Kid-friendly holiday rentals in Southern Maryland

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

Fabulous 4-5 bedroom 3-bath house with spectacular views on a lush, waterfront point! Shady waterfront lawns & sunny pier, breezy open spaces, sparkling views, & wildlife. Hidden but close to services. Couples & groups love our wonderful, nature-filled spot, a fun, relaxing, serene retreat on the WEST shore of the Chesapeake (close proximity to D.C., Annapolis, Baltimore)! Crabbing, kayaks, fire pit on two country-like acres. See “NEW Amazing” for whole 6-7 bed 4 ba listing of same house.

Flint Hill Bright and Spacious Basement Apt, WiFi

This spacious and light-filled unit is perfect for touring Washington, DC with the whole family. It is the lower level, with separate entry, of a large family home. 25-30 minutes to downtown driving or by Metro. We are a short car/cab ride to the Vienna metro station. Many beds, a kitchenette, laundry machines, and a playset in the backyard for the littles. Street parking is by permit for up to one car. Put your feet up after trekking around; we’ve got board games and complimentary popcorn.

Lakefront/Dock, Woods, 3 Beaches, Kayaks, Hot tub

Our 3 bed/2 full bath+loft house sits in the woods surrounding a beautiful freshwater lake in a neighborhood on the stunning Potomac River! Come enjoy the nearby attractions or simply do nothing at all! We have kayaks/boats for your use right off the private dock. The community has 3 beaches: a private sandy lake beach with a swimming dock, a river-front sandy beach with 15 million+ old shark teeth, and a fossil cliff beach. Fishing! Hot tub on the patio! Bald eagle sightings! Theater Room!

Historic Apartment, centrally located DnTwnFXBG!

Immerse yourself in the charm of Fredericksburg's historic district with this captivating 1st-floor apartment with nearly 500 sqft, a group of up to 4 will sleep comfortably. Boasting a modern-boho style, this delightful space offers a large bedroom, full bathroom, & a fully-equipped kitchen that opens up to a spacious living and dining area. A large screen TV in the living space provides indoor entertainment after a night out! This is #1 of 3 of our apartment listings in the building!

Lakeside 2-Bedroom Suite

Waiting to welcome you to our treasured peaceful lakeside living. Hot tub, swimming pool and canoe available to complete a family adventure. Two bedrooms joining a bath (more suitable for children and parents or 2 cozy couples); private sunny living room overlooking gardens and bird sanctuary on lake. Fish from property or by our canoe. Friendly, quiet suburb in beautiful Virginia countryside, but one hour drive to Washington DC for city life and adventures. Relaxation at its best!

Private Cottage on gated estate

Completely remodeled guest cottage on gated, private estate. Home is located just minutes from Eastport, Downtown Annapolis, and the Naval Academy. (4.7 miles to the main gate). We are on a private well but we have installed a state of the art water softener, filtration system, and a blue light bacteria zapper. Home and grounds are kid friendly offering amply outside play space and a multipurpose sports court. Third bedroom of home has a full-sized crib, baby gates, and a twin bed.

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

Bayside Cottage- In the Town with views

Welcome to Bayside Cottage, a newly renovated beach cottage in the very charming (Town of Colonial Beach), Virginia! The cottage boasts 3 bedrooms and 2 full baths and is centrally located in town. Walk across the property to Bayside Marina, where you can watch the sun go down on the rooftop deck with a drink in hand (contact host for instructions) Bayside Cottage was recently fully renovated and is best suited for groups of 6.

Spacious Family Retreat in Tranquil Neighborhood

Our home is one of the largest homes in the neighborhood. It is beautifully decorated for your enjoyment. Our large family room will make you feel like you are at home. House is 2,700 sq ft. The house is a close 2.5 miles from the well-known National Zoo. Also, 0.7 miles to the METRO station that has a direct route to the National Mall - a perfect tourist destination.