Vacation rentals near Chesapeake Bay

We found 4,556 vacation rentals — enter your dates for availability

If you want to to stay within easy reach of Chesapeake Bay, take a look at vacation rentals to find the perfect home base for your trip. Whether you’re staying in a vacation home with family or friends, you'll find the best amenities for hanging out with the people that matter most, including parking and a TV. Whatever you're looking for, you're sure to find a rental for everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Chesapeake Bay

Showing deals for:Jun 12 - Jun 19

Image gallery for Newly updated 3 bedroom cottage with Solo Stove fire pit

The view from the front door
9.6 out of 10, Exceptional, (20 reviews)
Exceptional
(20 reviews)

Newly updated 3 bedroom cottage with Solo Stove fire pit

Reedville

9% off
Price is $231
$1,619 for 7 nights
All fees included
Newly updated 3 bedroom cottage with Solo Stove fire pit

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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 is the most popular type of vacation rental accommodation in Chesapeake Bay?
According to our data, condos are considered the most popular property type in Chesapeake Bay. But of course, everyone's idea of an awesome stay can vary. Vrbo has vacation homes with every size, shape and budget in mind, so you're sure to find the perfect fit.
How much does it cost to rent a vacation rental in Chesapeake Bay?
Property type, length of stay and season are some of the things that can determine the price of a vacation home. Simply enter your dates of travel to find your perfect escape. From cozy chalets to expansive villas, all Vrbo vacation rentals offer terrific value.
How much does it cost to rent a beach house in Chesapeake Bay?
When you travel and the style and size of the property will influence how much you'll pay for your beachside stay. Click on your Chesapeake Bay travel dates to see your options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use the filters to choose the features and amenities you want in your vacation home.
Are there pet-friendly vacation rentals in Chesapeake Bay?
Pack a bone and a squeezy toy for your pup because Chesapeake Bay has 824 properties that roll out the welcome mat to doggie guests. Let your four-legged buddy join in on the family trip at one of our pet-friendly vacation rentals on Vrbo. Simply enter your destination and dates, then check the "Pets allowed" filter box.
Are there large group vacation rentals in Chesapeake Bay?
Chesapeake Bay has 1,215 vacation rentals that can cater to 10 or more people. These properties come with plenty of space to share good times with friends and family.
What are the top attractions for families in Chesapeake Bay?
There are plenty of amazing things to see and do with the family in Chesapeake Bay, such as:

  • Virginia Beach Boardwalk
  • National Mall
  • White House

Are there one-bedroom vacation rentals in Chesapeake Bay?
Yes, Chesapeake Bay has 2,081 one-bedroom rentals available. Often located in sought-after areas thanks to their smaller size, a one-bedroom vacation rental is great if you're getting away with your partner or a buddy. And with plenty of home comforts like kitchens and more privacy, you'll be able to kick back and relax while sightseeing around this incredible destination.
Can I find two-bedroom vacation rentals in Chesapeake Bay?
Gather your nearest and dearest and enjoy a relaxing escape in one of the 2,163 two-bedroom vacation rentals Chesapeake Bay has to offer.
Are there vacation rentals with WiFi in Chesapeake Bay?
Whether you want to keep up to date with the news, look over emails or update your social media, there are 3,011 vacation homes with WiFi in Chesapeake Bay. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Chesapeake Bay?
Chesapeake Bay has 6,968 vacation rentals where you'll be able to wind down in air-conditioned comfort. To find a property on Vrbo that features this amenity, choose your travel dates and use the handy filters to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in Chesapeake Bay?
The minimum age permitted can vary across properties on Vrbo, so be sure to look at the rules of the vacation home in Chesapeake Bay you want to book. But typically, it's 16, 18 or 21.
How long can I rent a vacation rental in Chesapeake Bay for?
The length of time you can rent a vacation rental in Chesapeake Bay differs according to the property. Just enter your desired travel dates to display a list of options offering extended stays. With tons of amenities such as full kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to discover a terrific place to call your home away from home in Chesapeake Bay.
Does Vrbo offer discounts for vacation homes in Chesapeake Bay?
Overnight trip or extended vacation, Vrbo has some bargain deals and special discounts in Chesapeake Bay to match your style and budget. Take a look at our weekly and monthly discounts on vacation rentals, or see what's just been added with one of our newly listed homes. Whatever kind of getaway you're after, you'll find the ideal place to stay — without breaking the bank.

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