Vacation home rentals near Chesapeake Bay

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

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

Lovely 2-bedroom 1100 sq ft Apt with free parking

You will enjoy easy access to everything in downtown Portsmouth from this centrally located place. You are in a residential area two blocks from the heart of downtown Portsmouth, a half a mile to the Portsmouth Naval Hospital in the Historic Olde Towne district and a Starbucks one block away. The Virginia Beach ocean front is a half hour away by car. This is a historic building on the National Register of Historic Places. It consists of four apartments; one on the second floor is your Airbnb.

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..

Parkside South, Cape Charles

Parkside offers the perfect getaway for families and/or friends! Conveniently located next to Central Park, 2 blocks from the beach and the main street (Mason Ave). In peak summer we have full weeks available (Sun-Sun) or partial (Sun-Thurs). We open corresponding weekends once the Sun-Thurs books. Check our calendar or social media for weekend openings! We recommend a max of 4 adults or 2 adults and 3 (possibly 4) children, depending on their ages. Our family of 5 stays comfortably!

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.

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!

Waterfront 4 bedroom home with marina facilities

Stunning river views from this spacious family home. The quiet, peaceful setting is perfect for taking in nature and wildlife. The open floor plan that spills onto the patio is great for entertaining. Wonderful spot to enjoy boating, crabbing, fishing, kayaking - all the Severn River has to offer. Home features first floor BR and BR w/ shower, upstairs 3 BR and 2 full BR. Award-Winning Busch Gardens, Historic Colonial Triangle (Yorktown / Williamsburg / Jamestown) Nearby.

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.

Beachhouse, Hot Tub / Pool, Walk to beach / Surf

A Secret Spot – 6BR/4BA Family Oasis with Pool, Hot Tub & Game Lounge | 4-Min Walk to Beach **** COMPLETELY RENOVATED SPRING 2026 **** Discover your dream coastal getaway at “A Secret Spot,” a stunningly appointed 6-bedroom, 4-bathroom home tucked into the peaceful north end of Sandbridge Beach. Just 750 feet from the ocean, this spacious home blends laid-back beach charm with resort-style outdoor living and non-stop entertainment for the whole family.

5 bed 5.5 bath w/ heated pool, 5min walk to beach

NEW beach-modern farmhouse in S. Rehoboth built in 2022. Professionally interior designed. Sleeps up to 10, w/ 5 bedrooms, 5.5 bathrooms, en suite bathrooms in all bedrooms, modern kitchen, coffee bar, wet bar, patio w/ pool (pool open May - Oct, heated in spring & fall), outdoor fire table, grill & outdoor seating. Open floor plan with plenty of space to spread out and enjoy your vacation. On the 2nd ocean block, 5-min walk to beach & boardwalk.

Stylish modern 2BR/2BA - Free Garage Parking!

*Fully renovated 2 BR 2 full bath basement apartment - renovated in 2021! *Private access *Extremely close to the restaurants, attractions, and grocery stores of H St *Short walk to Union Station, Amtrak, buses to/from NYC, and metro station. *Stainless Bosch appliances *Wine fridge. *King beds with excellent, comfortable mattresses. *Spacious and comfortable with a lovesac couch *Dining area *Included secure underground garage parking!