Holiday Rentals in Maryland

57371 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Maryland holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Best Holiday rentals and Airbnb offers in Maryland

Best family friendly Maryland holiday rentals

Among the 57371 accommodations in Maryland, here are the 4 best family friendly rentals

Summer Getaway Near Dc And Baltimore Pool, Private Yard & Peaceful Setting - Maryland
9.8 19 reviews
Maryland
16/08 – 23/08
SG$653/nighttotal: SG$4571 (7 )

Summer Getaway Near Dc And Baltimore Pool, Private Yard & Peaceful Setting

3 2
apartment , Fairland
This 3-bedroom, 3-bathroom flat in Silver Spring, Fairland, is situated 35 kilometres from the Walter E. Washington Convention Centre and 26 kilometres from Merriweather Post Pavilion, offering convenient access to local attractions such as Ellsworth Place and Beltway Plaza, as well as entertainment venues like the Gardens Ice House and Xfinity Centre.
This family-friendly apartment accommodates up to six guests and features a fully equipped kitchen, air conditioning, Wi-Fi, a swimming pool, a garden, a terrace, and on-site amenities including a fitness centre and billiards table, with parking available.
First Floor Studio Apartment In Historic Chestertown - Maryland
9.7 290 reviews
Maryland
15/08 – 17/08
SG$188/nighttotal: SG$376 (2 )

First Floor Studio Apartment In Historic Chestertown

1 2
studio , Kingstown
This apartment is located in Chestertown, a short distance from Washington College and Rolphs Wharf Marina, offering easy access to cultural attractions and scenic waterfront views. The apartment has consistently received excellent ratings for location, cleanliness, and overall experience.
This self-catering home can accommodate up to three guests and offers a comfortable living space with a bedroom, a bathroom, and a fully equipped kitchen. The apartment comes with a range of amenities, including a private pool, a fitness centre, a spa, and a terrace, perfect for relaxing and enjoying the surrounding area.
182 M² House ∙ 3 Bedrooms ∙ 12 Guests - Maryland
9.6 18 reviews
Maryland
14/12 – 17/12
SG$380/nighttotal: SG$1140 (3 )

182 M² House ∙ 3 Bedrooms ∙ 12 Guests

3 5
house , Accident
This spacious three-bedroom house, perfect for families, is situated in Accident, Maryland, directly adjacent to Wisp Resort and a five-minute (8 km) drive from Deep Creek Lake.
The 182-square-metre property boasts an open-plan living area, a family theatre room, a private balcony with ski slope views, a swimming pool, hot tub, and sleeps up to ten guests, with easy access to local attractions including Deep Creek Lake State Park and Swallow Falls State Park.
Comfortable Villa - Maryland
Maryland
29/06 – 07/08
SG$412/nighttotal: SG$16068 (39 )

Comfortable Villa

5 3
house , New Carrollton
This five-bedroom Hyattsville villa, near New Carrollton, offers convenient access to Washington, D.C. and the University of Maryland, both within a few kilometres.
Sleeping up to 14 guests, the property boasts a full kitchen with dishwasher, a jacuzzi, and parking for four cars; nearby attractions include the National Mall and Six Flags America.

Top cities

Best pet friendly Maryland holiday rentals

Among the 57371 accommodations in Maryland, here are the 4 best pet friendly rentals

Charming Studio With All Amenities In Downtown Silver Spring - Maryland
Maryland
01/08 – 30/08
SG$140/nighttotal: SG$4060 (29 )

Charming Studio With All Amenities In Downtown Silver Spring

1 2
studio , Silver Spring
This Silver Spring studio apartment is located in the Downtown Silver Spring district, offering easy access to the Smithsonian Institution (approximately 10 kilometres away) and Union Station Shopping Centre (approximately 9.5 kilometres away).
This one-bedroom apartment accommodates up to four guests and features air conditioning, Wi-Fi, and a well-equipped bathroom, with a full bed and a futon for sleeping arrangements.
Private Suite: Hotel Perks, Snacks & Fast Wifi Near Baltimore & Top Hospitals - Maryland
Maryland
10/07 – 11/07
SG$258/nightfor 1 night

Private Suite: Hotel Perks, Snacks & Fast Wifi Near Baltimore & Top Hospitals

1 2
apartment , Overlea
This studio flat in Overlea is located in a rural Baltimore setting next to a golf course, offering easy access to local attractions and amenities, with the Baltimore Cruise Terminal and Baltimore Inner Harbor Marina approximately 8 kilometres away.
This garden-level flat, suitable for two guests, features a queen bed, modern bathroom, air conditioning, heating, a communal garden, and on-site fitness equipment, with a bus stop, shops, and highway access all within 1 kilometre.
302 M² House ∙ 3 Bedrooms ∙ 6 Guests - Maryland
Maryland
25/06 – 08/08
SG$176/nighttotal: SG$7744 (44 )

302 M² House ∙ 3 Bedrooms ∙ 6 Guests

3 2
house , Urbana
House rental for 6 people. This accommodation is located in Urbana.
Services and facilities include a washing machine, a fridge and a freeze. This house also has a garden!
Firefly Cottage At The Cape, Community Beach, Spring  Adventures, Hot Tub, Usna - Maryland
10 108 reviews
Maryland
17/07 – 24/07
SG$411/nighttotal: SG$2877 (7 )

Firefly Cottage At The Cape, Community Beach, Spring Adventures, Hot Tub, Usna

1 5
cottage , Arnold
This charming cottage is located in Cape Saint Claire, just a short drive from Arnold's attractions, including Sandy Point State Park and Sandy Point Beach. The cottage has received excellent user ratings, making it a popular choice for travellers.
This holiday home offers 61 square metres of space, comfortably accommodating up to 5 guests in its one bedroom and one bathroom. The cottage is equipped with a range of amenities, including a fully fitted kitchen, a spa, a terrace, a garden, parking and Wi-Fi, ensuring a comfortable and enjoyable stay.

Frequently asked questions about holiday rentals in Maryland

  • What are the must-see sights in Maryland, United States?

    For iconic Maryland sights, the Inner Harbour in Baltimore is a must, with its National Aquarium and historic ships. Then there's the United States Naval Academy in Annapolis, a stunning campus with a rich history. Fort McHenry in Baltimore, where the Star-Spangled Banner was inspired, is another key historical site. For a different perspective, explore the charming streets and architecture of historic Annapolis itself.
  • What are the best Airbnb and vacation rentals in Maryland?

  • Are there unique natural phenomena in Maryland, United States?

    Yes! Assateague Island National Seashore is famous for its wild horses. The Chesapeake Bay, the largest estuary in the United States, offers unique ecosystems and abundant wildlife viewing opportunities. You can also find stunning scenery in the Appalachian Mountains, which extend into western Maryland, offering hiking and breathtaking views.
  • What are the most popular Airbnbs in Maryland?

  • What essentials should you bring along for a trip to Maryland, United States?

    Comfortable walking shoes are a must, as are layers of clothing, as the weather can be unpredictable. Sunscreen and insect repellent are also recommended, especially during the warmer months. Don't forget a reusable water bottle, as staying hydrated is key, particularly when exploring outdoors.
  • What are the best vacation rentals with a pool in Maryland?

  • What famous events or festivals are happening in Maryland, United States?

    Maryland hosts many events. The Preakness Stakes, a prestigious horse race held annually in Baltimore, is a major event. Artscape, a large outdoor arts festival in Baltimore, is another popular choice. Numerous smaller, local festivals take place throughout the state, celebrating everything from seafood to local produce, depending on the time of year.
  • What are the best rentals for families and kids in Maryland?

  • Where can you find the best restaurants serving local dishes in Maryland, United States, and what are the must-try specialties?

    Baltimore's Inner Harbour area boasts many excellent seafood restaurants. Crab cakes are a Maryland staple, and you'll find countless variations. For a truly local experience, try Smith Island Cake, a unique layered dessert. Exploring different neighbourhoods will reveal many hidden gems offering delicious, authentic Maryland cuisine.
  • What are the best rentals or Airbnbs with a jacuzzi in Maryland?

  • What are some less-famous attractions in Maryland, United States that are worth a visit?

    Consider visiting the Catoctin Mountain Park, offering hiking and scenic views, or the Eastern Neck National Wildlife Refuge for birdwatching. The Chesapeake & Ohio Canal National Historical Park provides a peaceful escape and opportunities for cycling or walking along the historic towpath. These locations offer a quieter, more secluded experience than the more popular tourist spots.
  • What are the best activities for engaging with locals and understanding their culture in Maryland, United States?

    Visiting local farmers' markets is a great way to interact with Marylanders and sample regional produce. Attending smaller, local festivals can provide insights into community life and traditions. Simply striking up conversations with people in local bars or cafes can also offer a glimpse into the culture of the area.
  • What unique natural landscapes and terrain features can travellers explore in Maryland, United States?

    Maryland boasts diverse landscapes. The Chesapeake Bay offers stunning coastal scenery and waterways. The Appalachian Mountains in western Maryland provide opportunities for hiking and exploring mountainous terrain. The coastal plain in the east offers a different type of scenery, with beaches and wetlands.
  • How many days are ideal for a trip to Maryland, United States, and what are some itinerary suggestions?

    A long weekend (3-4 days) allows for a taste of Maryland's highlights, focusing on Baltimore and Annapolis. A week allows for a more in-depth exploration, potentially including a visit to the Eastern Shore or the Appalachian Mountains. A longer trip (10+ days) would allow for a more relaxed pace and the exploration of more niche interests.

Nearby regions

Best Maryland holiday rentals with a pool

Among the 57371 accommodations in Maryland, here are the 4 best rentals with a pool

121 M² House ∙ 2 Bedrooms ∙ 4 Guests - Maryland
Maryland
01/07 – 30/11
SG$145/nighttotal: SG$22040 (152 )

121 M² House ∙ 2 Bedrooms ∙ 4 Guests

2 1
house , Germantown
Vacation rental listing for 4 people. Your accommodation will be based in Germantown.
Services and facilities include a washing machine, a terrace and a freeze. Take advantage of the pool in this house.
Charming Cottage With Pool Access And Wifi In Lovely Rock Hall - Maryland
10 4 reviews
Maryland
11/08 – 21/08
SG$301/nighttotal: SG$3010 (10 )

Charming Cottage With Pool Access And Wifi In Lovely Rock Hall

1 2
cottage , Rock Hall
This Rock Hall cottage, ideally situated near the Waterman's Museum and The Mainstay, offers convenient access to Rock Hall Harbour and Rolph's Wharf Marina, all within walking distance (exact distances unspecified).
The 56-square-metre (approximately 600 square feet) self-catering property features a two-story layout with a king-size bedroom upstairs, a downstairs living area, and accommodates two guests; amenities include air conditioning, Wi-Fi, a mini-refrigerator, and a private pool (accessible May 1st to September 21st, 11 am to 5 pm).
"Endless Summer" Waterfront On The Chesapeake Bay! - Maryland
10 9 reviews
Maryland
10/09 – 13/09
SG$1219/nighttotal: SG$3657 (3 )

"Endless Summer" Waterfront On The Chesapeake Bay!

4 7
apartment , Madison
This Woolford holiday home is situated within 19 kilometres of Blackwater National Wildlife Refuge, the Harriet Tubman State Park Visitor Centre, and the Harriet Tubman Underground Railroad National Historical Park.
This four-bedroom, three-bathroom property sleeps twelve guests and boasts a private indoor pool, fully equipped kitchen, barbecue grills, smart TV, laundry facilities, and a patio area; enjoy easy self-catering and proximity to local attractions.
Comfy, Serene Home On Quiet Cul De Sac, Private Backyard Pool\nlic # Str23-00110 - Maryland
9.7 132 reviews
Maryland
17/07 – 24/07
SG$706/nighttotal: SG$4942 (7 )

Comfy, Serene Home On Quiet Cul De Sac, Private Backyard Pool\nlic # Str23-00110

4 5
apartment , Aspen Hill
This four-bedroom house is located in Rockville, just a short distance from F. Scott and Zelda Fitzgerald Gravesite, Pike & Rose, and Rockville Town Center. It has received excellent ratings for location, cleanliness, and overall user experience.
The property comfortably accommodates up to six guests and features a private outdoor pool and spa tub, a spacious garden, a fully equipped kitchen, and barbecue grills.

Best Maryland holiday rentals with parking

Beautiful Waterfront 2-bedroom Cottage In Tranquil Piney Point With Wifi, Ac - Maryland
10 5 reviews
Maryland
03/07 – 05/07
SG$446/nighttotal: SG$892 (2 )

Beautiful Waterfront 2-bedroom Cottage In Tranquil Piney Point With Wifi, Ac

2 4
cottage , Piney Point
This Piney Point waterfront holiday home is situated near St Mary's River State Park and the Piney Point Lighthouse, offering tranquil river views.
Sleeping up to six guests, the two-bedroom property boasts a fully equipped kitchen, air conditioning, Wi-Fi, smart TVs, and on-site barbecue facilities, making it ideal for families exploring the local area's attractions including the Patuxent River Naval Air Museum.
Chic Studio Retreat - Close To Dc & Top Attractions - Maryland
8.5 2 reviews
Maryland
01/08 – 30/08
SG$100/nighttotal: SG$2900 (29 )

Chic Studio Retreat - Close To Dc & Top Attractions

1 2
studio , Springdale
This studio apartment in Lanham offers convenient access to Washington D.C.'s attractions, situated approximately 21 kilometres from the Walter E Washington Convention Centre and the National Gallery of Art.
This non-smoking studio provides air conditioning, a fully equipped kitchen, free WiFi, and parking for up to two guests, with a check-out time of 11:00 AM.
Farmhouse On River, 12 Miles To Liberty Mountain - Maryland
9.7 145 reviews
Maryland
13/07 – 18/07
SG$443/nighttotal: SG$2215 (5 )

Farmhouse On River, 12 Miles To Liberty Mountain

5 8
house , Emmitsburg
This farmhouse is situated in Taneytown, Maryland, just 19 kilometres from Liberty Mountain and within easy driving distance of Gettysburg's historical sites. The property has received excellent ratings for its location, cleanliness, and overall experience.
This five-bedroom property spans 342 square metres and comfortably accommodates eight guests. The farmhouse offers a fully equipped kitchen, a garden, and parking, along with a range of amenities for a comfortable stay, including a flat-screen TV, towels, and bed linen.
Co's Corner - Maryland
9.4 21 reviews
Maryland
03/07 – 05/07
SG$322/nighttotal: SG$644 (2 )

Co's Corner

2 4
apartment , Baltimore
This two-bedroom townhouse is located in the Ridgely's Delight neighbourhood of Baltimore, just a short distance from Camden Yards, M&T Bank Stadium, and the Inner Harbour. The area is known for its historic charm and proximity to many of Baltimore's most popular attractions. This property has excellent user ratings, suggesting a positive experience for guests.
The townhouse is ideal for families or groups of up to six people. It features a range of amenities including free parking, internet access, and is pet-friendly, making it a convenient and comfortable option for travellers exploring Baltimore.
©2026 cozycozy.com