Photo by Ronanne Vinson

Chesapeake Beach holiday rentals

Q: What is the most popular type of holiday rental accommodation in Chesapeake Beach?

Based on our research, houses are the most sought-after holiday property type in Chesapeake Beach. But as you might expect, everyone's idea of an awesome stay is bound to be different. Vrbo has holiday homes with every shape, size and budget in mind, so you're sure to discover your ideal match.

Q: How much does it cost to rent a holiday rental in Chesapeake Beach?

Several things influence how much you pay for a holiday rental in Chesapeake Beach, like the length of stay, season and type of property. But, all of our holiday homes have something in common — excellent value. Just add your travel dates to find your ideal escape.

Q: How much does it cost to rent a beach house in Chesapeake Beach?

The average price for a holiday rental near the beach in Chesapeake Beach depends on when you're going and the style and size of property you're searching for. You can easily find prices on Vrbo by entering your preferred travel dates. Then use the handy filter tool to choose the number of bedrooms and amenities important to you, such as air conditioning, WiFi and a hot tub.

Q: Are there pet-friendly holiday rentals in Chesapeake Beach?

Yes. There are. You can choose from seven holiday rentals that allow pets in Chesapeake Beach. Plenty of our pet-friendly holiday rentals even have a garden for your four-legged fur baby to run around in, dog beds, complimentary treats and proximity to parks and green space. Apply the "Pets allowed" filter to find your pawfect pad on Vrbo.

Q: What are popular rental amenities in Chesapeake Beach?

When it comes to rental amenities that guests are looking for in Chesapeake Beach, a nearby waterfront, nearby museums and a water view are at the top of the list. With Vrbo holiday homes, there are options to match your style and taste, whether you're going on a holiday with family, friends or even pets.

Q: Are there large group holiday rentals in Chesapeake Beach?

With six Chesapeake Beach holiday homes that can accommodate five or more people, you can invite a few extra pals or family members along. Whether you're planning an informal get-together or a special event, we'll help you find a comfy space to match the occasion.

Q: Are there holiday rentals in Chesapeake Beach that welcome kids?

With seven family-friendly holiday properties to pick from in Chesapeake Beach, now is a fantastic time to introduce your children to the thrills of travel. Click on our "Properties good for families" filter to discover stays loaded with amenities ideal for travelling families, like dining rooms, pools, bunk beds and hot tubs.

Q: What are the top attractions for families in Chesapeake Beach?

Keeping the kids occupied during your stay in Chesapeake Beach is a snap with these leading family-friendly attractions: Breezy Point Beach Chesapeake Beach Water Park Bayside History Museum

Q: Can I find two-bedroom holiday rentals in Chesapeake Beach?

Gather your family and relax in total privacy and comfort in one of the four two-bedroom holiday rentals Chesapeake Beach has to offer.

Q: Are there holiday rentals with WiFi in Chesapeake Beach?

Chesapeake Beach has two holiday rentals with WiFi, so you can stay connected during your holiday. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming Hollywood blockbusters to writing and sending emails, these Vrbo homes make it easy to get online.

We found holiday rentals — enter your dates for availability

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Dates

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May 2025

June 2025

Discover a selection of 9 homes and other holiday rentals in Chesapeake Beach that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll have the amenities that you expect and more, which might include parking and a fireplace. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Chesapeake Beach

Showing deals for:25 Jul - 1 Aug

Exceptional

(33 reviews)

Annapolis Area Private, 3 Bedroom Pool, Jacuzzi & Sauna & Casino-Like Game Room

Davidsonville, MD

6% off

S$1,629 per night

includes taxes & fees

spacious and comfortable living room, with table/six chairs at far end

Exceptional

(23 reviews)

Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!

Annapolis, MD

7% off

S$2,724 per night

includes taxes & fees

Sit on the patio and enjoy your coffee in the morning.

Exceptional

(19 reviews)

Stunning Water Front Home with Private Dock and Beach and Sunsets

Lusby, MD

8% off

S$966 per night

includes taxes & fees

Exceptional

(14 reviews)

Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

St. Leonard, MD

8% off

S$433 per night

includes taxes & fees

Single Family Home With Parking for two small or one larger vehicle.

Exceptional

(59 reviews)

Recently Renovated Annapolis Home - Conveniently Located

Annapolis, MD

8% off

S$778 per night

includes taxes & fees

Exceptional

(15 reviews)

West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis

Annapolis, MD

12% off

S$433 per night

includes taxes & fees

Exceptional

(7 reviews)

Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock

Annapolis, MD

8% off

S$2,049 per night

includes taxes & fees

Exceptional

(9 reviews)

Charming Home located minutes from the Naval Academy and Downtown Annapolis

Annapolis, MD

8% off

S$799 per night

includes taxes & fees

Exceptional

(192 reviews)

Waterfront Log Cabin with Million Dollar View & Luxury Bath! Shark's Teeth!

Port Republic, MD

8% off

S$475 per night

includes taxes & fees

Koi pond, babbling brook and outdoor dining area.

Exceptional

(92 reviews)

Adjacent to Annapolis~ by beach, 25 acre park next door & TV shows filmed here!

Edgewater, MD

8% off

S$664 per night

includes taxes & fees

Wonderful

(33 reviews)

Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis

Annapolis, MD

8% off

S$295 per night

includes taxes & fees

Exceptional

(89 reviews)

Spacious house, great deck & grill, close to boardwalk, shops, and restaurants.

North Beach, MD

8% off

S$388 per night

includes taxes & fees

Exceptional

(34 reviews)

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

West River, MD

12% off

S$241 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Chesapeake Beach

Chesapeake Beach Water Park

Find the best place to stay - Chesapeake Beach

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Sleeps 8 · 4 bedrooms · 2 bathrooms

Mid-Century Modern on Private Beach, Designed by Award Winning Architect!

Sleeps 5 · 2 bedrooms · 1 bathroom

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

Explore the beachside setting in Chesapeake Beach

Enjoy the live music and other features of Chesapeake Beach. This relaxing and romantic city is well known for its restaurants, spas and beaches. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Chesapeake Beach

Are you hoping to find attractions to see during your stay? Venture out of your holiday home and experience everything that makes Chesapeake Beach a one-of-a-kind holiday spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

Chesapeake Beach Water Park (0.2 mi / 0.3 km)
Fridays Creek Winery (7.6 mi / 12.2 km)
Running Hare Vineyard (13.6 mi / 21.9 km)
Lake Presidential Golf Club (14.9 mi / 24 km)
South River Golf Links (15.7 mi / 25.2 km)
Renditions Golf Club (16.5 mi / 26.6 km)

Exploring the natural features in Chesapeake Beach

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Chesapeake Beach is a great spot to appreciate mother nature. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

Upper Yough River (4.6 mi / 7.4 km)
Breezy Point Beach (5.2 mi / 8.3 km)
Shadyside Park (10.6 mi / 17 km)
Triton Beach (13.3 mi / 21.3 km)
Battle Creek Cypress Swamp Sanctuary (14.4 mi / 23.1 km)
Matoaka Beach (15.7 mi / 25.3 km)

Seasonal weather averages in Chesapeake Beach

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 24°C.

How to get to and around Chesapeake Beach

Fly into Easton, MD (ESN-Easton - Newnam), the closest airport, located 26.5 mi (42.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into College Park, MD (CGS), which is 28.8 mi (46.3 km) away.

Frequently asked questions

What is the most popular type of holiday rental accommodation in Chesapeake Beach?

Based on our research, houses are the most sought-after holiday property type in Chesapeake Beach. But as you might expect, everyone’s idea of an awesome stay is bound to be different. Vrbo has holiday homes with every shape, size and budget in mind, so you’re sure to discover your ideal match.

How much does it cost to rent a holiday rental in Chesapeake Beach?

Several things influence how much you pay for a holiday rental in Chesapeake Beach, like the length of stay, season and type of property. But, all of our holiday homes have something in common — excellent value. Just add your travel dates to find your ideal escape.

How much does it cost to rent a beach house in Chesapeake Beach?

The average price for a holiday rental near the beach in Chesapeake Beach depends on when you’re going and the style and size of property you’re searching for. You can easily find prices on Vrbo by entering your preferred travel dates. Then use the handy filter tool to choose the number of bedrooms and amenities important to you, such as air conditioning, WiFi and a hot tub.

Are there pet-friendly holiday rentals in Chesapeake Beach?

Yes. There are. You can choose from seven holiday rentals that allow pets in Chesapeake Beach. Plenty of our pet-friendly holiday rentals even have a garden for your four-legged fur baby to run around in, dog beds, complimentary treats and proximity to parks and green space. Apply the “Pets allowed” filter to find your pawfect pad on Vrbo.

What are popular rental amenities in Chesapeake Beach?

When it comes to rental amenities that guests are looking for in Chesapeake Beach, a nearby waterfront, nearby museums and a water view are at the top of the list. With Vrbo holiday homes, there are options to match your style and taste, whether you’re going on a holiday with family, friends or even pets.

Are there large group holiday rentals in Chesapeake Beach?

With six Chesapeake Beach holiday homes that can accommodate five or more people, you can invite a few extra pals or family members along. Whether you’re planning an informal get-together or a special event, we’ll help you find a comfy space to match the occasion.

Are there holiday rentals in Chesapeake Beach that welcome kids?

With seven family-friendly holiday properties to pick from in Chesapeake Beach, now is a fantastic time to introduce your children to the thrills of travel. Click on our “Properties good for families” filter to discover stays loaded with amenities ideal for travelling families, like dining rooms, pools, bunk beds and hot tubs.

What are the top attractions for families in Chesapeake Beach?

Keeping the kids occupied during your stay in Chesapeake Beach is a snap with these leading family-friendly attractions:

Breezy Point Beach
Chesapeake Beach Water Park
Bayside History Museum

Can I find two-bedroom holiday rentals in Chesapeake Beach?

Gather your family and relax in total privacy and comfort in one of the four two-bedroom holiday rentals Chesapeake Beach has to offer.

Are there holiday rentals with WiFi in Chesapeake Beach?

Chesapeake Beach has two holiday rentals with WiFi, so you can stay connected during your holiday. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming Hollywood blockbusters to writing and sending emails, these Vrbo homes make it easy to get online.

How can I find holiday rentals with air conditioning in Chesapeake Beach?

Chesapeake Beach has seven holiday rentals where you can relax in air-conditioned comfort. To book a stay on Vrbo that has this amenity, enter your dates of travel and use the convenient filters to select the “air conditioning” box.

How old do you have to be to rent a holiday rental in Chesapeake Beach?

The minimum required age is normally 16, 18 or 21. It can vary between properties on Vrbo, so check the rules of your preferred Chesapeake Beach holiday rental before making a booking.

How long can I rent a holiday rental in Chesapeake Beach for?

It all depends on the Chesapeake Beach property. To browse available options offering extended stays, just type your travel dates and number of people into Vrbo. You can look forward to having the entire property to yourself, along with home comforts such as a full kitchen, air conditioning and outdoor spaces where your little ones can play. Keep your eyes open for any long-term stays that offer weekly or monthly discounts.