Holiday Rentals in Maryland

57371 available vacation rental offers

7 nights
2
1
  • tripcom
  • booking
  • airbnb
  • tripadvisor
  • klook
  • agoda
  • expedia
  • hotelscom
  • hotelscombined
  • eztravel
  • makemytrip
  • rakutentravel
Maryland holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

Maryland holiday rentals: compare the best deals

Best family friendly Maryland holiday rentals

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

Waterfront Baltimore 2br Furnished Apartment Apts - Maryland
9.0 151 reviews
Maryland
07/11 – 07/16
HK$1925/nightTotal: HK$9625 (5 )

Waterfront Baltimore 2br Furnished Apartment Apts

2 4
apartment , Baltimore
This apartment is situated in Baltimore's waterfront district, just a short distance from Harbor East Marina, Pier Six Concert Pavilion, and Fell's Point, offering a lively and convenient location. It has been consistently rated very good for cleanliness, user experience, and location.
The apartment is well-equipped with a modern kitchen, a terrace, and access to a swimming pool, a jacuzzi, a fitness centre, and free parking. Guests can enjoy the convenience of a concierge service, a restaurant, and free Wi-Fi, making for a comfortable and enjoyable stay.
Cozy Getaway Near Harper`s Ferry, C&o & Potomac - Maryland
9.8 61 reviews
Maryland
07/17 – 07/20
HK$1058/nightTotal: HK$3174 (3 )

Cozy Getaway Near Harper`s Ferry, C&o & Potomac

1 2
apartment , Brunswick
This Brunswick apartment, situated in a historic building in the town centre, offers easy walking access to restaurants, shops, and the Chesapeake & Ohio Canal towpath, and is a short drive (a few kilometres) from Harpers Ferry.
The one-bedroom, one-bathroom flat sleeps four guests and includes a terrace, garden, spa, parking, and Wi-Fi; nearby activities include mountain biking trails and proximity to the Appalachian Trail and Harpers Ferry National Historical Park.
Dog Friendly! Next To Navy Stadium And Dta Shuttle! - Maryland
10 10 reviews
Maryland
07/13 – 08/14
HK$3179/nightTotal: HK$101728 (32 )

Dog Friendly! Next To Navy Stadium And Dta Shuttle!

2 5
apartment , Annapolis
This Annapolis holiday home is situated less than 1.6km from the U.S. Naval Academy and the Navy-Marine Corps Memorial Stadium, offering easy access to Helen Avalynne Tawes Garden and Peters Cove within a 10-minute drive.
The 111 square metre property comprises two bedrooms, one bathroom, and accommodates up to six guests, featuring a fully equipped kitchen, private patio, garden, parking, and free Wi-Fi.
Station House East: Upscale Loft In The Historic District Cambridge, Md - Maryland
10 7 reviews
Maryland
08/01 – 08/30
HK$1528/nightTotal: HK$44312 (29 )

Station House East: Upscale Loft In The Historic District Cambridge, Md

1 2
apartment , Cambridge
This flat is located in the historic Four Corners Building in Downtown Cambridge, a short walk to the Cambridge Marina, Choptank River waterfront, and Long Wharf Park.
This 98 square meter residence accommodates up to four guests with one bedroom and a king-size bed, featuring a fully equipped kitchen, private workspace, air conditioning, and Wi-Fi, with spa and parking facilities available.

Top cities

Best pet friendly Maryland holiday rentals

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

Stylish Studio Basement - Maryland
10 1 review
Maryland
06/25 – 08/08
HK$834/nightTotal: HK$36696 (44 )

Stylish Studio Basement

1 3
studio , Suitland
This newly remodelled basement flat in Southeast Washington offers convenient access to Joint Bases Andrews and Bolling, and is just a few kilometres from the centre of Washington D.C., with public transport within easy walking distance.
This studio apartment accommodates up to four guests, featuring a fully equipped kitchenette, air conditioning, and a full-sized washer and dryer, with dedicated off-street parking available.
Downtown 1br W/ Parking | Walk To Harbor & Stadium - Maryland
Maryland
07/11 – 07/16
HK$1499/nightTotal: HK$7495 (5 )

Downtown 1br W/ Parking | Walk To Harbor & Stadium

1 4
apartment , Baltimore
This city centre flat in Baltimore offers a prime location, just 200 metres from the Convention Centre, Oriole Park at Camden Yards, and the M&T Bank Stadium, with the University of Maryland Medical Center, Johns Hopkins Hospital, and Mercy Medical Center also close by.
This one-bedroom, one-bathroom flat accommodates up to four guests and includes a kitchen with a fridge, microwave, and dishwasher, air conditioning, and complimentary indoor parking, whilst being within walking distance of the Baltimore Inner Harbour Marina, Baltimore Cruise Terminal, and the CFG Bank Arena.
Mountain Escape - Maryland
8.6 31 reviews
Maryland
12/14 – 12/17
HK$2468/nightTotal: HK$7404 (3 )

Mountain Escape

2 5
house , Accident
This two-bedroom apartment is situated just 3.5 kilometres from Wisp Skiing and Golf Resort in Accident, Maryland, with easy access to the lake and a shared dock slip only a short walk away. It has received excellent ratings for location, cleanliness, and overall experience.
The property is both cosy and spacious, perfect for a small group. It offers a range of amenities including a fireplace, a jacuzzi, and a garden, allowing you to relax and enjoy the beautiful surroundings.
Annapolis Home | Fenced Yard | Pool Table | 10 Guests - Maryland
9.8 11 reviews
Maryland
07/01 – 07/31
HK$2733/nightTotal: HK$81990 (30 )

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

3 5
apartment , Arnold
This five-bedroom, two-bathroom house in Annapolis, Maryland, is situated approximately 9.6 kilometers from Sandy Point State Park and Beach, offering easy access to Annapolis attractions.
This spacious 1640 square metre property sleeps ten guests and boasts a fully equipped kitchen, terrace, garden, parking, Wi-Fi, and barbecue facilities, plus proximity to several golf courses.

Frequently asked questions about holiday rentals in Maryland

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

    For iconic Maryland sights, one must visit Baltimore's Inner Harbour, with its historic ships and National Aquarium. The United States Naval Academy in Annapolis is another must-see, showcasing impressive architecture and maritime history. For a taste of nature, the Chesapeake Bay offers stunning views and opportunities for water activities. Historic Annapolis itself, with its charming colonial architecture and shops, is a delightful place to explore. Finally, the state boasts numerous beautiful state parks, like Assateague Island National Seashore, known for its wild horses.
  • What are the best Airbnb and vacation rentals in Maryland?

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

    Yes, Assateague Island National Seashore is famed for its wild horses, a truly unique sight. The Chesapeake Bay, the largest estuary in the United States, is another significant natural phenomenon, supporting a rich ecosystem and offering opportunities for birdwatching and other nature-based activities. The Blackwater National Wildlife Refuge provides excellent opportunities for observing diverse bird species, particularly during migratory seasons.
  • What are the most popular Airbnbs in Maryland?

  • What essentials should you bring to Maryland, United States?

    Depending on the time of year, comfortable walking shoes are a must, as are layers of clothing to adapt to changing weather conditions. Sunscreen and insect repellent are advisable, especially during warmer months. A reusable water bottle is helpful, and an umbrella or raincoat could be useful as rain showers are possible throughout the year. Finally, a camera is essential to capture the beautiful scenery and historical sites.
  • What are the best vacation rentals with a pool in Maryland?

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

    Maryland hosts numerous events. The Preakness Stakes, a renowned horse race, is a major event held annually in Baltimore. Artscape, a large-scale outdoor arts festival, takes place in Baltimore, showcasing local and regional artists. Numerous smaller town festivals celebrate local produce and culture throughout the year; checking local event listings closer to your travel dates is recommended.
  • 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 has many restaurants offering fresh seafood. Crab cakes are a Maryland staple, found at numerous establishments. For a taste of regional cuisine, try restaurants in smaller towns across the state; they often feature locally sourced ingredients. Smith Island Cake is a unique dessert, a layered cake found on Smith Island in the Chesapeake Bay. Looking for specific restaurant recommendations requires more detailed location preferences.
  • 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?

    The Catoctin Mountain Park offers hiking trails and stunning views, less crowded than some of the more popular state parks. The Star-Spangled Banner Flag House in Baltimore, where the flag was sewn during the War of 1812, is a lesser-known but historically significant site. Exploring the charming towns along the Chesapeake Bay, like St Michaels, offers a quieter, more authentic experience of Maryland life.
  • What are the best activities for engaging with locals and understanding their culture in Maryland, United States?

    Visiting local farmers' markets allows interaction with producers and offers a taste of regional produce. Attending smaller town festivals and events provides opportunities to mingle with locals. Exploring the historic districts of Annapolis and other towns gives a feel for Maryland's history and architecture. Conversations with shopkeepers and restaurant staff can also offer insights into local life.
  • What unique natural landscapes and terrain features can travellers explore in Maryland, United States?

    Maryland's diverse geography includes the Chesapeake Bay, a vast estuary, offering opportunities for boating and fishing. The Appalachian Mountains extend into western Maryland, providing hiking and scenic vistas. The coastal plain stretches along the eastern shore, featuring beaches and wetlands. Assateague Island's unique ecosystem, with its wild horses and diverse birdlife, is another highlight.
  • 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, focusing on a particular region like Baltimore or Annapolis. A week-long trip allows for exploration of multiple regions, combining city exploration with visits to state parks and the Chesapeake Bay. A longer trip (10+ days) provides ample time to explore the state's diverse landscapes and smaller towns at a more relaxed pace. Specific itineraries depend on interests, but a combination of city and nature-based activities is recommended.

Nearby regions

Best Maryland holiday rentals with a pool

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

Private Boat Dock! Wye River Retreat In Queenstown - Maryland
Maryland
09/03 – 09/07
HK$15849/nightTotal: HK$63396 (4 )

Private Boat Dock! Wye River Retreat In Queenstown

5 4
house , Grasonville
This Grasonville holiday home is situated approximately 18 kilometres from the Chesapeake Bay Exploration Center, offering easy access to Annapolis and other attractions within a 48-kilometre radius.
This five-bedroom property boasts 418 square metres of floor space, comfortably accommodating up to 19 guests, and includes a private swimming pool, spa, and on-site boat dock with direct water access.
Less Than 1 Mi To Dtwn Waterfront Townhome In Cambridge! - Maryland
Maryland
07/10 – 07/18
HK$4920/nightTotal: HK$39360 (8 )

Less Than 1 Mi To Dtwn Waterfront Townhome In Cambridge!

3 3
house , Cambridge
This Cambridge townhome, less than 1.6km from the city centre waterfront and its attractions, offers convenient access to Cambridge's historic sites.
The 167 square metre property boasts three bedrooms, four bathrooms, a swimming pool, and parking, comfortably accommodating up to 11 guests and including a fully equipped kitchen and laundry facilities.
Maryland Vacation Rental With Private Pool And Dock - Maryland
8.0 1 review
Maryland
09/10 – 09/13
HK$4445/nightTotal: HK$13335 (3 )

Maryland Vacation Rental With Private Pool And Dock

4 7
house , Long Beach
This Maryland property, situated in Dowell, is approximately 13 kilometres from Annmarie Garden and the Calvert Marine Museum, offering a convenient base for exploring the region.
This four-bedroom, two-bathroom house boasts 186 square metres of floor space, accommodating up to 21 guests and featuring a private pool, dock, fully equipped kitchen, free Wi-Fi, and laundry facilities.
Shore Point Cottages - Maryland
9.2 824 reviews
Maryland
12/14 – 12/17
HK$2177/nightTotal: HK$6531 (3 )

Shore Point Cottages

4 5
house , West Ocean City
Shore Point Cottages are situated just 1.9 kilometres from Baja Amusements and 2.4 kilometres from Grand Prix Amusements, offering easy access to both entertainment and West Ocean City's attractions. The cottages have received excellent ratings for location, cleanliness and user experience.
This 37 square metre property can accommodate up to 4 guests and features a kitchen with fridge and microwave, a bathroom, a garden, a swimming pool, parking, internet access and air conditioning. Guests can enjoy a comfortable stay with amenities like a patio, a flat-screen TV, and a seasonal outdoor pool.

Best Maryland holiday rentals with parking

Co's Corner - Maryland
9.4 21 reviews
Maryland
07/03 – 07/05
HK$1964/nightTotal: HK$3928 (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.
Renovated Bungalow | Walk To Beach | Dog-friendly - Maryland
9.4 6 reviews
Maryland
06/26 – 06/27
HK$5789/nightfor 1 night

Renovated Bungalow | Walk To Beach | Dog-friendly

2 5
apartment , Mayo
This Edgewater holiday home in Mayo is situated 2.1km from London Town and 2.4km from South River Golf Links, with Annapolis Harbour Center and the Smithsonian Environmental Research Center within 9.7km.
This 94 square metre property sleeps six guests in two bedrooms and one bathroom, and boasts a fully equipped kitchen, Wi-Fi, air conditioning, a private garden with barbecue, and parking; ideal for families.
Private Basement Studio With Patio In Columbia, Md - Maryland
9.7 6 reviews
Maryland
07/03 – 07/06
HK$767/nightTotal: HK$2301 (3 )

Private Basement Studio With Patio In Columbia, Md

1 2
studio , Scaggsville
This private basement apartment in Columbia, Maryland, is situated 26 kilometres from Carroll Park and 27 kilometres from the University of Maryland – Baltimore, offering convenient access to local attractions.
This studio, spanning 51 square metres, accommodates up to three guests and features a kitchenette with a fridge, air conditioning, WiFi, a fireplace, and a patio, with free private parking and terrace access.
Citystay - Maryland
9.5 2 reviews
Maryland
07/03 – 07/05
HK$2019/nightTotal: HK$4038 (2 )

Citystay

1 4
house , Baltimore
CityStay, a detached house in Baltimore, is located between 2.1 and 2.7 kilometres from Fell's Point, the Power Plant, and the Historic Ships.
This non-smoking dwelling offers air conditioning, complimentary WiFi, a fully equipped kitchen, and private balcony, accommodating up to eleven guests across two bedrooms and four bathrooms.
©2026 cozycozy.com