Holiday houses in Cheltenham

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Top-rated holiday rentals in Cheltenham

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

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

LocationFamilyNearby

4.91 out of 5 average rating, 158 reviews

Top Guest favourite

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

FamilyLocationQuiet

4.96 out of 5 average rating, 177 reviews

Top Guest favourite

Home in Fort Washington

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!

LocationFamilyNearby

5.0 out of 5 average rating, 39 reviews

Guest favourite

Home in Largo

Modern Chic Getaway near DC & Fedex field + Metro

Bright, modern, and thoughtfully designed, this home blends comfort with style. Sunlight fills every room, cozy furnishings invite you to unwind, and sleek finishes make it feel special. Whether you’re working, exploring DC, or simply relaxing, this retreat adapts to your stay. Prime location near Metro, shops, dining & UMD Medical Center. Walk to FedEx Field, drive 20 mins to DC’s monuments & nightlife—convenience and comfort without compromise. Relax, explore, and feel right at home!

FamilyValueBathroom

4.92 out of 5 average rating, 63 reviews

Guest favourite

Apartment 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

FamilyValueIndoor spaces

4.94 out of 5 average rating, 218 reviews

Guest favourite

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.

Home in Fort Washington

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

ValueLocationBarbecue

4.9 out of 5 average rating, 175 reviews

Guest favourite

Home in Waldorf

Spacious 4BR Near DC | Free Parking | Sleeps 11

Spacious 4BR home in Waldorf, MD — 30 min from DC, free driveway parking, sleeps 11 across 4 bedrooms / 3 baths. WHAT YOU'LL LOVE • Sleeps 11 — great for big family trips and DC visits • Fully stocked kitchen, coffee maker, ice machine • In-unit washer/dryer, central A/C, fast WiFi, smart TVs • Free driveway parking + self check-in via smart lock Great for family reunions, military families near Joint Base Andrews, and DC visitors. We monitor Airbnb chat all day.

LocationFamilyBackyard

5.0 out of 5 average rating, 14 reviews

Superhost

Home in Waldorf

Private Pool | Modern | Lux 4 BR Retreat | 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.

FamilyLocationGetting around

4.84 out of 5 average rating, 123 reviews

Top Guest favourite

Home in National Harbor

7BR Group Hub: Mins to National Harbor & DC

This home has Two (2) seperate units (Connected by stairs located outside). Two gourmet kitchens, two laundry areas and plenty of outdoor patio space and parking. You will have the entire property to yourself. It sits on 5 wooded acres with deer that roam freely. The tranquil area is near the national harbor and the Tanger Outlets. A quick 13-minute drive into Alexandria and 20 minutes into Washington DC. It is a great place for groups. ×high chair available

ValueLocationQuiet

4.99 out of 5 average rating, 86 reviews

Guest favourite

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.

LocationValuePets

4.98 out of 5 average rating, 164 reviews

Top Guest favourite

A spacious living room features a large sectional sofa, adorned with decorative pillows in neutral tones. A dark coffee table sits in front, and the soft carpet adds warmth to the area. Two doorways lead to adjacent rooms, offering convenient access.

Guest suite in Prince George's County

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.

ValueLocationComfort

4.97 out of 5 average rating, 116 reviews

Guest favourite

Home in Fort Washington

Family Friendly Home near MGM

Relax in this newly built 2026 custom Colonial offering nearly 4,000 square feet of comfort and style. With 5 bedrooms, 5 full bathrooms, TVs in every room, private en-suite baths, and dedicated workspaces, this home is ideal for families, group trips, and business stays. Guests will love the open living area, chef’s kitchen, loft, enclosed deck, and attached 2-car garage.

FamilyLocationIndoor spaces

4.91 out of 5 average rating, 11 reviews