Smoking friendly holiday rentals in Southern Maryland

Frolic Fields: A Woodsy 14 Acre Homestead w/ Sheep

Easily escape to the woods on a 14 acre homestead that's only 20 miles from DC. Surrounded by the forest with amazing views, designed by artists, this secluded hideaway is a celebration of Nature and Art. Recharge amongst these ancient trees and all the singing critters that soundtrack the night. Enjoy a fire, frolic in the fields, read on a hammock, strum a guitar, and feel the pressure of modern life melt away. Explore the many bucolic trails nearby. Perfect for retreats and workshops.

Rare New Build Home w/Hot Tub, Fire pit, Game Room

*Rare listing* Nestled just outside of Washington DC, this stunning 5BR home offers an escape from the hustle & bustle. Sink into plush sofas as you unwind with a movie night or be greeted by a spacious patio area, complete with a hot tub & grill. Roast marshmallows & share stories with friends & family around the fire pit. In the mood for a city adventure? We’re located in between DC. Whether seeking relaxation, outdoor adventures, this is the perfect place to experience the best of both worlds

RV Parking on Cambridge Creek

Waterview RV parking with 30amp electric and water hook up! No septic hook up. Located in a business parking lot on Maryland Ave, the gateway to Cambridge! Close to downtown! Just 4 blocks from Route 50 and only 2 blocks from the Choptank River! This space is within walking distance to seafood restaurants, shops, public boat ramp, beach, and parks! Close to all local attractions including the Choptank River Lighthouse, Sailwinds Park, Harriett Tubman Underground Railroad and Blackwater Refuge!

Rare DC Main Floor Bed,Bath,Gameroom,3min To Metro

**RARE** Main floor bedroom and bathroom with no step. 3 Min drive from metro. 10 Min from White house. Free Street Parking in front.Welcome to our spacious 5-bedroom,4-bathroom oasis in the heart of Washington DC!The perfect blend of comfort, style, & convenience!Brand new, newly renovated 3500 sq feet of open concept living.This house boasts ample space for family & friends,ensuring a relaxing & enjoyable stay with double living room and chefs kitchen.8 Min drive to Whole foods and Navy Yard.

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.

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.

Herring Bay Getaway Water view | Deale, Maryland

New, cozy, clean & comfortable waterview house is perfect for a relaxing family or couples getaway! Enjoy bay breezes , bird watching, ships & sunrises from your front porch. 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. Always a relaxing getaway. Super Clean ! New Peloton added this year!

Irie Blue: 4/20-Friendly Oasis w/ Patio & Firepit

Welcome to Irie Blue, DC’s premier 4/20-friendly retreat in vibrant Deanwood. Designed for chill vibes, this cozy space features a private entrance, outdoor patio with firepit, grill, and dining area—perfect for unwinding. Inside, enjoy 2 futons, a queen bed, 55-inch TV, and all you need for relaxation. Plus, a small welcome gift to embrace the 4/20 vibes. 😎 Close to Metro, H Street Corridor, and DC’s top attractions. Cannabis smoking allowed indoors!

Blue Crab Bungalow

Our charming bungalow allows you to relax,refresh and truly unwind while taking in views of the bay. ​ Enjoy amazing sunsets, lots of stars, and the water view from the 2nd story deck, private pier, or around the fire pit. Try crabbing or fishing from the pier. No license needed! A small local beach and public boat ramp are less than 5 minutes away. We are about an hour to Ocean City, Chincoteague, and Assateague.