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.

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.

Waterfowl Festival

The Eastern Shores signature annual event, the Waterfowl Festival is an event packed family weekend for celebrating all things Eastern Shore--food, fowl and fun! For more information, visit www.waterfowlfestival.org

Fall Cottage Getaways

Looking for a great fall getaway? These 2-3 bedroom cottages are available for a minimum of two nights after Labor Day and include complimentary early arrival and late departure (if available), as well as all other fees, bed and bath linens and pet fees (if home if pet friendly). Make plans now to be on the Eastern Shore for the best season of all! 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!

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.

Last Minute Weekly Deals

**LAST MINUTE DEALS REMAINDER OF JULY** Save 15% now on a 3+ night stay when you book these properties for either last minute arrival or on select discounted weeks! These deals are offered on a first come, first served basis. Must confirm at time of reservation with a deposit, no holds for last minute deals. Offer not valid with other offers. Participating properties only. Not valid for existing reservations.

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.

Labor Day Weekend

We hate to see summer go! Make it stretch a little longer with one last hurrah on MDs Eastern Shore! The crabs will be plentiful and you will have memories to linger until next season! 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.

Summer Cottage Getaways

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!

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.

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.

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.

Thanksgiving on the Shore

Thanksgiving is a special time to visit MDs Eastern Shore--beautiful colors, waterfowl migrating above, succulent seafood (oysters!!) and local cuisine all set a perfect backdrop for a treasured family celebration. There is a 3 night minimum stay requirement for the Thanksgiving holiday weekend. 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.