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!

Last Minute Deals

Looking to get away soon or have a flexible schedule? Check out these last minute deals! Great value for a great price, that is our guarantee at Eastern Shore! #mc_embed_signup{background:#fff; clear:left; font:14px Helvetica,Arial,sans-serif; } /* Add your own MailChimp form style overrides in your site stylesheet or in this style block. We recommend moving this block and the preceding CSS link to the HEAD of your HTML file. */ Subscribe to our e-Deals email list for savings delivered right to your inbox!

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.

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.

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.

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.

Tilghman Island

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.

Luxury Properties

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.

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.

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.

Mini Vacations

Looking for a quick summer getaway? These cottages offer flexible check in/check out days as well as just 3 night minimums all summer long! Prices include same amenities as weekly stays--bed and bath linens, starter amenities, and free pets for pet friendly homes, making it a breeze to stay with us this summer!

Properties 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.

Waterfront Cottages

Relax and unwind in our waterfront cottages for a week or long weekend! A great way to explore the Eastern Shore or spend time with a few friends.

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.

Summer Cottages

Perfect for a long weekend, these summer vacation cottages offer up a relaxing getaway without being bound by 7-night minimum stay requirements. All the same amenities as the larger homes, linens included, no pet fees and other fees included. Browse our selection of Chesapeake Bay vacation rentals and contact us for any questions about amenities. 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.

Girls/Guys Weekends

The Eastern Shore is a great place to reconnect with friends or take a much needed respite with your closest buddies. Shopping, golfing, spas, fabulous dining and local wineries are just a few of the activities waiting to be discovered in our quaint towns. Of course, you may want to simply relax at your waterfront property, lounge by the pool or paddle along the river. The choice is yours!