Smoking-friendly holiday rentals in Southern Maryland

Come enjoy Summer on Smith Island at the HH Ranch

Relax in this 1910 era Smith Island home. Has one large upstairs bedroom with second twin bed separate from main bedroom. Comfortable family room with seating for 5. Updated enclosed patio is ideal in the summer. Large kitchen fully stocked to cook your meals. New front deck. Large bathroom with dual rainhead shower. Easy access to the water. Bikes and SUP available in the shed. Kayaks are covered outside by shed. Island is only accessible by boat. Enjoy the tranquility of this unique place.

Warm and Spacious Houseboat with free parking

Enjoy the sights and sounds of nature when you stay in this unique place. Experience the beautiful sunrises and sunsets while the gentle waves help embrace your soul. Well-appointed temperature controlled houseboat. WARM in winter!! Stay at a marina in the DC area. Will send address after booking . Location can vary, usually near Nationals baseball stadium (zip 20024). Average time to Reagan Airport is 15 mins by Uber. Nice bar/restraunt just steps away and bicycle rental end of dock.

Bay-“View” Peaceful, Scenic, Enjoy Crabs N Fish

Welcome to our unique water view home by the bay. Everyone here on Hoopers Island is very friendly and like family. Watch the local waterman as they come in with their catch!. Where fresh crabs, soft crabs, fish n oysters are plentiful!!!! All seafood is local and caught that morning right off the boat!! Having a memorable experience is what its all about. Where you can catch your own crabs and fish. Osprey, bald eagles, Heron and wildlife are plentiful!! It’s peaceful, relaxing and scenic!!

Herring Bay Getaway Water view | Deale, Maryland

New, cozy, clean & comfortable water view house is perfect for a relaxing family or couples getaway! Enjoy bay breezes , bird watching, ships & sunrises from your front porch. Beautiful starry nights by the newly custom built firepit & patio! Located in a quaint waterfront neighborhood with community pier, waterfront green space and yes, amazing sunrises! Great for guests on fishing charters, day tripping, SUP, water sports, cycling and play on the Chesapeake Bay. Peloton bike upon request!

Pristine 1BR, king bed, hot tub, close to IAD

Luxurious, private and serene. Central location – 1 mile to the Metro, 8 minutes to IAD and Reston Town Center. Dedicated street parking. Close to multiple shops and restaurants. 2 patios and a side yard. Private use of the spacious hot tub with over-sized towels & luxurious robes. Enormous king-size Sleep Number® bed for exceptional comfort. Chef-worthy kitchen and washer/dryer. Free Netflix, YouTubeTV and Prime; your own thermostat and ultra-fast WiFi. No shared spaces. Built new in 2023.

The Bird's Nest at Holly Bluff-Riverfront. Beach.

This is a spacious apartment above detached garage, with a roomy balcony. The property sits on the Rappahannock River- guests are welcome to use the beach and dock! Property has a private entrance. The bathroom which is located on the first floor. Apartment is up a flight of stairs above the garage. Plenty of parking. EV charger available. We have self check in and the host is extremely flexible.. We welcome all tenants! The Birds Nest is a perfect getaway destination for relaxing and fun.

Charming Rustic Boathouse right on the Water!

Welcome to the Boathouse!! By offering kayaks, swimming, crabbing/fishing opportunity, a beautiful ambiance for drinks and dinner straight on the water and having almost any water adventure right at your fingertips, this glamping (glamour-camping) bungalow on the water is perfect for just about anyone with an adventurous nature-loving spirit! We encourage you to eat what you catch! And even bring your own boat and stay in one of our boat slips! Minutes from Solomons Island by Boat or Car!

Private Getaway at Four Waters

Relax with the whole family at this peaceful place to stay. We are located at the point where four waters meet. Use the private beach for relaxation or use the private pier for fishing. The water is 5-6ft deep at the end of the pier and can be used for fishing or crabbing. There are 6 adult kayaks and 4 kids kayaks on site available for your use. The large back deck also features Adirondack chairs and a hot tub. We also have a charcoal grill with utensils on site. Charcoal is not provided.

Old World Cottage/Fabulous Sunsets/Polite Pets OK

Immaculate cottage with old world detail and large stone patio. Easement to water to enjoy the fantastic Southern Maryland sunsets dipping beyond the Potomac River. Situated in St Mary’s County near Piney Point and St George’s Island. A short walk to Tall Timbers Marina. Boats and polite pets are welcome with prior approval. Central heat & air conditioning, Front-yard fire-pit, Fast Internet, Smart TVs, Cable 2 Plastic Kayaks Fully stocked Kitchen, and bedding Crab net Fish Table

The Haven at King Copsico Comfortable, Clean, Cozy

Take a break and unwind at this peaceful oasis. A comfortable, cozy and clean cottage with beautiful water views of the Potomac from the bedroom and front sliders. Everything you need is here. Just bring your toothbrush, clothes and groceries! You'll love your stay with a dock and water access across the road. This home is located on one of the best rockfish locations on the Potomac called King Copsico. Fishing species including blue crabs, reddrum, flounder, bass, sea trout and more.

Bright, stylish 1 bed Apt Near H St & Capitol Hill

This stylish 1BR apartment on the 2nd floor comes with a full kitchen, new appliances, washer/dryer, and deck. The queen bed has a Nectar mattress and the queen pull-out sofa has a foam topper--air mattress also provided. Spa-like bathroom with walk-in shower, bench, and stained-glass skylight. Backyard includes a BBQ, fire pit, and privacy fence. Walk to Eastern Market and H St NE dining and nightlife. Sleeps 4 comfortably. Please read the "House Rules" if you plan to come with pets.

Kone Oasis- hot tub, pool, theater/game rm.

Have fun and relax! Near every amenity. Huge Pool w/multiple cabanas, hot tub, trampoline, playground, axe throwing, pool/ice hockey table, arcade,huge theater room, basketball court, grill, spa/library with sauna and full gym!! 5 comfy beds. Rooms split for privacy. Open kitchen/dining/living room. Cold DeerPark water fountain. Now offering RV for additional cost to add additonal sleeping space. Basement apt so there is some movement noise. 20 mins to DC & National Harbor