Holiday rentals near Chesapeake Bay

We found 4,601 holiday rentals — enter your dates for availability

If you'd like to stay close to Chesapeake Bay, take a look at holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with family or friends, you'll find the amenities that you need and want, which might include air conditioning and a pool. At the end of the day, you're sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Chesapeake Bay

Showing deals for:3 July - 10 July

Image gallery for USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR

View from the front of this Stately Masterpiece (you'd think I built it ;-)
8.0 out of 10, Very good, (5 reviews)
Very good
(5 reviews)

USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR

Annapolis

16% off
Price is AU$12,826
for 7 nights, 1 home
AU$1,832 per night
includes taxes & fees
USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Find out more about Chesapeake Bay

Take in the waterfront beauty of Chesapeake Bay

Enjoy the area's festivals, history and monuments with a rental holiday home in Chesapeake Bay. This welcoming city is known for its sporting events, live music and bird watching. Local cultural sights include Washington Navy Yard and Smithsonian Institution. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Chesapeake Bay

Do you want to discover attractions to see while you're in town? You'll be sure to enjoy Chesapeake Bay for its bird watching and boating. Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Chesapeake Bay a one-of-a-kind holiday spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Bay Creek Golf Club (19.5 mi / 31.4 km)
  • Compass Entertainment Complex (20.5 mi / 33 km)
  • Chatham Vineyards (10.6 mi / 17 km)
  • Golden Eagle Golf Club (19.6 mi / 31.6 km)
  • Good Luck Cellars (21.3 mi / 34.3 km)
  • SouthEast Expeditions (23.4 mi / 37.7 km)

Exploring the natural landscape of Chesapeake Bay

Whether you're an outdoor enthusiast or just want to take in the scenery, Chesapeake Bay is a great place to get outside. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Bethel Beach Natural Area Preserve (11.1 mi / 17.9 km)
  • White Stone Beach (17.6 mi / 28.4 km)
  • Cape Charles Beach (18 mi / 28.9 km)
  • Cape Charles Harbor (18.3 mi / 29.4 km)
  • Hughlett Point Natural Area (18.8 mi / 30.3 km)
  • Cuba Island (25.2 mi / 40.5 km)

How to get to and around Chesapeake Bay

The nearest airport is in Newport News, VA (PHF-Newport News - Williamsburg Intl.), located 34.3 mi (55.2 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Norfolk, VA (ORF-Norfolk Intl.), which is 43.4 mi (69.8 km) away.

If you prefer to travel by train, Williamsburg Transportation Center, Newport News Station and Virginia Beach Station are the main stations in the city. You can get around Chesapeake Bay by catching a ride on the metro at Ft Norfolk-Medical Center Station, Newtown Road Station or York Street-Free Mason Station.

Frequently asked questions

What are the best holiday rentals near Chesapeake Bay?
The best holiday rentals near Chesapeake Bay are typically located in charming waterfront towns and villages along the Bay's edge. You will find a great selection here, with many options for private holiday houses offering direct access to the water or stunning views, alongside comfortable apartments. If you are willing to drive a bit further, renting in nearby areas can be an affordable option for finding larger properties and enjoying the scenic drives.

Many top-rated rentals feature amenities so you can have a comfortable stay, such as patios or decks for outdoor dining and enjoying the views, and laundry facilities which is great for longer stays. These homes are ideal for families or small groups looking for a relaxing coastal escape.
Are there any cheap holiday rentals near Chesapeake Bay?
There are several affordable holiday rentals near Chesapeake Bay, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around AU$120 per night in areas like Annapolis. 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 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 while keeping costs down.

*Pricing data are based on past 12 months data.
What are the top holiday rentals with pools near Chesapeake Bay?
There are approximately 255 holiday rentals near Chesapeake Bay that offer access to swimming pools, including both private backyard pools and shared community facilities. Properties, primarily private holiday houses and condos, are concentrated in areas along the Bay's shores, offering a range of options from outdoor pools great for summer to indoor pools for year-round enjoyment. These homes often feature full kitchens, Wi-Fi, and spacious living areas, making them excellent choices for families or groups seeking a comfortable stay.

When selecting your ideal rental, consider the benefits of each pool type. Private pools provide seclusion for families, while shared pools often include access to additional amenities such as fitness centres or hot tubs. For stays during cooler months, looking for heated or indoor pool options will ensure a pleasant experience.
What are the best family holiday rentals near Chesapeake Bay?
There are over 1,400 family-friendly holiday homes in the broader region surrounding Chesapeake Bay, offering ample space and comfort for groups of all sizes. These rentals often boast multiple bedrooms and bathrooms, full kitchens, and generous living areas, all designed with families in mind. With such a wide selection, you can find stays with outdoor play areas, gardens, yards, and patios where kids can play, WiFi for downtime, and washer/dryers to handle laundry during the trip.

When choosing the best fit for your family, focus on properties where adults and kids each have space to unwind, and look for homes with practical amenities like well-equipped kitchens to save on dining out. Staying nearby can mean less travel each day and more time enjoying the surroundings.
Are there any luxury holiday rentals near Chesapeake Bay?
There are several luxury holiday rentals near Chesapeake Bay that combine scenic views with modern comfort. These properties often feature amenities such as private heated pools, private beach access, gourmet kitchens with private chefs, spa-style bathrooms with rainfall showerheads, and premium bedding with Egyptian cotton sheets. Many homes also include climate control cooling, fireplaces, and golf or tennis facilities on-site.

These homes are ideal for families or larger groups, offering conveniences like air conditioning and designer toiletries. 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 Chesapeake Bay?
When planning a stay near Chesapeake Bay, several areas offer distinct advantages for guests seeking holiday rentals.

The Annapolis area, on the western shore, provides a charming setting with historic properties and easy access to the bay's sailing culture and waterfront activities. Guests here can enjoy the city's amenities and maritime heritage.

For those desiring a more relaxed, natural environment, the Eastern Shore offers numerous picturesque towns and secluded properties. Areas like St. Michaels or Easton provide opportunities for enjoying the bay's seafood, wildlife, and tranquil scenery. These locations are excellent for a peaceful retreat.

Further south, properties around the Virginia Beach area offer proximity to the bay's southern reaches, with additional access to ocean beaches and family-friendly attractions. This combines the appeal of the bay with broader coastal experiences.
What is the cheapest month to stay near Chesapeake Bay?
The cheapest time to secure holiday rentals near Chesapeake Bay is typically during the late Autumn (October to November) and early Spring (March to April). November is frequently the single cheapest month, often offering better deals on properties compared to the peak summer season. You can often find various savings on homes and cottages during these cooler months, with rates potentially being 20-25% lower than in summer.
Are there any lakefront holiday rentals near Chesapeake Bay
Lakefront holiday rentals near Chesapeake Bay offer a great mix of comfort, scenery, and outdoor adventure. Many are located along the various tributaries and inlets that feed into Chesapeake Bay. These properties are a short drive from Chesapeake Bay, offering convenient access to water activities such as kayaking, fishing, swimming, or simply 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 wildlife, and unwind in peaceful surroundings after exploring local trails.
Are there any top beachfront holiday rentals near Chesapeake Bay
Beachfront holiday rentals near Chesapeake Bay offer direct access to the water, with many properties featuring ocean-view balconies or being just steps from the sand. Guests can find properties along the various inlets and shores of Chesapeake Bay, providing both secluded, quieter spots for relaxation and locations within walking distance of lively dining, shopping, and local attractions.

These holiday rentals often provide amenities such as beach chairs, umbrellas, and in some cases, onsite dining. Accommodation types range from individual homes to multi-bedroom units with private terraces, suiting different group sizes and preferences. Many properties offer ocean-facing rooms or suites.
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.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.