Specializing In Short-Term Vacation Rentals For More Than 15 Years.

specializing in short-term vacation rentals on Maryland's Eastern Shore for more than 15 years.

Discover the potential of your Chesapeake Bay rental investment
Pool*
Waterfront
Discover the potential of your Chesapeake Bay rental investment
Pool*
Waterfront

Eastern Shore Vacation Rentals is ready to manage your short-term Vacation rental and maximize Your return on investment. It's All We Do!

Our focus and reputation allow us to welcome more than 6,000 vacation home renters each year, based on delivering services and experiences not just unique to Maryland’s Eastern Shore, but the vacation rental industry. We carefully manage your property before, during and after your guest’s experience, so you don’t have to.

A Partner You can trust

Homeowner Services

Short-Term Licensing and Permitting

Our team will walk you through the process of applying for and/or renewing your short-term rental license. We will also act as your resident agent at the licensing hearings and with any licensing issues.

Transparent Owner Communication

Stay connected with your property through our online owner portal that allows you to access your booking calendar, owner statements, and maintenance history. We NEVER put a limit on owner stays.

State and Local Taxes

We handle sales tax reporting for you! Don’t second guess your financial reporting or pay penalties for an incorrect filing.

Quality Guests

Through guest vetting and our rental agreement, we identify the names and ages of every guest, enforce a strict no event policy and only rent to people we feel are going to respect your property.

No Nickel & Diming

Our management fee covers all basic maintenance like light bulbs and batteries. If third party services are needed, you can rest assured that we NEVER markup vendor invoices.

Local Property Management

We manage any issues that may arise during a guest’s stay, make sure houses are clean and ready for owner stays and inspect properties annually.

Homeowner Services

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Short Term Licensing and Permitting

Our team will walk you through the process of applying for and/or renewing your short-term rental license. We will also act as your resident agent at the licensing hearings and with any licensing issues.

Image

Transparent Owner Communication

Stay connected with your property through our online owner portal that allows you to access your booking calendar, owner statements, and maintenance history. We NEVER put a limit on owner stays.

Image

State and Local Taxes

We handle sales tax reporting for you! Don’t second guess your financial reporting or pay penalties for an incorrect filing.

Image

Quality Guests

Through guest vetting and our rental agreement, we identify the names and ages of every guest, enforce a strict no-event policy and only rent to people we feel are going to respect your property.

Image

No Nickel & Diming

Our management fee covers all basic maintenance like light bulbs and batteries. If third party services are needed, you can rest assured that we NEVER markup vendor invoices.

Image

Local Property Management

We manage any issues that may arise during a guest’s stay, make sure houses are clean and ready for owner stays, and inspect properties annually.

Innovative Marketing

Eastern Shore Vacation Rentals innovative, aggressive and comprehensive marketing strategies go to work for our homeowners to maximize bookings.


We offer the latest in technology including dynamic revenue management, easy to use website, the most popular third party booking channels, and social media networks to get homeowners the maximum return for their investment.

Cutting Edge Revenue Management

We invest in Beyond Pricing, which acts to dynamically change rental rates to match supply and demand. This tool strategically adjusts rates to maximize your listing’s revenue and occupancy.

Extensive Guest Database

With a database of more than 25,000 vacation home renters, the majority of our reservations come from repeat guests.

Online Marketing

Eastern Shore Vacation Rentals has a top ranking status on third party vacation rental sites and invests heavily in digital advertising so we are consistently at the top of search engine rankings.

Property Management

The care and maintenance of your investment is your top priority. Our thorough inspections, 24/7 emergency response team and strong vendor relationships will ensure your guests have a positive rental experience in your well-maintained property.

Thorough Inspections

We thoroughly inspect every home prior to a guest’s arrival and after each departure. Our properties undergo comprehensive pre and post season inspections and provide feedback regarding any maintenance concerns.

24/7 Emergency Response Team

Even the most well-maintained home has unexpected failures or problems. We stand ready to respond to these issues immediately so we can keep your guest’s vacation on track.

Strong Vendor Relationships

With a reliable and professional network of vendors, we will coordinate and dispatch a provider to respond quickly–be it an HVAC failure, swimming pool problem or appliance in need of repair.

Innovative Marketing

Eastern Shore Vacation Rentals' innovative, aggressive and comprehensive marketing strategies go to work for our homeowners to maximize bookings.


We offer the latest in technology including dynamic revenue management, an easy-to-use website, the most popular third party booking channels, and social media networks to get homeowners the maximum return for their investment.

Image

Cutting Edge Revenue Management

We invest in Beyond Pricing, which acts to dynamically change rental rates to match supply and demand. This tool strategically adjusts rates to maximize your listing’s revenue and occupancy.

Image

Extensive Guest Database

With a database of more than 25,000 vacation home renters, the majority of our reservations come from repeat guests.

Image

Online Marketing

Eastern Shore Vacation Rentals has a top ranking status on third party vacation rental sites and invests heavily in digital advertising so we are consistently at the top of search engine rankings.

Find out what your home is worth.

What Our Owners Have To Say...

Learn more about our vacation rental program

Property Management

The care and maintenance of your investment is your top priority. Our thorough inspections, 24/7 emergency response team, and strong vendor relationships will ensure your guests have a positive rental experience in your well-maintained property.

Image

Thorough Inspections

We thoroughly inspect every home prior to a guest’s arrival and after each departure. Our properties undergo comprehensive pre and post-season inspections and provide feedback regarding any maintenance concerns.

Image

24/7 Emergency Response Team

Even the most well-maintained home has unexpected failures or problems. We stand ready to respond to these issues immediately so we can keep your guest’s vacation on track.

Image

Strong Vendor Relationships

With a reliable and professional network of vendors, we will coordinate and dispatch a provider to respond quickly–be it an HVAC failure, swimming pool problem, or appliance in need of repair.

Guest Services

Today’s vacation rental guests want more than just a place to stay. It’s not enough anymore to just deliver a clean and well-maintained home. Guests expect a high-level of customer service before, during and after their stay.

Personalized Guest Services

Each guest will be assigned a dedicated member of our guest service team who stands ready to answer questions about your property as well as find activities and amenities to make their stay a memorable one.

Guest Portal

Eastern Shore Vacation Rentals guest’s receive automatic checkpoints throughout their stay. Our guest portal allows them to manage reservations, pay balances, sign rental agreements and select add-on services all in one place!

24/7 Support

Rest easy knowing your guest’s have continuous support from our local team of experts. We’re available 24/7 to assist guests.

Guest Services

Today’s vacation rental guests want more than just a place to stay. It’s not enough anymore to just deliver a clean and well-maintained home. Guests expect a high level of customer service before, during, and after their stay.

Image

Personalized Guest Services

Each guest will be assigned a dedicated member of our guest service team who stands ready to answer questions about your property as well as find activities and amenities to make their stay a memorable one.

Image

Guest Portal

Eastern Shore Vacation Rentals guests receive automatic checkpoints throughout their stay. Our guest portal allows them to manage reservations, pay balances, sign rental agreements, and select add-on services all in one place!

Image

24/7 Support

Rest easy knowing your guests have continuous support from our local team of experts. We’re available 24/7 to assist guests.

Join the Eastern Shore Vacation Rentals family today!

We carefully manage your property before, during and after your guest’s experience, so you don’t have to.

We carefully manage your property,

so you don’t have to.

719 Goldsborough Street

Easton, Maryland 21601

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