Holiday rentals in Cheltenham

4.91 out of 5 average rating, 157 reviews

A stylish bar area is showcased with a pool table in the foreground and a sleek bar counter adorned with emerald green stools. Pendant lighting hangs from the ceiling, providing modern illumination, while a television is mounted on the wall for entertainment.

Home in Waldorf

*Brand New | Modern | Lux 4 BR | Huge | 24 m to DC

Dee's Lounge will offer you the ULTIMATE perfect stay! Indulge in a luxurious and refined experience that is sure to leave you feeling refreshed, relaxed, and rejuvenated! This space is designed to make you feel like you've escaped your everyday life. Whether it's a girl trip, family time or hanging with your friends, you are sure to have an amazing time! We are readily available to accommodate your needs and make sure that you enjoy your time here! UPDATE 7/17 Grass room is under construction

4.97 out of 5 average rating, 174 reviews

The exterior of a historic Italianate brick home features a light-colored facade with large windows. Adjacent, the interior showcases a stylish living area with a chandelier above a seating arrangement. A bright dining area is set for a meal, highlighted by large windows and elegant decor.

Home in Old Town

Historic Apothecary | 2 Master Suites | Old Town

Majestic, pre-Civil War Italianate brick home in favored southeast Old Town. Steps away from King Street and 2 blocks to the waterfront, location is unbeatable! This 3-story home established in the 1800s served as a former apothecary. New renovations offer utmost luxury, distinctive architecture with genuine hospitality and true sense of history and charm. 2 Masters Suites 4K 65in TVs w/ Streaming Hi-Speed Internet Dedicated Workspace 24 hr Self Check-in Washer/Dryer Free parking upon request

Townhouse in Upper Marlboro

Brand-New- Rooftop Luxe 4BR/5BA, 15 Min to DC+ MGM

New retreat-cozy, modern, luxe. This 4-bedroom, 5-bath home spans 2,800 sq ft with refined finishes and a thoughtful layout. Each room features luxe design, high-speed WiFi, and a smart TV with Netflix and Samsung TV. A dedicated home office with printer, scanner, and multiple monitors keeps work productive. Three outdoor seating areas, including a rooftop terrace with a cozy fire pit, invite outdoor time. 15 min to DC/National Harbor; 10 min to Commander Field. Ideal for short or long stays!

5.0 out of 5 average rating, 44 reviews

5.0 out of 5 average rating, 36 reviews

The Royal Estate

Welcome to the Royal Estate – Your Luxurious Home Away from Home! Step into luxury and comfort at The Royal Estate, a stunning 6-bed, 4.5-bath oasis located in the heart of Fort Washington. Perfectly positioned just moments away from the vibrant MGM National Harbor, this expansive single-family home promises an unforgettable getaway for families, friends, & groups alike. You’ll have exclusive access to the entire home allowing space to create special memories. Your royal experience awaits!

4.94 out of 5 average rating, 17 reviews

Farm stay in Brandywine

Convenient Cozy Farm Cottage 15 Miles from DC

Welcome to your tranquil escape at our luxurious Farm Cottage nestled within a serene 40-acre private estate where everything you need is within easy reach. Located just a stone's throw away from Rte 301, shopping, culinary, and convenience meets comfort in this idyllic countryside setting. Offering a seamless blend of modern amenities and rustic charm, the cottage boasts a cozy ambiance with tastefully appointed interiors, providing a welcoming atmosphere for relaxation and rejuvenation.

4.94 out of 5 average rating, 215 reviews

Flat in Upper Marlboro

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

The exterior of a spacious brick home is displayed, featuring a prominent front porch and multiple windows that allow for natural light. A well-kept lawn with neatly trimmed shrubs enhances the entrance. A paved driveway leads to a garage with ample parking space.

4.9 out of 5 average rating, 173 reviews

SPACIOUS Single Home near DC & National Harbor

Welcome this spacious single-family home relaxing by the waterfront for your getaway. It is perfect for vacations, retreats, meetings, and BUSINESS travelers. Create memories , beautiful experiences while enjoying a STUNNING lovely 6 bedrooms & 5 full Bath home with landscape garden, LUXURY settings, large custom kitchen, and EXQUISITE main suite ,close to Washington, National Harbor, MGM casino, Alexandria, and Tanger outlets. Provide one roll paper towel per stay

Superhost

Home in Waldorf

*Brand New | Modern Farmhouse | Lux 4 BR | Near DC

Relax with the whole family at this peaceful estate. Newly Remodeled Modern Farmhouse. Enjoy a stylish master bedroom with a double shower and deep freestanding soaker tub. Plenty of areas to relax in and watch movies or enjoy the beauty of the 100-foot-tall trees on the spacious 2-acre lot. Have fun with the Queen-sized bunk beds or if you have a little work to do you can use the home office complete with docking station, web cam and double large screen monitors.

4.83 out of 5 average rating, 119 reviews

4.89 out of 5 average rating, 229 reviews

Inground Pool | Hot Tub | Sauna | Theme Room

Enjoy the comfort of this fully remodeled, beautifully decorated single family home. Located minutes from National Harbor Waterfront, MGM, Tanger Outlets, restaurants and shops, and just 20 minutes from Washington, DC and DCA Airport. Situated on half an acre, the home features a brand-new in-ground pool for summer enjoyment, plus a private hot tub and indoor infrared sauna for year-round relaxation. Please supervise children and follow posted rules for safety.

4.98 out of 5 average rating, 163 reviews

A spacious living area features a brown leather sectional sofa, a large wall-mounted television, and soft natural light coming through the windows. An outdoor hot tub offers a relaxing retreat with calming blue water and integrated controls, while a cozy bedroom includes a modern dresser and an electric fireplace.

Guest suite in Clinton

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.

A large two-story home is shown in a serene natural setting, surrounded by trees displaying autumn foliage. The front porch features a welcoming entrance, while two garage spaces are visible beneath a symmetrical façade. Solar panels are installed on the roof, enhancing sustainability.

4.94 out of 5 average rating, 47 reviews

Home in Fort Washington| DMV

Enjoy a brand-new feel in this spacious and stylishly updated 4-bedroom, 2.5-bath Fort Washington home — just minutes from National Harbor, MGM Casino, Topgolf, Tanger Outlets, and major attractions in Washington, D.C. and Downtown Alexandria. With new flooring throughout, a renovated kitchen and master suite, plus a private patio, sunroom, and pool table, this home blends comfort, space, and convenience—an ideal alternative to hotels.