On February 20, dog owners across the country celebrated their furry, four-legged friends for National Love Your Pet Day. Now, show your adoration by booking a dog-friendly family vacation for the summer on Maryland’s Eastern Shore. 

Eastern Shore Vacation Rentals (ESVR) has more than 50 fantastic properties, and most of them welcome dogs—with no extra fees! Choose from majestic waterfront estates to quaint historic cottages in charming towns such as Oxford, Cambridge, Annapolis, St. Michaels and Chestertown. 

You’ll love the dazzling sunsets, delicious seafood and slow pace of relaxing days. And your dog will love splashing around at the local beaches and playing fetch in the green, open spaces. 

Maryland’s Eastern Shore is dog country, so you’ll find plenty of places to visit and things to do together.

Tail-wagging fun for all

If you’re heading to the Eastern Shore from the west, take a break at Matapeake Park Dog Beach. It’s your first exit off the Bay Bridge. Set out through the winding woodsy trail that leads to the dog beach on the sandy banks of the Chesapeake. 

Down south a bit in Crisfield, you and your pups can climb into a kayak and explore more than 30 miles of water trails and secluded beaches of Janes Island State Park

In St. Michaels, your dog is welcome aboard the Patriot Boat Cruise, which tours this historic town by water. While you’re there, be sure to check out the dog-friendly Chesapeake Bay Maritime Museum next door. Located along 18 waterfront acres, the museum features a working boatyard where you can see the restoration of traditional Chesapeake Bay vessels. 

If you’re spending time in Oxford, and you should, grab a bite at Capsize, a waterfront locals’ favorite where dogs can get cool water and lounge on the outdoor deck. Snappers Waterfront Café and Tiki Bar in Cambridge keeps you in the vacation mindset with a dog-friendly deck, delicious Maryland lump crab cakes and Caribbean-style cocktails.

Book your dog-friendly Eastern Shore vacation

Do something special for your whole family in the spirit of Love Your Pet Day. Plan a summer vacation on Maryland’s Eastern Shore with a rental from ESVR. 

Remember, dogs are welcome in most ESVR properties—and there are no extra fees for pets!

Book your favorite rental through ESVR today before it’s gone. And be sure to book direct with ESVR to avoid paying extra fees. 

If you want to know more about our rentals or the dog scene on the Shore, contact our friendly reservationists at 410-770-9093 or [email protected].

This Easter, start a new family tradition with a weekend on Maryland’s serene, historic Eastern Shore. 

Grab your basket and hunt for eggs amid breathtaking waterfront vistas. Explore local waterways by kayak and ride bikes into the towns where life moves at a slower pace. When it’s time for your big holiday meal, prepare ham, lamb or a steaming pot of crabs in a kitchen stocked with everything you need. 

Eastern Shore Vacation Rentals has a selection of properties just right for your family or several families. Dogs are welcome, at no extra charge. And all ESVR properties include bed and bath linens, with beds made prior to your arrival. 

Find your favorite and book now for Easter weekend before they’re gone.

Cozy and Charming Homes

Treat your family to the quintessential Eastern Shore experience in one of our quaint cottages. Beautifully appointed and picturesque, each home allows you to feel more connected but never cramped.

Mallard Point Cottage – SOLD OUT!

McDaniel, MD 

4 Bedrooms 3 Baths Sleeps 8

Share laughs and stories together on Mallard Point’s large screened-in porch looking out to the water. Feel the stress melt away with coffee or cocktails on your private dock. And spend evenings snuggled up with a book or watching movies by the crackling fire.

Caulk’s Cove

Bozman, MD

3 Bedrooms 2.5 Baths Sleeps 6

Find total relaxation just outside the historic water town of St. Michaels. Caulk’s Cove is a secluded paradise with everything your family needs to make a memorable Easter, including a deep-water pier and an outdoor fire pit. Toasted Peeps, anyone?

Pride and Joy

Oxford, MD

3 Bedrooms 2 Baths Sleeps 6

The brick walkway, lush landscaping, white picket fence and screened porch tell you all you need to know about this gorgeous cottage. It’s a slice of small-town Americana, decorated with bright colors throughout and furnished for comfort. You’re just a short walk from Oxford’s parks and unique restaurants.

Multi-Family Rentals

When it comes to the holidays, the more the merrier. These sprawling estates have more than enough room for your extended family or several other families to join the Easter festivities.

Willoughby – SOLD OUT!

Cambridge, MD

7 Bedrooms 6 Baths Sleeps 24

This retreat on the Hudson Creek waterfront redefines the term living large. The inside includes more than 10,000 square feet of luxurious amenities and furnishings you have to see to appreciate. The heated indoor pool and screened-in hot tub are both open for use year-round.

Belle Aire Landing

East New Market, MD

9 Bedrooms 6 Baths Sleeps 22

A private beach on the Choptank River. A dance hall converted into a guest house. Waterfront dining. A waterside crab house. Exquisite furnishings and details throughout. This compound near Cambridge has all you could ever want and need for an incomparable Easter holiday.

Time to explore

You may not wish to leave your rental property, but if you do, Maryland’s Eastern Shore has a bounty of attractions for families. 

In Cambridge, the Harriet Tubman Underground Railroad Visitor Center and State Park gives you a close look at the incredible life and brave deeds of a true American hero.  

Kids of all ages love the Chesapeake Bay Maritime Museum in St. Michaels, where you can tour a working shipyard, see a lighthouse from 1879, join the crew of an oyster harvesting skipjack and try your luck harvesting crabs and other seafood. If you come down to celebrate Easter a week early, be sure to visit the 9th Annual Eastern Shore Sea Glass and Coastal Arts Festival on April 4 and 5. 

Easter weekend is nearly a month into spring, so take advantage of favorable April weather with a trip to the Blackwater National Wildlife Refuge. There’s a guided birding tour on Saturday, April 11, where you’ll have a chance to see bald eagles and several species of waterfowl.

Plan your new Easter tradition with ESVR

Pack up your baskets, bonnets and chocolate bunnies this Easter and treat your family to an unforgettable holiday on Maryland’s Eastern Shore. 

Whether you need to accommodate one family or five, ESVR has the home to make your trip special. Find and book your favorite rental through ESVR to avoid extra fees. If you have any questions about Easter weekend or anything else, reach out to our reservations team at 410-770-9093 or [email protected].