Holiday rentals in Upper Marlboro

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Top-rated holiday rentals in Upper Marlboro

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

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Top guest favourite
The cottage is showcased amid a wooded setting, featuring a gravel parking area. A small covered porch is visible, accented by colorful chairs. Lush greenery surrounds the structure, and a glimpse of Mill Creek can be seen in the background.
Cottage in Annapolis
4.96 out of 5 average rating, 456 reviews

Relaxing Water Views - Mill Creek Cottage

Eclectic three level water view cottage in unique wooded location overlooking beautiful Mill Creek. Minutes from downtown Annapolis and the US Naval Academy; walk to Cantler’s Riverside Inn for crabs, convenient to US 50 and the Bay Bridge and Eastern Shore. Due to the stairs and loft, this accommodation may not be appropriate for toddlers and the mobility challenged Parties are not permitted. Please note that there is no water access on the property, but there is nearby public water access.

Top guest favourite
Home in Alexandria
4.97 out of 5 average rating, 1,084 reviews

Beautiful and spacious 3 bedroom

Beautifully decorated and spacious home in a charming, Alexandria neighborhood near the King Street metro and the shops and restaurants of Old Town. Just a 16 minute drive to downtown Washington DC, with a chef's kitchen and a relaxing great room. The house is also just a 10 minute drive to the new MGM Casino or the Gaylord Resort and Convention Center at National Harbor. The "no parties in house" rule is strictly followed. If you want to have a party or an event, this is not the place for you.

Top guest favourite
Guest suite in Bowie
4.99 out of 5 average rating, 153 reviews

Luxury 1BR/1BA Private Suite Close to DC!

Whether you’re looking for a place to stay a couple of days, weeks, or months, this luxurious basement apartment offers a spacious environment with the perfect touch of style, comfort, and sophistication. Enjoy the electric fireplace, office, reading nook, and your own private spa bathroom. This suite has a private entrance and is located in a very peaceful cul de sac with plenty of restaurants and shopping nearby. The home is located just 20 mins outside of DC. Not suitable for small children.

Top guest favourite
An exterior view showcases a private entrance framed by a wooden deck and a small seating area with two chairs. The red door stands out against the light grey siding of the building, with a pathway of stepping stones leading to it. Lush green grass surrounds the area.
Flat in Bowie
4.94 out of 5 average rating, 158 reviews

Just Like Home - Private Entrance Apt in DMV Area

288 SQ FT PRIVATE ENTRANCE Mother-in-law suite/ studio apt, full bed, sleeper sofa, roll-away single bed, full kitchen, bathroom with small shower stall, 65” Smart TV w/cable, Netflix & WiFi. No guests under 12 years of age. Location: Ft. Meade (14.4 miles), Annapolis (15 m), Andrews AFB (19 m), Washington DC (19 m), Baltimore (29 m) Nearby airports: DCA (23 m), BWI (27 m), IAD (48 m) Public Transportation: Metro Bus Stop (0.2 m), New Carrollton Station Metrorail, Amtrak, & Greyhound (9 m)

Guest favourite
A black and grey RV with large glass windows is shown, allowing ample natural light. The entrance features a small set of stairs leading to a deck with a railing, surrounded by vibrant greenery and potted plants. A patio area is visible nearby.
Camper van/Motorhome in Lanham
4.95 out of 5 average rating, 138 reviews

Luna the Destination Camper

Just outside the buzz of D.C., Chesapeake Hideaway offers a peaceful, romantic retreat in the heart of Lanham. Surrounded by the natural beauty of Prince George’s County, this cozy RV features a queen+full bed, soft lighting, and panoramic windows for golden sunset views. Enjoy intimate meals in the charming kitchenette, then unwind on your private deck. Whether you're stargazing or exploring nearby Lake Artemisia and Greenbelt Park, this is the perfect spot to relax and make lasting memories.

Guest favourite
Tiny home in Bowie
4.84 out of 5 average rating, 114 reviews

Access to Private Guest House with Patio/Firepit

Centrally located to Washington DC, Annapolis, Baltimore and Northern Virginia, this tiny house is in a rural setting that is close to any amenity thinkable; minutes from the Bowie Town Center boasting restaurants, shopping and entertainment for your enjoyment. Major highways are less than 10 min away and will have you on your way to your commute or seeing any of the major landmarks and places of interest that make the DMV a top area for both tourists and working professionals alike.

Superhost
The interior of the cottage features a vaulted wooden ceiling with beams, creating an open atmosphere. A spacious sectional sofa faces a wood-burning stove. The kitchen is equipped with modern appliances, while light streams through large windows draped in sheer curtains.
Guest house in National Harbor
4.92 out of 5 average rating, 770 reviews

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.

Guest favourite
A spacious swimming pool is surrounded by lush greenery, with colorful pool floats gently resting on the water's surface. A concrete deck provides access, and a handrail leads into the pool. A large screen for outdoor viewing is positioned nearby.
Flat in Upper Marlboro
4.94 out of 5 average rating, 201 reviews

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

Top guest favourite
Home in Upper Marlboro
4.97 out of 5 average rating, 114 reviews

Modern Escape | Near DC, Dining & Entertainment!

Discover the perfect blend of comfort and convenience! This stylish home is perfect for group trips, family getaways, or a relaxing retreat. Just minutes from FedExField, home of the Washington Commanders, and a quick Metro ride to downtown D.C., National Harbor, and Nats Park. Shop and dine at Woodmore Towne Centre, catch a movie at AMC Theatres, explore Watkins Regional Park, or enjoy top equestrian events at Prince George’s Equestrian Center. Unbeatable location—book now!

Top guest favourite
The exterior of a two-story home is displayed, featuring a light-colored façade, white porch railings, and a chimney. A neatly manicured lawn surrounds the house, complemented by tall trees in the background and a clear blue sky above.
Home in West River
4.97 out of 5 average rating, 156 reviews

Cozy waterview home in West River!

Your family will be close to everything when you stay at this centrally-located place. This home is located just 15 miles to Annapolis, 18 miles to the Naval Academy, and 30 miles to the heart of Washington, DC. Less then 8 miles to Rt 214, providing direct access to beltway, and other major highways. This charming home has as spacious fenced in yard, High Speed Internet, TV (Netflix & Hulu), outdoor seating and a fire pit. Want to get away? Bring the whole family!

Guest favourite
A spacious hot tub is showcased under a wooden pergola, illuminated by soft blue lighting. A control panel with multiple settings is visible on the back wall, enhancing the outdoor relaxation space. The surrounding area features a warm wooden finish.
Guest suite in Clinton
4.97 out of 5 average rating, 155 reviews

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.

Top guest favourite
A modern two-story house is displayed, featuring a spacious front porch with multiple columns and a well-maintained lawn. The exterior presents a combination of light gray siding and dark shutters, while a driveway leads to a garage on the right side.
Guest suite in Prince George's County
4.97 out of 5 average rating, 106 reviews

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.

Popular amenities for Upper Marlboro holiday rentals

Frequently Asked Questions

  • What are the best places to stay in Upper Marlboro?

    Accommodations around central Upper Marlboro place you near historic districts and local dining. Rural stays just outside town are frequently suggested for those seeking a quieter setting near parks and nature.

  • What are the best things to do in Upper Marlboro with kids?

    Watkins Regional Park is often recommended for its carousel, playground, and nature center. Family-friendly farms and seasonal fairs provide interactive activities for all ages.

  • What are some of the best things to do in Upper Marlboro?

    Explore Watkins Regional Park’s gardens and nature trails, or attend events at the Show Place Arena. Historic estates around town offer guided tours with context on the area’s social and cultural history.

  • How is the weather in Upper Marlboro?

    Upper Marlboro has cool winters around 30–45°F (-1–7°C) and warm, humid summers peaking near 90°F (32°C). Rain is common year-round, so bringing a light rain jacket is often practical.

  • When is the best time to visit Upper Marlboro?

    Late spring and early fall are frequently suggested for mild weather and community events, with temperatures around 60–75°F (16–24°C). Summer attracts visitors for outdoor festivals, while winter is quieter but can be wet and cool.

  • What are the best places to visit in Upper Marlboro?

    Watkins Regional Park draws families with its gardens and nature features, while the Show Place Arena hosts diverse cultural and community events. The area also has historic estates interpreting regional and social history.

  • What are some hiking trails in Upper Marlboro?

    The trails in Watkins Regional Park and Patuxent River Park are frequently suggested for walking, jogging, and nature observation. Both parks provide a mix of forest, wetland, and open space experiences.

  • What are some family activities we can do in Upper Marlboro?

    Families often explore Watkins Regional Park for its playgrounds, nature center, and seasonal attractions. Local farms and community festivals provide hands-on activities and learning experiences throughout the year.

  • What are some of the best day trip ideas from Upper Marlboro?

    Explore local vineyards, state parks, and nearby city museums for a change of pace. Local wildlife centers, gardens, and regional art spaces around the area are also frequently suggested.

  • Are there any pet friendly accommodations available in Upper Marlboro?

    Several stays in and around Upper Marlboro are pet friendly, particularly those near green spaces and parks. It is often helpful to check listing details and communicate your needs to hosts in advance.

  • What are some local tips for visiting Upper Marlboro?

    Exploring early in the day is frequently suggested for a more relaxed experience at outdoor parks and historic sites. Engage with local markets for fresh produce, and check community calendars for ongoing events or seasonal activities.

  • What is Upper Marlboro known for?

    Upper Marlboro is known for historic estates interpreting various aspects of regional history, agricultural fairs, and its proximity to nature reserves. The area also has a tradition of community gatherings at local event venues.

  • What are the best hidden gems to explore in Upper Marlboro?

    Patuxent River Park is often recommended for quiet hikes, birdwatching, and river views. Smaller heritage sites or local art spaces around town can offer a different look at community history and creativity.

  • What are the best foods to try in Upper Marlboro?

    Local cuisine includes Chesapeake-style seafood, pit barbecue, and dishes inspired by the diverse cultures of the region. Fresh produce from local farms is often featured in area markets and eateries.

  • What should I bring for a trip to Upper Marlboro?

    Pack layers for variable temperatures, especially between late fall and early spring, and a light rain jacket for frequent showers. Comfortable walking shoes are useful for outdoor sites and parks, while sunscreen is helpful during warmer months.

  • What is the nightlife in Upper Marlboro like?

    Upper Marlboro’s nightlife has a quieter atmosphere, with local bars, family owned restaurants, and occasional live music venues. For more vibrant nightlife, surrounding communities and nearby cities are frequently suggested.

  • What are the most popular events or festivals in Upper Marlboro?

    The Prince George's County Fair is often recommended for its agricultural displays, food, and local traditions. Seasonal events at the Show Place Arena bring together regional sports, markets, and cultural showcases.

  • Are there family friendly vacation rentals in Upper Marlboro?

    You will find family friendly rentals near Upper Marlboro’s parks, with options for extra bedrooms, kitchens, and outdoor play areas. Central neighborhoods and rural areas around town provide accessible stays for families.

Quick stats about holiday rentals in Upper Marlboro

  • Total holiday rentals

    Explore 10 holiday rentals in Upper Marlboro

  • Nightly prices starting at

    Upper Marlboro holiday rentals start at £45 per night before taxes and fees

  • Verified guest reviews

    Over 20 verified reviews to help you choose

  • Wifi availability

    10 of Upper Marlboro holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Upper Marlboro rentals

  • 4.9 Average rating

    Upper Marlboro stays are highly rated by guests – averaging 4.9 out of 5!