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Last Minute Deals

Save 15% when you book within two weeks of arrival! These homes are on special from April 14-April 28 To receive your savings, use code LMD. Offer not valid with other offers. Participating properties only. Not valid for existing reservations.

WineFest at St. Michaels

A not to miss premier international wine tasting event set in our charming town of St. Michaels, WineFest 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

Memorial Day Weekend

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

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!

Flexible Summer 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!

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.

Summer Weekly Rentals Under $2500

Looking for a budget friendly way to enjoy the Eastern Shore? Maybe you just want a more intimate vacation in a smaller cottage, or to explore the area and enjoy all the local trimmings. These properties are a great way to kick the tires on the Eastern Shore Lifestyle, and include all the great amenities our larger homes offer--bed and bath linens, free pets (pet friendly homes) and starter amenities for kitchen and bath. All other fees included except state and local taxes. Travel insurance available at additional cost.

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.