Smoking friendly vacation rentals in 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.

Margaret's Downtown Vintage Flat-With Parking

Margaret's light-filled first floor Flat has been lovingly restored to maintain 1823 architectural features alongside modern updates. This is a shotgun style flat: please see layout drawing in photos. Think original woodwork, hand painted plaster designs, hardwood & marble floors, cook's kitchen, 'back stairs to nowhere', and a sleeping alcove under the front stairs. Please be prepared for an authentic 1800s experience: the original steam radiators are cozy but sometimes hiss and bang.

Awesome studio tucked away & Centrally located !

Bayview is very close to Greektown, Little Italy, Fells Point and Canton. Each of these commercial developments are no more than 1-2 miles from Drew Street. Restaurants, the waterfront and shopping districts are all located in each of these developments and provide a wide array of tastes and treats. Therefore, if you are a foodie, like wine/beer, antique shops or like to hear a band or singer every once in a while, you can definitely find something to do and travel via Uber, Lyft or Taxi.

Wineberry at Evensong Farm

Camp under the stars at one of our private, outfitted campsites! Our canvas wall tent is all set up and ready for you to come and get away from it all. Drive right up to your site and enjoy the seclusion of 60 acres almost to yourself, with walking paths, creek access, and a campsite to make memories at. Whether you're looking perfect spot for a solo or couple's getaway, or a place for a family gathering, we would love to host you at Evensong Farm! Five star host of campers since 2021!

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 for swimming and public boat ramp are less than 5 minutes away. We are a little over an hour to Ocean City, Chincoteague, Assateague, and Blackwater Refuge.

Sauna, hot tub, great outdoor space!

Escape to our serene suburban retreat in Silver Spring, Maryland, where this 3-bedroom, 2-bathroom home awaits you on a fenced half-acre lot. Immerse yourself in comfort and luxury with amenities such as a private hot tub, sauna, gas fire pit and the expansive outdoor space. Pet friendly w/non-refundable pet deposit. No more than 6 guests at any time, no parties. Please include a list of all guests, per Montgomery county regulation, when you book. Thanks!

Dragon In My Cabin By The Pool Jacuzzi and Sauna

(NO PARTIES, MAX AMOUNT OF PEOPLE ON PROPERTY IS 4) Make lasting memories with a unique experience in our dragon themed cabin. Enjoy lounging by the pool. Relaxing in the spa and sauna. Cookout on a full size wood grill or gas grille with access to the outdoor grilling area. Play your type of music with our pool surround sound system. Or get in some out doors recreation with the horse shoe pit, soccer field and basketball court.

Cozy Pine Tree Nest

This is a private, upstairs efficiency apartment over garage with stunning space features luxury laminate plank flooring, split unit a/c and heat, cherry wood beams harvested from the property, a full bathroom with tile/stone shower, pine ceilings, recessed lighting and a large deck to watch the amazing sun rises. Within minutes from Gambrill State Park, the Appalachian trail, restaurants, shopping, and downtown!

Garden View, a spacious 1 bedroom with loft.

Relax and unwind at this peaceful and charming retreat, nestled in a quiet neighborhood. Located just minutes from Route 50, I-95, and Downtown Annapolis, Garden View is ideally situated for exploring Naval Academy sports, the Renaissance Festival, Boat Shows, and golf at The Preserve. If you prefer staying in, the fully equipped kitchen and free Wi-Fi make it easy to work or cook from the comfort of your space.