We found 1,042 holiday rentals — enter your dates for availability
Choose the right holiday rental within easy reach of Chesapeake Bay Bridge. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a washer and dryer. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Chesapeake Bay Bridge
Showing deals for:22 May - 29 May
Image gallery for Waterfront 4 BR home with private pier and boat dock
1010 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Waterfront 4 BR home with private pier and boat dock
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Frequently asked questions
What are the best holiday rentals near Chesapeake Bay Bridge?
The best holiday rentals near Chesapeake Bay Bridge are typically located in the charming areas of Annapolis and the surrounding coastal towns in Maryland. You will find a good selection here, primarily consisting of private holiday houses that offer ample space for a relaxed stay, along with some quaint cottages. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties. You can easily find the best holiday rentals near Chesapeake Bay Bridge to suit your preferences.
Many desirable homes feature amenities so you can have a comfortable stay, such as a DeckOrPatio superb for enjoying the views, a Fireplace for cooler evenings, and a Garden for outdoor relaxation. These properties are ideal for families or groups seeking a peaceful retreat by the water.
Are there any cheap holiday rentals near Chesapeake Bay Bridge?
There are several affordable holiday rentals near Chesapeake Bay Bridge, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around AU$290 per night. Some stays even offer good deals in March and January during the off-season, making it a great option for guests looking to experience the area without overspending. These rentals often include amenities such as WiFi, toiletries, and self-parking, and can range from cosy private holiday houses to modest cottages, providing a clean, comfortable base for adventure.
To get the best value, consider staying slightly outside major hubs. 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 Chesapeake Bay Bridge while keeping costs down.
*Pricing data are based on past 12 months data.
What are the top holiday rentals with pools near Chesapeake Bay Bridge?
There are several holiday rentals near Chesapeake Bay Bridge that feature swimming pools. While private holiday houses with their own pools are the most common type, some properties may offer shared community pools. These properties are often found in areas surrounding Annapolis, providing convenient access to the bridge. Many of these homes are well-appointed with essential amenities such as fully equipped kitchens, comfortable living areas, and Wi-Fi, making them suitable for families or groups seeking a relaxing stay.
When selecting your rental, consider whether a private pool for exclusive use or a shared pool with potential additional community facilities best suits your preferences. For warmer months, availability for properties with outdoor pools can be high, so it is wise to confirm your reservation in advance.
What are the best family holiday rentals near Chesapeake Bay Bridge?
There are 18 family-friendly holiday rentals available near the Chesapeake Bay Bridge, primarily private homes. These properties offer ample space with multiple bedrooms and bathrooms, full kitchens for meal preparation, and often feature outdoor play areas such as patios, gardens, or secured yards. Many also include essential family amenities like washer/dryers, and entertainment options such as WiFi, books, and even video games.
When selecting a home, consider properties that provide separate spaces for adults and children to relax, and prioritise those with practical features like a well-equipped kitchen and laundry facilities to simplify your stay. Choosing a rental nearby means less travel time and more opportunities to enjoy the area and the Chesapeake Bay Bridge itself.
Are there any luxury holiday rentals near Chesapeake Bay Bridge?
Near Chesapeake Bay Bridge, there are several luxury holiday rentals that combine the scenic waterfront with modern comfort. These properties often feature amenities such as private pools, elegant fireplaces, and lake views. Guests can also find options with private chefs available and opportunities for onsite golf or tennis.
These homes are ideal for families or larger groups, offering features like air conditioning and spacious living areas. Many of these top-tier stays are managed by highly rated Stayz hosts, ensuring a professional and premium experience.
How much is a holiday rental near Chesapeake Bay Bridge?
Holiday rentals near Chesapeake Bay Bridge offer a wide range of options to suit different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties typically start around AU$290 per night, providing an affordable option. Mid-range rentals, including private homes, are generally around AU$660 per night, offering more comfort and amenities. Upscale options can cost AU$940 or more per night, providing premium locations and luxurious features.
Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.
*Pricing data are based on past 12 months data.
Where should I stay when visiting Chesapeake Bay Bridge?
When visiting Chesapeake Bay Bridge, several areas offer excellent holiday rental options. Annapolis, just a short drive from Chesapeake Bay Bridge, provides a charming historic setting with a variety of properties available. Guests can enjoy the maritime heritage and many local attractions.
Across the Chesapeake Bay Bridge, Kent Island is another fantastic option. This area offers a more relaxed, waterfront experience with properties providing access to boating and fishing. It's an ideal choice for those seeking a tranquil escape with convenient access to Chesapeake Bay Bridge.
For those looking for a blend of historical charm and convenient access, areas within a short driving distance of Annapolis offer a range of holiday rentals.
What is the cheapest month to stay near Chesapeake Bay Bridge?
The cheapest time to find holiday rentals near Chesapeake Bay Bridge is usually during the late Winter to early Spring (January to March), excluding any local festival periods. January is frequently the single cheapest month, often providing better deals on properties and homes. Rates can be lower during these months, and guests often find various savings compared to the peak summer season.
Are there any lakefront holiday rentals near Chesapeake Bay Bridge
Lakefront holiday rentals near Chesapeake Bay Bridge are readily available, primarily found along the various coves and inlets of the Chesapeake Bay itself. These properties are a short drive from Chesapeake Bay Bridge, offering convenient access to water activities such as kayaking, fishing, sailing, and swimming, or simply relaxing by the shore with beautiful water views.
These homes often feature spacious decks, fire pits, hot tubs, and full kitchens, making them ideal for families and larger groups. Guests can enjoy the water and natural surroundings, making the most of the year-round appeal, from summer boating to cooler weather relaxation.
Are there any top beachfront holiday rentals near Chesapeake Bay Bridge
Beachfront holiday rentals near Chesapeake Bay Bridge are typically found along the shores of the Chesapeake Bay, offering direct access to the sand and often featuring water-view balconies. While the immediate vicinity of the bridge offers scenic views, properties are usually situated in nearby coastal communities, providing walkability to lively dining and local shops. For those seeking a quieter stay, there are also secluded beachfront homes a short drive away.
Guests can enjoy amenities such as beach sun loungers, beach towels, and water sports equipment for activities like kayaking and paddleboating. Many units provide comprehensive beach amenities for a comfortable day by the water. Accommodation types range from private holiday houses to cottages, many featuring ocean-facing rooms or multi-bedroom layouts with additional living space.
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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