Holiday rentals with breakfast in Southern Maryland

Beautiful and spacious 3 bedroom

Beautifully decorated and spacious home in a charming, Alexandria neighborhood near the King Street metro and the shops and restaurants of Old Town. Just a 16 minute drive to downtown Washington DC, with a chef's kitchen and a relaxing great room. The house is also just a 10 minute drive to the new MGM Casino or the Gaylord Resort and Convention Center at National Harbor. The "no parties in house" rule is strictly followed. If you want to have a party or an event, this is not the place for you.

Family · Location · Walkability

Alice’s DelRay Cottage-Elegant/EV enabled Retreat

This is a beautiful 1938 cottage with gardens on all 4 sides of the property for drinks w/ Friends or grilling with Family. There are multiple skylight sources of natural light. The office space will support any collaboration requirement. Relax in the gardens while your car is plugged into the ChargePoint EV Charger. This is a very comfortable house for any season or length of stay. The house, patios and gardens make an excellent gathering spot for friends and associates to reconnect and relax.

Location · Family · Checkout

The Heart of Del Ray

Enjoy the best of old and new! Separate apartment in a fully renovated 1920 American Foursquare located in the eclectic Del Ray neighborhood of Alexandria, Virginia, where "Main Street Still Exists." A top-to-bottom renovation provides guests with luxury accommodations in a sparkling clean lower level suite with separate entrance. With free street parking, perfect for business or vacation, guests can easily walk to Mount Vernon Avenue's restaurants, shops, coffee houses, bars and galleries.

Value · Family · Wifi

Secluded Waterfront:Kayaks, Sunrises & Unwind

This is a place you come when you need space: real space, quiet, and room to breathe. Set on 18 private acres along the Chesapeake Bay, our Ridge retreat offers a rare kind of calm: uninterrupted nature, open water views, and the feeling of being completely removed from noise, crowds, and schedules-- just land, water, sky, and time. Days unfold slowly with kayaking, crabbing, exploring the land. Evenings end by the fire under dark skies. This is not a tourist destination—it’s a true reset.

Family · Location · Kitchen

Smallwood St Pk, DC, Blackstone, Grill, Parking

Start your mornings right—step into the kitchen through your private entrance and sip coffee as you watch the sunrise from the covered porch. This spacious home comfortably sleeps groups with 4 bedrooms and 10 twin beds, ideal for large families, fishing trips, or retreats. Enjoy the cozy working fireplace, full bathroom, and in-home laundry for added convenience during your stay. 🎣 Bass fishermen welcome—there’s plenty of room to bring your gear and unwind after a great day on the water.

Location · Long stay · Air conditioning

Riverfront Chalet Kayak/Canoe, pier, breakfast!

This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is Solomon’s island. This is a safe space for all🥰

Value · Location · Grill

Peaceful Farmhouse Retreat in Colonial Beach

Winterbury Farm, located in Colonial Beach, is a beautiful secluded house built in the 1800's on 5 acres. Here you will find chickens roaming, a lovely garden and peaceful views. The Farm is the perfect location; just a short 10 minute drive to the golf-cart friendly town of Colonial Beach and less than 20 minutes to Dahlgren. We have beautiful state parks nearby as well as lovely wineries. The house is divided up like a duplex with the hosts living on site but it is very private.

Family · Value · Back garden

Designer Owned Coastal Getaway Loft

Enjoy our private Loft apartment with exclusive beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home. You have a private entrance, so come and go as you please! Note: We are a peanut-free and smoke free property. RELAX in our chic, private loft just minutes from Chesapeake beaches and 10 minutes from Solomons Island & Calvert Cliffs. You will have private access to our amazing beach-- just a 5 minute drive away. Please let us know if you plan to use it!

Value · Family · Parking

Luxury Darlington Villa - Near Washington DC

Darlington Villa presented by JB Relaxing Villas takes pride in amazing experiences. After a great tour in DC, or exploring the wonderful nature in VA, head back to your modern villa for relaxation. Not ready to call it a night? Step out and enjoy the lit up private oasis patio deck. Look at the stars with a cozy throw and create unforgettable memories. The next morning go for a nature walk at the boardwalk or drive out to Historic Occoquan for a delightful brunch.

Value · Location · Wifi

Breton Bay Guesthouse ~ ~ No cleaning fee

Located in the preferred Breton Bay Golf & Country Club neighborhood, this immaculate guesthouse is a 900 square foot detached dwelling with fully equipped kitchen, living room, separate large bedroom, bathroom with shower, washer and dryer, and balcony. Will consider setting up the space to accommodate your child and/or infant/toddler. Plenty of parking -- enough room for your personal watercraft or small boat!

Family · Location · Check-in

Lovely Lower Level 2 Bedroom Suite - Dog Friendly

This cozy 2-bedroom basement apartment, featuring queen beds, is centrally located in King George—just 30 mins to Fredericksburg, 15 mins to Colonial Beach, and a short drive to Dahlgren. Off Rt. 301, it's ideal for both short and extended stays. It has a private entrance, outdoor area with a fire pit and gas grill. Dogs are welcome with a small cleaning fee (see details).

Family · Location · Hospitality

Modern 2BR Home | Near DC & Old Town

Modern 2BR, 1.5BA townhouse in Alexandria with pool access, minutes from Old Town, DC, and National Harbor. Stylish open living space, fully equipped kitchen, and cozy bedrooms. Perfect for families, couples, or business trips. Enjoy nearby dining, shopping, and historic sights. Easy access to I-395 and Reagan Airport. Your ideal Northern Virginia getaway!

Location · Family · Comfort