Vacation rentals near Chesapeake Bay

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Experience the enchanting charm of Chesapeake Bay, where scenic beaches meet vibrant local culture. Relax on the soft sands of Chesapeake and Outlook Beaches, or dive into thrilling water sports and outdoor adventures. Explore inviting neighborhoods like Silver Beach and Jamesville, perfect for families and groups seeking unforgettable experiences. Our diverse selection of vacation rentals, from cozy cottages to stunning beachfront homes, ensures you’ll enjoy ample space and home-like amenities for a truly memorable getaway.

Holiday rentals with weekly discounts - Chesapeake Bay

Showing deals for:Dec 11 - Dec 18

Image gallery for Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

Kitchen
10 out of 10, Exceptional, (30 reviews)
Exceptional
(30 reviews)

Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

Stevensville

12% off
Price is $281
$1,964 for 7 nights
All fees included
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

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Find out more about Chesapeake Bay

Why visit Chesapeake Bay

  • Outdoor Adventures: Enjoy a variety of activities like hiking, kayaking, and fishing in the stunning natural landscapes of Chesapeake Bay.
  • Beautiful Beaches: Relax at family-friendly destinations such as Chesapeake Beach, known for its semi-private beach atmosphere.
  • Cultural Experiences: Immerse yourself in the rich history and local culture of the area, with friendly locals welcoming you.
  • Diverse Accommodations: Choose from a range of vacation rentals, including cozy cottages and private homes, to suit your needs.
  • Scenic Beauty: Marvel at the breathtaking scenery, marinas, and nature reserves that make Chesapeake Bay a picturesque getaway.

Popular types of accommodation around Chesapeake Bay

Planning a getaway to Chesapeake Bay? Exciting times await as you choose the perfect place to stay. With a variety of options including houses, charming cottages, and cozy condos, you’re sure to find accommodations that fit your needs. Explore Chesapeake Beach vacation rentals and discover the beauty of vacation rentals in Chesapeake Bay. Your ideal vacation home or house rental is just a click away.

  • Houses: The top choice among travelers is Houses, offering spacious and comfortable accommodations perfect for families or groups.
  • Cottages: Cottages rank second, providing a quaint and cozy atmosphere ideal for a peaceful getaway by the water.
  • Condos: Condos come in third, featuring modern amenities and stunning views, perfect for enjoying the bay.
  • Cabins: Cabins are a charming fourth option, offering a rustic experience nestled in nature.
  • Apartments: Lastly, Apartments are a practical choice for those seeking convenience and a home-away-from-home feel.**

Top attractions near Chesapeake Bay

Chesapeake Bay is a fantastic destination for outdoor enthusiasts and beach lovers alike. With its stunning scenery, visitors can explore beautiful beaches, marinas, and nature reserves. The area offers a mix of cultural experiences and outdoor activities that cater to all types of travelers. Whether you're planning a relaxing vacation or an adventurous getaway, Chesapeake Bay has something to offer everyone.

  • Deltaville Marina: Experience the vibrant outdoor atmosphere at Deltaville Marina, where you can enjoy water sports, boat rentals, and stunning views of the Chesapeake Bay. This adventure hub is perfect for those seeking beach vibes and a chance to connect with nature.
  • Gwynn's Island Museum: Immerse yourself in local culture at Gwynn's Island Museum, where you can explore fascinating exhibits on archaeology and anthropology. This small gem showcases the rich history and heritage of the region, making it a must-visit for history buffs.
  • Cape Charles Beach: Relax at Cape Charles Beach, a beautiful stretch of sandy shoreline ideal for swimming, sunbathing, and picnicking. Enjoy the serene beach vibes while taking in breathtaking sunsets over the bay.

Things to do recommended for couples

Planning a romantic getaway to Chesapeake Bay? Visit Chatham Vineyards, just 11 miles away, where you can enjoy a delightful wine tasting amid a charming atmosphere. Embrace the romance and entertainment vibes that will make your couple's retreat truly unforgettable.

Things to do recommended for families

Families will delight in exploring the Chesapeake Bay Maritime Museum, where they can learn about local maritime history, or take a scenic boat tour to spot dolphins and other wildlife. Additionally, the sandy beaches at Sandy Point State Park offer a perfect spot for picnics and play.

Things to do recommended for groups

Explore the Northampton Shopping Center for fun shopping and entertainment vibes, or hit the links at the Eastern Shore Yacht and Country Club Golf Course and Golden Eagle Golf Club, both offering great outdoor sports experiences, all within a short drive from Chesapeake Bay.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Chesapeake Bay

When traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your preferences when filtering your options. Here are some helpful booking tips for using Vrbo.

  • Traveling to Chesapeake Bay with a group: Think about how many bedrooms you’ll require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Chesapeake Bay with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like private pools. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chesapeake Bay: For many families, a trip wouldn’t feel complete without their beloved pet. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that your furry friend feels just as comfortable as you do.
  • Planning for a long term stay visiting Chesapeake Bay: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the perfect spot. By using the right filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Chesapeake Bay

Chesapeake Bay offers a perfect blend of outdoor adventures and scenic beauty, making it an ideal vacation spot. Explore family-friendly destinations like Chesapeake Beach, where you can enjoy a semi-private beach atmosphere. The region is rich in history and friendly locals, ensuring a relaxing getaway. Discover the best Chesapeake Bay area attractions that cater to all budgets, creating unforgettable memories in this charming coastal paradise.

  • Silver Beach: Silver Beach is a charming village located 8 miles from Chesapeake Bay, offering a delightful outdoor and beach experience for families. Visitors can enjoy the scenic boardwalk and recreational areas, perfect for leisurely strolls and family outings. The nearby beach and nature reserve provide opportunities for relaxation and exploration, making it an ideal destination for those seeking a peaceful seaside retreat. With its tranquil atmosphere and beautiful surroundings, Silver Beach is a wonderful spot for beach lovers and nature enthusiasts alike.
  • Gwynn: Situated 10 miles from Chesapeake Bay, Gwynn is a vibrant city rich in cultural experiences and outdoor activities. Travelers can explore the local boardwalk and indulge in recreational areas or hit the golf course for some fun in the sun. The city is home to fascinating landmarks such as museums and archaeological sites, offering a unique blend of history and culture. With its inviting beaches and engaging activities, Gwynn is perfect for those looking to immerse themselves in both relaxation and adventure.
  • Jamesville: Jamesville, a quaint village located 10 miles from Chesapeake Bay, is the go-to destination for outdoor and adventure seekers. Visitors can explore recreational areas, hike scenic trails, and enjoy the local recreation parks. The proximity to stunning beaches and a national state park makes Jamesville an excellent choice for those who love nature and outdoor activities. Whether you're looking to hike, relax by the beach, or experience the beauty of the great outdoors, Jamesville promises a memorable vacation experience.

Best time to go to Chesapeake Bay

If you're planning a trip to Chesapeake Bay, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January38.7°F (3.7°C)Light RainMostly SunnySlightly LowSlightly Low
February42.1°F (5.6000000000000005°C)Light RainMostly SunnyAverageSlightly Low
March45.3°F (7.4°C)Light RainMostly SunnyAverageSlightly Low
April57.9°F (14.4°C)Light RainMostly SunnySlightly HighAverage
May66.6°F (19.200000000000003°C)Light RainMostly SunnyAverageAverage
June74.8°F (23.8°C)Light RainMostly SunnyAverageSlightly High
July79.5°F (26.4°C)Light RainMostly SunnySlightly HighSlightly High
August77.9°F (25.5°C)Light RainMostly SunnyAverageSlightly High
September72.7°F (22.6°C)Light RainMostly SunnySlightly HighAverage
October62.8°F (17.1°C)Light RainMostly SunnyAverageAverage
November51.4°F (10.8°C)Light RainMostly SunnySlightly LowAverage
December40.5°F (4.7°C)Light RainMostly SunnySlightly LowAverage

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Booking an extended stay can also lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve a qualifying Vrbo for your group getaway, you’ll earn OneKeyCash on the full booking amount. It certainly benefits you to be the trip planner. Become a member of our OneKey rewards program to unlock exclusive savings and earn OneKeyCash on eligible stays. Sign up today and begin reaping the rewards.

Vrbo Trips: Effortless planning

Vrbo's unique Trip Board offers you a convenient way to plan your travels, allowing you to start new trips, pick up right where you left off, or easily manage and review your plans. You can find the properties you've saved and booked categorized under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Stunning waterscapes in Chesapeake Bay

Straddling both Maryland and Virginia, Chesapeake Bay takes the crown of the largest estuary in the United States. Its shoreline is dotted with rolling farmlands and lush wetlands, as well as a handful of state parks and sandy beaches. You'll also find a handful of friendly towns and villages, each with their own unique personalities. Just across the Chesapeake Bay Bridge is the Eastern Shore, famous for its mouth-wateringly fresh seafood. If you want to reel in your own catch of the day, Chesapeake Bay vacation rentals unlock access to a stunning line-up of waterfront properties on the Eastern Shore.

Chesapeake Bay and the Star-Spangled Banner

Virginia's Chesapeake Bay region is brimming with history, from the birthplace of founding father George Washington to the estate of Confederate General Robert E. Lee. The Chesapeake Bay Maritime Museum in St. Michaels offers a glimpse at the region's colorful history, while mighty Fort McHenry served as the inspiration for America's beloved Star-Spangled Banner anthem. Beyond history, Chesapeake Bay boasts one of Virginia's most prestigious vineyards. Tucked away on the Northern Neck, Ingleside crafts award-winning reds, whites, and sparkling wine. With Chesapeake Bay vacation rentals you can stock up on your favorite blends then make a sunset toast on your own private deck.

Make a splash in Chesapeake Bay

Whether you want to paddle through Rocky Point State Park, kayak around the Chesapeake Ship Graveyard, or sign up for a hands-on fishing charter, there are endless opportunities to get your feet wet. Known as America's Sailing Capital, Annapolis is one of the bay's liveliest settlements. The historic city is anchored by a sprawling dock that attracts luxury yachts, high-speed powerboats, and everything in-between. Day trips to places like Smith Island, Oxford, and Chestertown offer a unique glimpse at colonial America, while Baltimore's Fells Point neighborhood serves up the bay's trendiest caf_s, bar, and restaurants.

Enjoy world-class birdwatching in Chesapeake Bay

Branching off the Atlantic Ocean, Chesapeake Bay is North America's largest estuary. It stretches for around 200 miles, which means there's a wealth of shoreline to explore. The seafood scene is legendary, with local specialties including blue crabs, clams, and oysters. The surrounding islands and wetlands also offer world-class birdwatching. From ospreys to bald eagles, the marshlands of Blackwater National Wildlife Refuge attract flocks of migratory birds traveling the Atlantic Coast.

How to get to and around Chesapeake Bay

The nearest airport is in Norfolk Intl. Airport (ORF), located 43.4 mi (69.8 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Newport News - Williamsburg Intl. Airport (PHF), which is 34.3 mi (55.2 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 vacation rentals near Chesapeake Bay?
The best vacation rentals near Chesapeake Bay are usually found in charming coastal towns and communities along its shores. You will find a great selection here, ranging from private vacation homes with waterfront access to comfortable apartments in historic districts. 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 tranquil surroundings. You will find many excellent options for the best vacation rentals near Chesapeake Bay.

Many top-rated rentals feature amenities so you can have a comfortable stay, such as a deck or patio for enjoying the bay breezes, and laundry facilities for longer stays. These homes are ideal for family getaways or guests looking to bring their pets.
Are there any cheap vacation rentals near Chesapeake Bay?
There are several affordable vacation rentals near Chesapeake Bay, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around $100 per night. Some stays even drop below this price in November 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 cozy private vacation homes to modest cottages, providing a clean, comfortable base for your stay.

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.
What are the best pet-friendly vacation rentals near Chesapeake Bay?
There are over 1,000 pet-friendly vacation rentals near Chesapeake Bay. These properties, including numerous private homes and apartments, are found in various towns surrounding the Bay. Many come equipped with amenities such as food and water bowls, and some offer private outdoor spaces for pets. Guests can expect comfortable living areas and kitchens in these rentals.

When searching for the best pet-friendly vacation rentals near Chesapeake Bay, remember to review individual property pet policies, as there may be restrictions on size or additional fees. While pets may have limited access to certain areas directly on Chesapeake Bay, many nearby public parks and green spaces offer ample opportunities for walks and outdoor activities.
What are the top vacation rentals with pools near Chesapeake Bay?
There are over 255 vacation rentals near Chesapeake Bay that include access to swimming pools, with options ranging from private backyard pools to shared community pools, and even indoor options. These properties are concentrated in various areas surrounding Chesapeake Bay. Many of these homes come fully equipped with amenities such as full kitchens, multiple bedrooms, Wi-Fi, and decks, making them ideal for families or groups looking for a comfortable stay.

When selecting your rental, consider whether a private pool for seclusion or a shared pool with potential access to additional features like hot tubs or fitness centers better suits your needs. For cooler months, look for heated or indoor options to ensure year-round enjoyment. Always check availability for peak summer dates to secure your preferred property.
What are the best family vacation rentals near Chesapeake Bay?
There are over 1445 family-friendly vacation rentals near Chesapeake Bay, with popular options including private vacation homes and cottages. These homes typically offer multiple bedrooms and bathrooms, providing ample space for groups. Many properties come equipped with full kitchens, washer/dryers, and outdoor play areas like yards or gardens. For entertainment, some rentals also feature games and video games.

When selecting a vacation rental, families should prioritize properties that offer distinct areas for adults and kids, and practical amenities like fully equipped kitchens to simplify meal preparation and laundry facilities for convenience. Staying close to Chesapeake Bay minimizes daily travel, allowing more time to enjoy the area's attractions.
Are there any luxury vacation rentals near Chesapeake Bay?
Near Chesapeake Bay, guests can find several luxury vacation rentals that combine natural scenery with modern comfort. These properties often feature amenities such as private pools, private beach access, gourmet kitchens, spa-style bathrooms with rainfall showerheads, and climate control for a comfortable stay. Guests can also enjoy views of the lake and the bay.

These homes are ideal for families or larger groups, offering conveniences like air conditioning and high-end bedding. Many of these top-tier stays are managed by highly rated Vrbo hosts, ensuring a professional and premium experience.
Where should I stay when visiting Chesapeake Bay?
When planning your stay near Chesapeake Bay, several areas offer distinct experiences. The Eastern Shore is a wonderful option, providing charming properties with easy access to the bay's tranquil waters and historic towns. This region is known for its picturesque landscapes and opportunities for water activities.

Another excellent choice is the Annapolis area. Here, you'll find rentals that place you close to the vibrant maritime culture and historic downtown, with many properties offering views or quick access to the bay. It's a great spot for those who appreciate both natural beauty and cultural attractions.

For a more secluded experience, consider areas along the western side of Chesapeake Bay in Virginia. These locations offer peaceful properties great for relaxation, often with private docks or waterfront access, allowing guests to fully enjoy the bay's serene environment.
What is the cheapest month to stay near Chesapeake Bay?
The cheapest time to find vacation rentals near Chesapeake Bay is typically during the late Autumn to early Spring months (November to March), excluding the Thanksgiving, Christmas, and New Year's weeks. January and February frequently offer the best deals on homes and properties, with rates often 20% lower than peak summer pricing. Guests can often find various savings and greater availability for vacation rentals during these colder months.
Are there any lakefront vacation rentals near Chesapeake Bay
Lakefront vacation rentals near Chesapeake Bay offer a great mix of comfort, scenery, and outdoor adventure. Many are located along the various coves and inlets of the Chesapeake Bay itself. These properties are a short drive from the main attractions, offering convenient access to water activities such as kayaking, fishing, or simply relaxing by the shore.

These homes often feature spacious decks, fire pits, hot tubs, and fully equipped kitchens, making them ideal for families or larger groups. Guests can enjoy water views and unwind in peaceful surroundings after exploring local trails.
Are there any top beachfront vacation rentals near Chesapeake Bay
Beachfront vacation rentals near Chesapeake Bay offer direct access to the water, with many properties featuring ocean-view balconies. Locations along the various shores of the Chesapeake Bay provide options ranging from lively areas with convenient access to dining and entertainment, to quieter, more secluded spots great for relaxation. Guests can easily find properties that allow them to step directly onto the sand or are just steps from the water.

These properties often include amenities such as beach chairs, umbrellas, and waterfront access, enhancing the stay for all guests. Accommodation types vary from ocean-facing rooms and suites to multi-bedroom properties with private terraces, suitable for different needs.
Are there any monthly vacation rentals near Chesapeake Bay?
Vrbo offers excellent options for monthly vacation rentals near Chesapeake Bay, making it a great choice for those who want to combine work and adventure. Monthly rentals often feel like a true home away from home, with fully furnished properties equipped with essential amenities like high-speed Wi-Fi, full kitchens, and comfortable workspaces, perfect for remote work or a summer vacation with the family. With flexible monthly rental options, Vrbo is a convenient and comfortable choice for extended stays near Chesapeake Bay.
Are there any last-minute vacation rentals near Chesapeake Bay?
Vrbo makes it simple to find last-minute vacation rentals near Chesapeake Bay that blend comfort, style, and great value. Vrbo offers plenty of options for guests ready to pack up and go. Families and groups will find these deals especially appealing. Many spacious homes, complete with full kitchens, private pools, and multiple bedrooms, often become available when hosts want to fill open dates on their calendars.

Finding these stays is easy. Just enter your destination and travel dates, then use Vrbo's "Last Minute" or "Discounts" filter to uncover the best offers. You'll see reduced rates in the listings. Vrbo's last-minute rentals are a smart way to save while you explore. Whether you're planning a quick trip or a weekend getaway with friends, your last-minute escape is waiting, you just have to decide where to go next.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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 Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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