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Memorial Day Weekend

Join us for the unofficial start to summer! Kick off the warm weather with a waterfront home and Chesapeake Bay breezes!

Spring Break Getaways

Trade those winter blues for Chesapeake blues--blue water, blue crabs and blue skies! Spring offers many ways to put winter firmly behind you and look ahead to the sunshine. WineFest, Oxford Day, Easter Weekend, and Memorial Day Weekend are just a few. For all Spring Events, visit our Event section on our website.

Wine Fest at St. Michaels

A not to miss premier international wine tasting event set in our charming town of St. Michaels, Wine Fest is a popular weekend to visit the Eastern Shore to savor wine and local cuisine and catch your first breath of spring! April 29-30, 2017 For more information: winefestatstmichaels.com

St. Michaels Vacation Rentals

These vacation homes are all convenient to historic St. Michaels to enjoy dining, shopping, and sight-seeing 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 Vacation Rentals

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.

Cambridge Vacation Rentals

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 Vacation Rentals

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 Area Vacation Rentals

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!

Weekend Cottages

What could be better than taking a long weekend to catch your breath? Our cottages offer a chance to visit the Eastern Shore for shorter stays year round, and take in all the Eastern Shore has to offer.

Multi Family Vacation 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.

Pet Friendly Vacation Rentals

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.

Vacation Rentals 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.

Luxury Vacation Rentals

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.

Monthly Rentals

Looking for a longer term rental? Many of our properties do offer monthly rentals from October to May. Monthly pricing ranges from $2500-$5000 per month, and do not include housekeeping or linens during your stay. Please inquire for more information regarding our monthly rental program. Monthly rentals are subject to final approval by of the homeowner.

Vacation Rentals with Kayaks/Water Toys Included

For an added value, these properties include one or more kayaks, canoes or paddleboards for your use during your stay. Please consult rental agreement for terms and conditions. For your convenience, there are also several local providers that will deliver water toys to your property with advance notice. 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

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.