Holiday Rentals in Maryland

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Maryland holiday rentals
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Best family friendly Maryland holiday rentals

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

1879 Downtown Annapolis Home With Koi Ponds And Gardens - Maryland
Maryland
07/03 – 07/04
HK$5249/nightfor 1 night

1879 Downtown Annapolis Home With Koi Ponds And Gardens

1 2
house , Annapolis
This Annapolis dwelling, a historic 1879 house in the downtown area, is situated 1.9km from Annapolis Harbour and within 48km of Baltimore attractions.
Sleeping up to 15 guests, this one-bedroom property boasts two bathrooms, a fully equipped kitchen, a garden with koi ponds, a patio with an outdoor fireplace and barbecue, plus free Wi-Fi and air conditioning; nearby activities include exploring Annapolis Harbour and enjoying the city's historical sites.
Tilghman | Pool | Private Dock | Pet Friendly - Maryland
9.4 15 reviews
Maryland
06/27 – 07/04
HK$7101/nighttotal: HK$49707 (7 )

Tilghman | Pool | Private Dock | Pet Friendly

3 2
apartment , Tilghman Island
This waterfront property on Tilghman Island is just 0.3 miles from the Tilghman Watermen’s Museum and within easy reach of other attractions like the Chesapeake Bay Maritime Museum and St. Michaels Museum. The house has consistently received excellent ratings for location, cleanliness, and overall experience.
The property offers 191 square metres of space, accommodating up to 6 guests in its 3 bedrooms and 3 bathrooms. Guests can enjoy a private pool, a spa tub, a garden, a terrace, a barbecue, and modern amenities like free Wi-Fi and a fully equipped kitchen.
Gaia House - Maryland
9.3 58 reviews
Maryland
08/19 – 08/23
HK$1236/nighttotal: HK$4944 (4 )

Gaia House

2 3
house , Annapolis
Gaia House, in Annapolis, is situated 6 kilometres from Annapolis Harbour and within a 32-48 kilometre radius of Baltimore attractions including the Inner Harbour and Historic Ships in Baltimore.
This two-bedroom property, offering 9 square metres of floor space, sleeps seven guests and features a fully equipped kitchen, private parking, Wi-Fi, air conditioning, and a patio with quiet street views.
Private Pool Getaway - Maryland
Maryland
07/07 – 08/07
HK$990/nighttotal: HK$30690 (31 )

Private Pool Getaway

2 4
apartment , Reisterstown
This Reisterstown flat offers a central Owings Mills location, placing you within a 20-kilometre drive of the Under Armour Performance Center and Oregon Ridge Nature Center.
With 74 square metres of living space, this two-bedroom apartment accommodates up to six guests and features on-site parking, Wi-Fi, a kitchenette, a communal swimming pool, and a garden.

Top cities

Best pet friendly Maryland holiday rentals

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

Game Days & Family Stays At Dog-friendly Home Near Navy Stadium W Private Fenced-in Yard - Maryland
10 21 reviews
Maryland
06/26 – 06/28
HK$5810/nighttotal: HK$11620 (2 )

Game Days & Family Stays At Dog-friendly Home Near Navy Stadium W Private Fenced-in Yard

4 7
apartment , Annapolis
This four-bedroom Annapolis holiday home, situated in the Admiral Heights neighbourhood, is 1.1km from the Navy-Marine Corps Memorial Stadium and 3.2km from both the city centre and the United States Naval Academy.
Sleeping nine guests comfortably, this self-catering property boasts a private garden with fire pit, a fully equipped kitchen with stainless steel appliances, two bathrooms, and parking, all within easy reach of Annapolis's key attractions.
Charming 1-bedroom Cottage With Ac In Cozy Harwood - Maryland
Maryland
06/27 – 07/04
HK$1932/nighttotal: HK$13524 (7 )

Charming 1-bedroom Cottage With Ac In Cozy Harwood

1 2
cottage , Riva
This Anne Arundel County holiday let is situated approximately 18 kilometres from the Patuxent River and 24 kilometres from the Chesapeake Bay, with London Town and Annapolis Harbour Centre a short 13 to 14 kilometre drive away.
This one-bedroom annex accommodates up to four guests and offers amenities including Wi-Fi, air conditioning, a dryer, and ironing board, with toiletries provided, and is conveniently located for South River Golf Links and Thanksgiving Farm Wines.
Pet-friendly Beach Getaway, Relax By The Bay! - Maryland
10 6 reviews
Maryland
09/10 – 09/13
HK$3530/nighttotal: HK$10590 (3 )

Pet-friendly Beach Getaway, Relax By The Bay!

3 7
apartment , Arnold
This Annapolis apartment, situated 14.8 km from Annapolis Harbour and 43.5 km from Baltimore's Inner Harbour and Camden Yards, offers convenient access to waterfront activities and city attractions.
This 188 square metre property features two bedrooms, three bathrooms, a fully equipped kitchen, free Wi-Fi, private parking, and a balcony; comfortably accommodating up to 15 guests.
Charming Coastal Retreat W Community Beach Dog-friendly & Mins To Downtown Annapolis - Maryland
Maryland
06/27 – 07/13
HK$3777/nighttotal: HK$60432 (16 )

Charming Coastal Retreat W Community Beach Dog-friendly & Mins To Downtown Annapolis

3 5
apartment , Highland Beach
This Arundel on the Bay flat offers waterfront community access with scenic views, situated 6.4 kilometres from Downtown Annapolis and 8 kilometres from the U.S. Naval Academy.
This 111 square metre flat accommodates up to nine guests with four bedrooms, two bathrooms, a private office, a family room with a sleeper sofa, and a large private backyard, all within proximity to Thomas Point State Park and bay paddling.

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

Heaven On Baltimore At Harborfront - Maryland
9.3 5 reviews
Maryland
08/19 – 08/23
HK$2151/nighttotal: HK$8604 (4 )

Heaven On Baltimore At Harborfront

1 3
apartment , Baltimore
Vacation rental listing with an excellent rating of 93% based on 5 reviews. You will stay in Baltimore.
Services and facilities include a washing machine, a fitness center and an elevator. Take advantage of the air conditioning in this apartment!
Global Luxury Suites Bethesda Chevy Chase - Maryland
8.2 667 reviews
Maryland
06/27 – 07/04
HK$2454/nighttotal: HK$17178 (7 )

Global Luxury Suites Bethesda Chevy Chase

1 2
apartment , Bethesda
This apartment is located in Bethesda's Woodmont Triangle South, a short walk from the Bethesda Metro Station and within easy reach of Walter Reed National Military Medical Center and Washington National Cathedral. It has received very good ratings for location, cleanliness, and overall user experience.
The apartment features a spacious living area with a sofa and a desk, perfect for both relaxation and work. It offers a range of amenities, including a fully equipped kitchen, a terrace for barbecuing, a swimming pool, a fitness centre, and a concierge service.
32-acre Farm, Pool • Hot Tub • Theater/game Room - Maryland
10 36 reviews
Maryland
07/24 – 07/27
HK$9590/nighttotal: HK$28770 (3 )

32-acre Farm, Pool • Hot Tub • Theater/game Room

5 10
gîte , Rock Point
This five-bedroom, five-bathroom holiday home in Rock Point, Maryland, is situated approximately 8km from the Potomac and Wicomico Rivers and a 16km drive from Budds Creek Raceway.
Sleeping ten guests, the property boasts a large kitchen, a heated saltwater pool (open Memorial Day to Labor Day), a seven-person hot tub, a games room, and 32 acres of private land offering stunning autumn foliage views.
Minutes From Downtown Easton And St. Michaels | Pool - Maryland
10 4 reviews
Maryland
07/24 – 07/27
HK$16081/nighttotal: HK$48243 (3 )

Minutes From Downtown Easton And St. Michaels | Pool

5 10
apartment , Oxford
This five-bedroom, three-bathroom apartment is located in Easton, Talbot County, Maryland, a waterfront property on Edge Creek offering access to attractions such as St. Michaels and the Chesapeake Bay Maritime Museum; note that this is not in Oxford as initially stated.
This 255-square-metre (2744 square feet) holiday home boasts a private pool, dock, and ample amenities for up to ten guests, including a fully equipped kitchen and air conditioning.

Best Maryland holiday rentals with parking

Beautiful 1900s Built 2br Downtown Loft - 9 Min Walk To Carroll Creek - Pets Ok - Maryland
10 3 reviews
Maryland
07/17 – 07/24
HK$2045/nighttotal: HK$14315 (7 )

Beautiful 1900s Built 2br Downtown Loft - 9 Min Walk To Carroll Creek - Pets Ok

2 5
apartment , Frederick
This 2-bedroom flat is located on the second floor in downtown Frederick, a short walk from Carroll Creek (under 10 minutes) and Nymeo Field (9 minutes), with The Weinberg Center For The Arts 0.8 kilometres away and Hood College and Frederick Health Hospital a 7-minute drive.
This property offers accommodation for up to 7 guests, featuring air conditioning, Wi-Fi, a fully equipped kitchen, a workspace, and sleeps up to 6 with 2 Queen beds and a Queen sofa bed, with a check-out time of 11:00 AM.
The Cozy Crab- Your Charming Haven In Lovely North Beach! - Maryland
9.8 23 reviews
Maryland
07/11 – 07/16
HK$1459/nighttotal: HK$7295 (5 )

The Cozy Crab- Your Charming Haven In Lovely North Beach!

1 4
apartment , North Beach
The Cozy Crab apartment is situated in Calvert County, Maryland, a short drive from attractions such as the Rod 'n' Reel Charter Fishing and Fridays Creek Winery.
This one-bedroom, one-bathroom self-catering flat sleeps four guests and features a fully equipped kitchen with appliances including a fridge, microwave, and dishwasher, plus air conditioning, a garden, and parking.
Lakefront A-frame: Private Dock, Kayaks & Sauna  Sleeps 12, Chesapeake Bay - Maryland
9.6 12 reviews
Maryland
07/04 – 07/05
HK$6745/nightfor 1 night

Lakefront A-frame: Private Dock, Kayaks & Sauna Sleeps 12, Chesapeake Bay

4 6
apartment , Chesapeake Ranch Estates
This four-bedroom, three-bathroom house in Lusby, Maryland, is a four-minute drive from Seahorse Beach and six minutes from Drum Point Lake, offering easy access to Annmarie Sculpture Garden and Arts Centre and Calvert Marine Museum.
The 279-square-metre (approximately 3000 square feet) property sleeps twelve guests and includes a fully equipped kitchen, laundry facilities, air conditioning, Wi-Fi, and parking; barbecue facilities are also available on-site.
Spacious 4-bedroom Townhouse  Perfect Fall Getaway In Silver Spring 34/50 - Maryland
Maryland
07/01 – 08/02
HK$1213/nighttotal: HK$38816 (32 )

Spacious 4-bedroom Townhouse Perfect Fall Getaway In Silver Spring 34/50

4 2
apartment , Cloverly
This Cloverly house, a spacious four-bedroom, three-bathroom property, is situated approximately 10 kilometres from the Patuxent River, The Adventure Park at Sandy Spring, Brookside Gardens, Olney Theatre Centre, and Gardens Ice House.
The self-catering residence comfortably sleeps six guests and offers convenient on-site parking, reliable internet access, in-house laundry facilities, and is in a smoke-free environment.
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