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.

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.

Annapolis Properties--Coming Soon!

Great News! Eastern Shore Vacations is heading to the Western Shore! Check back with us soon for some awesome homes to enjoy in the Annapolis area! Have a property that you are interested in renting? Give us a call at 410-770-9093 or e-mail us at [email protected] to speak with our Annapolis Properties Representative.

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!

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.

Hunting Properties

Properties that allow hunting on premises with a professional guide. Check back frequently for more properties added for the 2017-2018 hunting season.

New Years Eve Properties

Theres a new year on the horizon, and what better way to start 2018 than with friends and family in a cottage on MDs Eastern Shore? There is still time to book a waterfront home, an Oxford cottage or large estate property for New Years weekend! No matter how you choose to celebrate--staying in and cooking a gourmet meal, or enjoying an evening out in one of our acclaimed local restaurants, the Eastern Shore is a special place to be when the clock strikes midnight! Kids love the "crab drop" in Easton!

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.

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.

Holiday Specials

Save 15% when you book a participating property and stay between now and the end of the year. A great way to escape the hustle and bustle of the holiday, reconnect with friends and family or get a head start on that Christmas list. Dont forget about First Night Talbot, a fun family oriented event (complete with a crab drop!) for New Years Eve.

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.

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.

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.

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.