Pet-friendly vacation rentals in Southern Maryland

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

Waterfront on St. Leonard Creek at Fort Hill

Waterfront home on St. Leonard Creek w/ private pier for fishing and relaxing, PLUS a small beach area. Close to Solomons, fossil hunting at Calvert Cliffs, the Calvert Marine Museum (and their concerts), and other area attractions. Forget stairs! Our elevator directly connects the parking area to your private floor! Fort Hill is a uniquely quiet and private space with wide-open views of the outdoors. 15ft aluminum jon boat with 5hp outboard PLUS 4 kayaks are included FREE for you to enjoy!

Barnyard Retreat

We are BACK After a 2 year hiatus!! We cannot wait to see all of our wonderful guests again! Beautiful 750 sq. ft. in-law apartment set up in a very efficient setting with open living space and Jack-n-Jill bathroom. Space is very open with cathedral ceilings and sky-lighting. Apartment has it's own separate entrance and dedicated parking space. The apartment has fast, secure wi-fi and is set-up perfectly for traveling professionals. Please see additional info within our house rules section.

Beautiful Rural Suite near Washington, D.C.

Enjoy a rural environment only 50 minutes outside of Washington, D.C., and 45 minutes away from Andrew's Air Force Base. Located in a quiet wooded neighborhood with horses, goats, ducks, and more this property allows children space to run and play. Stores are less than 10 minutes down the road. This is a perfect little haven, fully equipped with a kitchen and laundry facilities. Parking is available for boats and trailers. Please Note: Sunday check-in is at 4pm, unless requested otherwise.

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l dates**

Levin's Waterfront Paradise @ Blackwater Refuge

Levin's paradise is a private and quiet campsite with gorgeous sunsets over Blackwater Wildlife Refuge! Wildlife abounds around the woodlands and marshlands that surround you in this secluded haven! The perfect place to rest and relax by the fire! You will find yourself a world away from it all, yet close to all of the wonderful attractions and dining that Cambridge has to offer! Bring your tent or camper (16 ft or less) and get off the grid! No water, electric or sewer hook ups!

Waterfront home, private dock

Relax right next to the water in this tranquil Montross getaway. Fish, crab, kayak, paddleboard, or just sit on the swing and watch dolphins, eagles, herons, and stingrays from your private dock. Dine outdoors on the spacious deck, spend some some quality family time with an in-ground trampoline, tree swing, cornhole, bocce ball, spikeball, and a unique custom-built treehouse. Or just stay inside, relax, and enjoy the views, with an indoor electric fireplace and jacuzzi bathtub.

Waterfront-View of Bay from your Bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

The Guest of Honor: Fenced Smart Home w/Hot Tub

This stylish ground-level only private space (Not a basement) is only 23 min from DC (30-35 min to downtown DC) 5 min from Andrew's Airforce Base, 15 min from the National Harbor & walking distance to Cosca Park. Cosca Park Amenities Include Baseball Fields, Outdoor Tennis Courts, Tennis Bubble, Walking Trail/Nature Trail, RestRooms, Playground, Skateboard Park, Paddle Boats on the Lake, Picnic Tables & Shelters, Nature Center, RV/Campground & parking lots.

The Lake Oasis Retreat *cozy, serene, relaxing*

Escape to The Lovers’ Lake Oasis, a cozy four-season retreat designed for romance and relaxation. Soak in the hot tub under soft twilight lighting, take in peaceful Placid Lake views, or unwind in the secluded backyard. On warmer days, walk five minutes to the dock and launch a kayak. For a special touch, add our romantic decor package with roses, candles, chocolates, and bubbly ($320) to enjoy while stargazing from the hot tub. Serenity awaits. 🍾🥂❣️

Quiet Luxury Home - Modern - King - 20 Min from DC

Completely new renovations with an eye for details have created a space that feels like a custom built home. Made to provide you with a memorable luxury rental experience. Comfortable, bright, modern, unique and stylishly furnished mastering the mix of timeless elegance and modern simplicity. An open floor plan space that’s equally welcoming and sophisticated, incorporating natural elements, layered fabrics, and textures.

Peaceful Waterfront Retreat on The Bay

Escape to a serene waterside cabin with a private dock on quiet St. Leonard Creek, just an hour from Washington, DC. This rustic studio offers a cozy retreat for solo travelers, couples, or small families looking for peace and relaxation. Whether you're here to unwind, work remotely, or explore the outdoors, you'll find plenty to enjoy—including two kayaks, two canoes, and stunning waterfront views.