can hang on the huge sectional in the eve and play board games or catch up. Smart TV, Wifi, Large cooks kitchen (dbl oven), Table extends to 124". Make Memories!

Beautiful Beach House in Rehoboth

Now Available during Summer Season for the first time! Few spots still open: June 2-11; July 6-16; July 26-30; Aug 25-31 Gorgeous modern spacious house in Rehoboth Beach with large open floor plan on quiet street. Five bedrooms/3.5 baths. Walk to town/beach - four blocks from beach right off Rehoboth Ave. Private pool with two levels of decks, grill and table/umbrella on top deck. Big open kitchen/dining/living area, over 3000 square feet of space overall.

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

Spectacular Accommodations! 4 bdr home , grill

The best place to stay in Bethany Beach , De is Bishops Landing in Millville! It’s 4.8 miles from Bethany Beach Boardwalk . This brand new 4 bedroom single family home with 2 master suites won't disappoint!! It has a large living area, kitchen , and dining areas, spacious outdoor deck access to golf within 3 miles , the community has a pool within walking distance of the house , Pickleball courts ! This is a great place to relax , and enjoy !

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.