Eastern Shore Vacation Rentals

St. Michaels

These vacation homes are all convenient to historic St. Michaels 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 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 ambience of Oxford, MD 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. More properties coming soon!

Tilghman Island

Looking for an "away from it all" vacation? Tilghman Island is a great option when you want an unspoiled and authentic experience, but close enough to St. Michaels to enjoy restaurants, shopping and sightseeing. There are waterfront cottages and vacation homes available in Tilghman Island. 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--refreshing swimming pools, private docks for fishing, kayaks, bikes and more. Please inquire about a specific homes amenities before booking.

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 pool to cool off after a fun day on the water fishing, crabbing, or just sight seeing. Our swimming pools are open from May 15-October 15. Some homes do offer pool heat at an additional charge. Please inquire. Also note that the early and late parts of the season may affect water temperatures, however, pools are open to maintain the ambience 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.

Last Minute Deals

Looking for a great last-minute deal for the upcoming weekend? Book a 2+ night stay in a participating property within two weeks of arrival and save 20%!

View All Properties

Feel free to browse our great selection of cottages, waterfront homes and estates. We would be happy to help you find just the right spot for your vacation! 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 cottage 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.

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!