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Holiday rentals near Northern Chesapeake Bay

We found 1,571 holiday rentals — enter your dates for availability

If you want to to stay within easy reach of Northern Chesapeake Bay, scroll through and discover holiday rentals to find the perfect one for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include cable TV and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Northern Chesapeake Bay

Showing deals for:19 June - 26 June

Image gallery for Water View House in Charlestown, MD

Exterior
10 out of 10, Exceptional, (48 reviews)
Exceptional
(48 reviews)

Water View House in Charlestown, MD

Charlestown

8% off
Price is AU$3,946
for 7 nights, 1 home
AU$564 per night
includes taxes & fees
Water View House in Charlestown, MD

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Find out more about Northern Chesapeake Bay

Find the perfect holiday rental for your Northern Chesapeake Bay getaway

Learn about the unique charm of Northern Chesapeake Bay with a stay in a holiday home rental. This city's horse riding, sporting events and shopping draw many visitors. Local cultural sights include Washington Navy Yard and Smithsonian Institution. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Northern Chesapeake Bay

Are you searching for top things to see and do during your stay? Venture out of your cosy holiday rental and check out everything that makes Northern Chesapeake Bay a fun place to get away to. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • National Aquarium in Baltimore (25.9 mi / 41.7 km)
  • U.S. Naval Academy Golf Club (5.1 mi / 8.2 km)
  • Maryland Renaissance Festival (7.8 mi / 12.5 km)
  • Renditions Golf Club (10.3 mi / 16.5 km)
  • Lake Presidential Golf Club (14.4 mi / 23.2 km)
  • Six Flags America (15.9 mi / 25.5 km)

Exploring the natural landscape of Northern Chesapeake Bay

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Northern Chesapeake Bay is a great place to spend some time outside. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Maryland Quiet Waters Park (1.7 mi / 2.7 km)
  • Bay Ridge Beach (2.1 mi / 3.3 km)
  • Carrs Beach (2.2 mi / 3.6 km)
  • Triton Beach (2.9 mi / 4.6 km)
  • Smithsonian Environmental Research Center (4.7 mi / 7.5 km)
  • Shadyside Park (5.6 mi / 9.1 km)

How to get to and around Northern Chesapeake Bay

The nearest airport is in Fort Meade, MD (FME-Tipton), located 18.8 mi (30.3 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Baltimore Washington International Airport (BWI), which is 20.4 mi (32.8 km) away.

If you prefer to travel by train, Odenton Station, Bowie State Station and Lanham Seabrook Station are the main stations in the city. You can see more of Northern Chesapeake Bay by jumping on the metro at Cromwell-Glen Burnie Station, Largo Town Center Station or Ferndale Station.

Frequently asked questions

What are the best holiday rentals near Northern Chesapeake Bay?
The best holiday rentals near Northern Chesapeake Bay are typically located along the waterfront or in charming nearby towns in Maryland. You will find a great selection of private holiday houses and quaint cottages, many offering direct access to the water or stunning bay views. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties. You can choose from a range of styles to find the best holiday rentals near Northern Chesapeake Bay.

Many top-rated rentals feature amenities so you can have a comfortable stay, such as a deck or patio for outdoor dining and a blender for refreshing drinks. These properties are ideal for families or small groups looking for a relaxing coastal escape.
Are there any cheap holiday rentals near Northern Chesapeake Bay?
There are several affordable holiday rentals near Northern Chesapeake Bay, especially if you are flexible with location and travel dates. Budget-friendly stays typically start around AU$125 per night in areas like Island Park. Some stays even drop below AU$100 per night in November during the off-season, making it a great option for guests looking to experience the area without overspending. These rentals often include free amenities such as WiFi, toiletries, and self-parking, and can range from cosy studio cabins to modest family homes, providing a clean, comfortable base for adventure.

To get the best value, consider staying slightly outside major entrance towns like West Yellowstone. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. With a little planning, it is absolutely possible to find a comfortable stay near the park while keeping costs down.

*Pricing data are based on past 12 months data.
What are the best pet-friendly holiday rentals near Northern Chesapeake Bay?
There are hundreds of pet-friendly holiday rentals near Northern Chesapeake Bay, with 285 properties specifically welcoming pets. You will find a wide selection of private holiday houses and cottages in towns along the bay, offering essential amenities like fully equipped kitchens, Wi-Fi, and comfortable living areas. Many of these rentals also feature pet-specific comforts such as fenced yards, private decks, and easy outdoor access, ensuring a pleasant stay for both guests and their furry companions.

When searching for the best pet-friendly holiday rentals near Northern Chesapeake Bay, always review individual property house rules regarding pet size restrictions or additional fees. While pets are generally welcome in many outdoor areas around Northern Chesapeake Bay, specific beaches or nature reserves may have restrictions.
What are the top holiday rentals with pools near Northern Chesapeake Bay?
There are approximately 104 holiday rentals near Northern Chesapeake Bay that offer access to swimming pools, including both private and shared options. These properties, predominantly private holiday houses and cottages, are concentrated in areas along the bay's shoreline and in nearby charming towns. Many come equipped with standard amenities such as full kitchens, Wi-Fi, and outdoor decks, making them suitable for families and groups seeking a comfortable stay.

When selecting a rental, consider the benefits of different pool types. Private pools provide seclusion and are excellent for families, while shared pools often include access to additional amenities like fitness centres or hot tubs. For stays during cooler months, look for rentals with heated or indoor pool options. Checking availability for peak summer dates is advisable to ensure you secure your preferred property.
What are the best family holiday rentals near Northern Chesapeake Bay?
There are over 494 family-friendly holiday homes available in the Northern Chesapeake Bay area of Maryland. These homes typically offer ample space with multiple bedrooms and bathrooms, full kitchens for meal preparation, and often include outdoor play areas like gardens or secured yards. Many properties also provide essential amenities such as washer/dryers, and entertainment options like games and video games, ensuring a comfortable stay for all guests.

When selecting a holiday rental, families should prioritise properties that offer distinct sleeping areas for adults and children, and practical features like a well-equipped kitchen to make meal times easier. Staying close to Northern Chesapeake Bay means less travel time and more opportunities to enjoy the local attractions.
Are there any luxury holiday rentals near Northern Chesapeake Bay?
There are several luxury holiday rentals near Northern Chesapeake Bay that combine scenic views with modern comfort. These properties often feature amenities such as private pools, chef's kitchens, spa-style bathrooms, and premium bedding. Many homes also offer lake views, private beach access, and even onsite golf or tennis facilities.

These homes are ideal for families or larger groups, often providing efficient air conditioning and other comforts. Many of these top-tier stays are managed by highly rated Stayz hosts, ensuring a professional and premium experience.
Where should I stay when visiting Northern Chesapeake Bay?
When visiting Northern Chesapeake Bay, there are several appealing areas for holiday rentals, each offering a distinct experience.

The Upper Bay area, including towns like North East and Elkton, is excellent for those interested in outdoor pursuits such as fishing, boating, and hiking. Properties here often provide easy access to marinas and state parks, making it simple to enjoy the natural beauty of Northern Chesapeake Bay.

Further south, areas around Havre de Grace offer a charming historic setting. Guests can find rentals close to the waterfront promenade, museums, and local shops. This location provides convenient access to the confluence of the Susquehanna River and Northern Chesapeake Bay.

For a more secluded stay, consider properties along the quieter coves and tributaries of Northern Chesapeake Bay. These rentals often provide a peaceful escape with opportunities for wildlife viewing and private water access.
What is the cheapest month to stay near Northern Chesapeake Bay?
The cheapest time to find holiday rentals near Northern Chesapeake Bay is typically during the late Autumn (November) and early Spring (March-April). November frequently offers the best deals on homes and properties, with rates often 25% lower than peak summer prices. Guests can often find various savings and greater availability during these off-peak periods.
Are there any lakefront holiday rentals near Northern Chesapeake Bay
Lakefront holiday rentals near Northern Chesapeake Bay are readily available, primarily found along the various coves and inlets that feed into the bay itself. These properties are a short drive from Northern Chesapeake Bay, offering convenient access to water activities such as kayaking, fishing, swimming, or relaxing by the shore.

These homes often feature spacious decks, fire pits, hot tubs, and full kitchens, making them ideal for families and larger groups. Guests can enjoy water views, spot local wildlife, and unwind in peaceful surroundings.
Are there any top beachfront holiday rentals near Northern Chesapeake Bay
Beachfront holiday rentals near Northern Chesapeake Bay are often found along the shoreline, offering direct access to the water. Many properties boast water-view balconies, with some locations providing steps directly to the sand. While the Northern Chesapeake Bay area tends to be quieter, properties are typically a short drive from lively dining and shopping in nearby towns, allowing for both relaxation and easy access to amenities.

Guests can often find properties equipped with beach towels and, in some cases, beach sun loungers. Many rentals offer waterfront locations and ocean views, with amenities like kayaking and paddleboating often available nearby. Accommodation types typically include private holiday houses and cottages, many with multiple bedrooms and private outdoor spaces, ideal for families or groups.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Stayz customer service and Stayz™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare customer service is available 24/7 to support you every step of the way.

Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive.

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