Holiday rentals in Cheltenham

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

Patuxent River View

🏡Stay at this peaceful, amenity‑rich guest house near North Beach, Chesapeake Beach, and Herrington Harbour, with quick access to Washington, DC, Baltimore, and Annapolis. Enjoy a fully stocked kitchen, coffee, fast WiFi, a seasonal pool, and a shaded gazebo designed for comfort and convenience. Perfect for wedding weekends, family visits, work trips, and quiet coastal getaways, this cozy home base makes it easy to relax, cook, stream, and recharge between festivities and exploring the area.

Cozy Woodside Home Near DC & National Harbor

Welcome to our veteran-hosted, family-friendly retreat in Upper Marlboro. Surrounded by peaceful woods, this cozy home offers the perfect mix of comfort, privacy, and convenience—just minutes from Northwest Stadium, MGM National Harbor, Tanger Outlets, Watkins Regional Park, and Washington, D.C. Whether you're here for family, business, or a weekend escape, you’ll enjoy a relaxing stay and a quiet place to recharge. Military & Business Travelers Welcome | Remote Work Friendly | Washer/Dryer

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.

The Parker House

Whether your taking a family vacation to the DC area or traveling for business. Avoid the crowds of the city and join us here in the peaceful suburbs of Upper Marlboro, MD. Easy access to the White House, Show Place Arena, National Museums, Smithsonian Zoo, The National Harbor and much more around the DMV area. Enjoy fun outdoors with 2 acres to run and play or with indoor games aplenty. Have a BBQ on the patio or relax by the firepit, let us help you relax and enjoy your stay!

Urban Cottage, MD minutes from DC/National Harbor

Come and enjoy our spacious detached cottage,lounge on your private back deck overlooking private parkland forests. A real urban escape in an excellent location! Just a few blocks away from the MGM Resort / Casino, National Harbor, and shopping. Across the river from historic Alexandria and 10-minutes from Washington,DC. Great for a solo adventure,couples,and friends (up to 4 guests). Enjoy the seasonal steam house and personal wood-burning stove if you book in the cold months.

*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.

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.

*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!

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.

Home Sweet Home! 3 bds | Bath | Kitch | Laundry

Stay and Relax with the whole family in this brand new spacious basement apartment with lots of room for fun. Easy access to the White House, Six Flags, Chesapeake Beach, National Museums, Smithsonian Zoo, and a host of other beautiful sights in the D.C., Maryland, and Virginia (DMV) areas. The nightly rate includes up to two guests, and there is a $20 per night charge for each additional guest staying overnight in the unit.

Weems Creek Cottage, Annapolis Waterfront

(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early. The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch. We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.