Eastern Shore Vacation Rentals

We offer a wide variety of Eastern Shore vacation rentals in Maryland from St Michaels to Oxford and everywhere in between. Below you will find different rentals by category based on location or your desired amenities. You can choose vacation rentals that are great for large groups, rentals that have a pool and/or central air conditioning, we truly have something for everyone! Start exploring today, we can't wait to help you find the perfect Maryland vacation rental!

Browse & Book Direct

It Pays to Book Direct! You have searched the travel websites. You have narrowed down your options and found your favorite rental property. You are ready to book. STOP RIGHT THERE! Booking through a travel website costs you more! Airbnb, VRBO, HomeAway, TripAdvisor, and others add significant fees when you book through them. Same for many online travel agencies. You can avoid these fees and save big by booking directly through ESVR. Theres no markup, and you can easily communicate any special needs or requests. Browse a Bigger Selection Heres another trick of the trade: If you browse through ESVR first, youll see every property we offer. Thats not always true with travel websites. Those sites dont list all vacation rentals because these listings are expensive for property owners. Along the North Carolina coast, for example, only 30% of all rental properties are listed on the major sites. That means you miss out. ESVR also has special offers, flash sales and off-season discounts that the major travel sites dont always list. Get the Inside Scoop Finally, the ESVR team can always give you the most updated information on our rentals and community. We tell you about new amenities, lesser-known area events, the best restaurants, and hidden gems. Book smarter, and book directly through ESVR. Youll save on your vacation and have a much better experience.

St. Michaels

These vacation homes are all convenient to historic St. Michaels, Maryland to enjoy dining, shopping, and sight-seeing. Please note prices given below are per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Less than weekly stays are typically a higher nightly rate and prices will vary based upon season and number of nights booked. For an exact quote, please input your dates on the property page.

Oxford

Enjoy the quiet nautical ambiance of Oxford, Maryland by renting one of our village cottages or estate homes on the outskirts of town. Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

Annapolis

Introducing our newest location, Annapolis, Maryland! Soak in all the charm that historic Annapolis has to offer for a weekend getaway or Naval Academy events. We are in the process of adding new properties in time for your Summer 2019 vacation, so please be sure to check back here often for the newest homes.

Cambridge

Enjoy a weekend in Cambridge, Maryland exploring the Blackwater National Refuge, enjoying local dining and shops or just relaxing and enjoying the big wide water views! Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

Chestertown

ESVR is now cultivating a portfolio of fine homes in the Chestertown area! Perfect for our guests coming from the Philadelphia area or for those that just want to try a new area, these properties offer privacy and the chance to explore the charming and quaint town of Chestertown, Maryland. More properties coming soon, book your Chestertown MD rental today! Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

Pet-Friendly

Whats a vacation without your best friend? These properties are pet-friendly for dogs (two dog limit!). As always, there are no additional pet fees! Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

Tilghman

Looking for an "away from it all" vacation? Tilghman Island is a great option when you want an unspoiled and authentic vacation experience. Off the beaten path but close enough to St. Michaels to enjoy restaurants, shopping and sightseeing. There are a variety of waterfront cottages and vacation homes available in Tilghman Island, browse and book online today! Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

Homes with Pools

There is nothing like having your own refreshing private pool to cool off after a fun day on the water fishing, crabbing, or just sightseeing. Perfect for larger groups, many of these homes come complete with lounging and patio furniture as well as grilling tools for the perfect backyard hangout! Our swimming pools are open from May 15-October 15. Some homes do offer pool heat at an additional charge; please inquire for more details. Also, note that the early and late parts of the season may affect water temperatures, however, pools are open to maintain the ambiance of the property. Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

Luxury Homes

Looking for more than just the comforts of home? These properties offer luxuries not found in your typical vacation rental home, such as private swimming pool, dock, multiple acres, high-end kitchens or amazing outdoor spaces. Feel free to browse these fantastic properties! Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

Multi Family Homes

If your idea of a vacation is reconnecting with loved ones or special friends, these properties provide just the ticket! Our larger homes sleep 10+ (please note in Talbot County 12 is the absolute maximum occupancy) and have amenities for all ages to enjoy. From refreshing swimming pools to private docks for fishing, kayaks, bikes and much more. Check out the selection of our multi-family vacation homes in the Chesapeake Bay area and please inquire about a specific homes amenities before booking. Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.

View All Properties

Check out the category groups below to find your next Eastern Shore vacation rental in Maryland! Located in and around the St Michaels area, our vacation rentals offer great opportunities for exploring, adventure and relaxing. Enjoy breathtaking scenic views of the ocean and bay, hot tubs, fire pits, and beautifully cared for properties. Guests often take advantage of nearby fishing and crabbing holes as well as the area beaches and attractions. Whether you are looking to get outdoors, see the nearby towns, or spend the days on the sand, we offer a wide variety of rentals with great amenities and features. Please note prices below per night, based on the summer weekly price for seven nights and are given as a range to assist you with choosing a property. Nightly prices vary per season and per number of nights booked. For an exact quote, please input your dates on the property page.