Vacation home rentals in Delmarva Peninsula

Berlin Beach House, near Ocean City & Assateague!

Close to everything when you stay at this newly renovated vacation home in historic Berlin. Big yard, lots of parking, & walking distance to downtown Berlins restaurants, breweries, grocery, & more. 10 minutes to the beaches of Ocean City Maryland or Assateague Island wild horses. Arcade games and bikes added for 2025 season. Above ground pool open Mid May - Mid Sept. 2 washer & dryers. Locally owned managed and cleaned for a worry free stay. All linens and bath towels provided.License#2023-3

Location · Family · Bathroom

Down By The Bay - Cape Charles -1st Floor Primary

🏖Come visit this updated 1930's bungalow. 5 blks to restaurants, shops & beach end of our street 🏠 1st floor Primary KING 2026, w/ large bunky upstairs sleeps up to 8 (+ pack and play & air mattress) 🛶 Take stroll/ride to the beach, hose off in outdoor shower, grill on patio & cozy up to a fire. Or relax in the clawfoot tub! 💻 Work remote? Work space ready for you! Wifi/Netflix. Updated kitchen & laundry space in your home away from home! 🐶 Dogs <50lbs (2 max) ☀️ Sunday-Sunday June - August

Location · Value · Sleep quality

The Observatory on Rose Manor

The Observatory on Rose Manor is a private home. It’s 2 blocks from the heart of downtown & beach. Colonial Beach is the golf cart capital of Virginia, we all drive them here. Rent one when your in town. Just over an hour south of DC. This small town takes you back in time with events & local charm. This brand new rental is on the grounds of Rose Manor. Rose Manor was built 1896 it operated as the New Willard hotel for over 50 years. Come relax on its huge porches & enjoy the water view.

Family · Value · Laundry

Designer apt with high end finishes and furnishing

Located in a large, historic townhouse in the Historic District near Lincoln Park and the Eastern Market this professionally decorated English basement apartment includes original artwork; designer furnishings chosen for comfort; and an open concept living/dining/kitchen accented by a rustic antique dining table that seats up to 6. Lush front garden with cafe' table and seating for 6. The new bathroom features double sinks, lighted medicine cabinets and an extra-large shower. Parking permit..

Location · Family · Biking

Lovely Rear 2 BR Cottage!~ Pets Considered *POOL*

You'll be close to everything when you stay at this centrally-located, completely remodeled 2 unit property in beautiful Stone Harbor. Close to the beach, this 2 bedroom has a POOL (May-September) & a washer/dryer. Primary has a King sized bed, 2nd BR has 2 single beds, sofa has a Queen sleeper. YOU WILL NEED TO BRING SHEETS & TOWELS. No smoking. Check-in at 1pm, check out at 10am. Pets considered on a case by case basis, additional fees will apply. Summer Season runs Memorial Day to Sept 26.

Location · Family · Quiet

Waterfront Home in Ventnor

LIFE IS BETTER ON THE BAY! This 5 bedroom, 3 full bath home is beautifully decorated and sits on the intercoastal canal in Ventnor, just a 3 block walk to the Beach. Swim, paddleboard or kayak right off the dock. Catch beautiful sunsets from the rooftop deck. ** GUESTS MUST BE OVER 30YRS OLD AND HAVE ALL POSITIVE REVIEWS TO BOOK THIS HOME! A GOV'T ISSUED PHOTO ID IS REQUIRED TO BE SENT TO THE HOST WITHIN 24HRS OF BOOKING. The Guest booking the home, must stay at the home. ** NO PETS

Location · Family · Accuracy

5BR | Heated Pool, Hot Tub, Elevator, Game Room

☀️ Welcome to your spacious 4,900 sqft coastal home, just 750 ft from the sand! Thoughtfully designed for gathering & relaxation, this 5-bedroom, 4.5-bath retreat offers the perfect blend of fun and comfort, featuring a heated pool, hot tub, cabana with bar, private elevator, and a game room with arcade games the whole family will love. Enjoy seamless indoor–outdoor living with multiple lounge areas, a fully equipped kitchen, and everything you need for an effortless beach getaway.

Value · Family · Access

Serene Cozy Couples Getaway

Forget your worries in this lovely private getaway that's close to numerous attractions: The upstairs apartment is comfortable with all the amenities needed to make your stay relaxing and enjoyable. We're close to beaches, dining, shopping, and outdoor activities. The charming deck is the perfect spot to relax and enjoy reading a book, having breakfast, dinner, or a nice evening drink. Not suitable for children, pets, Not handicap accessible. No one under 20. No Smoking on premises.

Value · Location · Biking

Waterfront 5 Bedroom Home Close to Annapolis

Beautiful waterfront 5 bedroom home located off of the Magothy River. Close proximity to many shops & restaurants, downtown Annapolis, the Naval Academy & a short drive from BWI. This home was recently renovated and offers a lot of room to host a weekend away with your family or friends. Enjoy the beautiful sunsets from the private pier and almost 1 acre of land. Feel free to use the kayaks, canoes, & stand up paddleboards to explore the breathtaking views of the Magothy River!

Family · Location · Kitchen

Vacay Stay-2BR/1Bath, Family Groups Only

Family friendly upstairs, garage apartment. Located on the same property as Dolores by the Sea, only 0.2 miles away from beach and boardwalk. Nestled in a quiet part of town but close to everything. This quaint apartment is perfect for small family’s looking for a relaxing beach vacation. Due to neighborhood restrictions we can only rent to family groups or individuals 25 y/o and over. This is a upstairs unit and may not be for those who have mobility restrictions.

Family · Location · Indoor spaces

Luxury, Ocean Block 4B/3B Condo at Van Dyke Villas

Come stay at our stunning 4 bedroom, 3 full bathroom, ocean block condo with direct ocean views. This rental has every convenience for the perfect vacation. Located on the same block as the beach, you can have your feet in the warm sand within minutes. Newly renovated, this rental features modern amenities, including a fully upgraded kitchen and bathrooms, a gas fireplace, smart TVs throughout and an amazing, oversized screened-in porch with Ocean views.

Location · Family · Long stay

Mid century vacation condo newly renovated.

Enjoy a stylish experience at this centrally-located place. Expansive ocean views, fully renovated space with tasteful details and a serene palette to maximize your well deserved peaceful vacation time. Walk distance to a great variety of high-end restaurants and beach treasures, gift shops, ice cream parlor and games next door. The unit includes a free parking spot in the building. Enjoy brand new bedding and mattresses and everything else.

Value · Family · Amenities