Fitness-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.

Biking · Hospitality · Amenities

Alice’s DelRay Cottage-Elegant/EV enabled Retreat

This is a beautiful 1938 cottage with gardens on all 4 sides of the property for drinks w/ Friends or grilling with Family. There are multiple skylight sources of natural light. The office space will support any collaboration requirement. Relax in the gardens while your car is plugged into the ChargePoint EV Charger. This is a very comfortable house for any season or length of stay. The house, patios and gardens make an excellent gathering spot for friends and associates to reconnect and relax.

Parks · Biking · Air conditioning

Waterfront 4-BR home w/ hot tub & charging station

Immaculately maintained 4-bedroom waterfront home + home gym on Cobb Island with water views from every window! Four beach cruiser bikes & private dock w/ 4 kayaks, to enjoy the peaceful Neale Sound. Hot tub + private deck off of the kitchen. Wall of windows inside the home, flooded w/ natural sunlight. Views of the sound & the river side of the island. 3 BR are large (2 King beds/1 Queen), w/ their own BA (1 BR w/ BA is on 1st floor, no stairs). Smart TV's in 3 BR's. Great entertaining space!

Biking · Sleep quality · River

Charming 1BR Apt | 5 Min to DC | Gym

Experience the joy of returning to this meticulously crafted, modern & elegant 1-bedroom apartment in Rosslyn, Arlington. Boasting an unbeatable prime location, everything you desire is just steps away. Take a morning coffee trip to Georgetown, visit the best DC tour sites, and grab dinner and shop in Rosslyn Arlington, all within 5-mins drive, metro, or a bus ride from the unit! ★5 Min to Reagan National Airport ★10 Min to White House ★5 Min to Georgetown Waterfront ★7 Min to Pentagon Mall

Parks · Comfort · Accuracy

Historic Manor - Main House

Nestled near the Chesapeake Bay and located just under an hour outside DC, it's the perfect getaway spot for time in nature making memories with family and friends. The Manor sits on almost 3 acres making it feel secluded and private while being close to the attractions, beaches and restaurants of the area. *The Manor has additional units on the property. Each unit is separate with private entrance. No indoor space is shared. Only the exterior property grounds are shared by other guests.

Parks · Hiking · Hospitality

Luxury Modern Home on Water+Hotub- Annapolis 25min

Waterside mid-century modern home, perfectly appointed. Join with colleagues, family, and friends. Paddleboard, roast marshmallows, watch fireworks, take a hot tub or team building. Our "Flight Deck" is perfect for meetings and retreats. Breathtaking, peaceful grounds with an abundance of space. Approximately 2800 SF sits on a 3/4 acre property - perfect for lawn games and zip lining. 20x20 furnished deck + dock Mayo Beach and Beverly Triton 1 mile away. Within an hour of the DMV

Hiking · Parks · Comfort

Spacious Townhome Near DC | Garage & Workspace

Take a video tour by scanning the code! Indulge in luxury and comfort at our meticulously designed 3 bedroom, 2.5 bathroom haven, perfect for big families, groups, or those seeking an unforgettable getaway. Nestled minutes away from Washington DC, Arlington, and Old Town Virgina. This is more than a place to stay; it's an immersive experience in luxury living. Welcome to your home away from home, where luxury meets convenience, and every detail is designed to elevate your stay.

Parks · Indoor spaces · Walkability

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

Bathroom · Pets · Cleanliness

Modern 4-Story Townhome Retreat Minutes From DC

Modern 4-level townhome in Parkside at Westphalia! This 3BR, 3.5BA retreat features a gourmet kitchen with double ovens, spacious living areas, and a private rooftop terrace. Enjoy a luxe primary suite, free parking, and request access to private resort-style amenities: pools, gym, clubhouse, game room, theater, and more. Minutes from DC, National Harbor, Joint Base Andrews, PG Equestrian Center, and Commanders stadium. Stylish, comfortable, and perfect for your next stay .

Family · Indoor spaces · Check-in

5-BR Home near DC Metro -Free Parking/Full Kitchen

RARE FIND — Main-Level Bedroom & Bath with No Steps! Welcome to your stylish D.C. retreat! This fully renovated 5-bedroom, 4-bathroom home offers 3,500 sq ft of open-concept living, just 3 minutes from the Metro and 10 minutes from the White House. Enjoy free street parking. Perfect for families or business travelers with a main-floor bedroom, chef’s kitchen, double living rooms, fast Wi-Fi, and smart TVs. Book your stay today and experience D.C. in comfort and style.

TV · Indoor spaces · Nearby

Studio Tower

Welcome to Placemakr Dupont Circle, a beautifully restored 1903 mansion that blends history with sophistication. It’s the perfect retreat, featuring queen beds, modern kitchenettes, and stylish bathrooms. Consider it an ideal home base after exploring Washington, D.C.’s many highlights — from boutique shops and galleries to countless museums and iconic landmarks like the White House, National Mall, and other must-see sights.

Comfort · Walkability · Location

Relaxing Retreat on the Hudson

Come escape to my 5-bed, 2-bath home on Hudson Creek! Featuring a deep pier with great crabbing, fishing, and boating, plus a bubbling hot tub and modern amenities throughout. Perfect for large groups, it comfortably hosts 15! Explore with complimentary kayaks, stay productive with WFH setups in every bedroom, and use my EV charger. Create unforgettable memories by the water.

Quiet · Check-in · Outdoor spaces