Eastern Shore Retreats
Vacation Rental Houses

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---Adjusted rates apply to all units for Pony Penning week---
Please call or email to inquire about rentals that are available during the off season.



Get ready to enjoy an All Decked Out vacation!

All Decked Out is a 4 bedroom, 3 full bath, central air conditioned, waterfront home that sleeps up to ten (10) people with 1 King, 3 Queen,1  Double Futon. Nestled along the Assateague Channel you can enjoy panoramic views of Assateague Island, and the Assateague Lighthouse from almost every room in the house. The expansive balconies offer relaxation and cool salt breezes on even the warmest of days. This home offers an open floor plan, fully furnished kitchen that is a chef's dream, dining room with ample seating, spacious master suite, and much more. We invite you to leave your worries and cares behind, and enjoy an All Decked Out Vacation.
Assateague Overlook #2 is located on the eastside of Chincoteague just off the bank of the Assateague Channel. Enjoy watching the wild ponies from your balcony. Experience the wonderful breezes. Take in the breath taking views of Assateague Island and the historic Lighthouse. You are within a stone's throw of the town boat ramp right across the street and within a couple of blocks of Memorial Park which has a play ground, tennis courts and public pier for fishing & crabbing. It is within walking distance of shops, boat rentals, restaurants, seafood & vegetable stand andmuch more.
Bayberry is an inviting, 2 bedroom, 2 1/2 bath, centrally air conditioned, canal front townhome that sleeps up to 6 people with 1 Queen, 1 Queen sleep sofa, and 2 Twin beds. Enjoy the fresh salt air, beautiful sunsets, and watching wildlife from the first floor deck, or the second floor balcony which has a view of the Chincoteague Channel. If you enjoy being outdoors, you will love crabbing and kayaking the canal from the shared dock. We invite you to come and enjoy a relaxing island vacation at Bayberry.
Bayside Sunset , formerly known as Pine Warbler, is a 2 bedroom, 2 1/2 bath, centrally air conditioned townhome that sleeps up to six (6) people with 1 Queen, 2 Twins, and 1 Queen Sleeper Sofa. Located along the banks of a canal, this home offers wetland water views, and a shared crabbing pier. Breathtaking Bayside Sunsets await you and your guests at this inviting island retreat.
Beacon View is a beautiful 4 bedroom, 3 full bathroom home located on the deep water of Assateague Channel, that sleeps up to eleven people. This vacationer's dream has a gorgeous view of Assateague Island and the Lighthouse and includes a private deep water boat dock for fishing, crabbing or just relaxing and enjoying the breathtaking sunrises. You may even catch a view of the ponies as they graze on the salt marsh of Assateague Island. Come and enjoy this vacation getaway and all that the islands have to offer.
Brittany is a spacious waterfront home on one acre with 3 bedrooms, 3 1/2 baths, central air, a private dock, a large backyard, and beautiful views of the sunrise.  It sleeps up to 12 people.  Enjoy bird watching, crabbing, sunbathing, family cook outs, and stargazing right off the backyard.  
 
Coastal Haven is coastal living at its finest. Located within easy walking distance to the "Historic Town Of Chincoteague", you will find this 3 bedroom, 2 full bath, centrally air conditioned, Sunset Bay Villa that sleeps up to 6 people with 3 Queen Beds. Enjoy evenings by the pool, strolling thru town, or relaxing in this spacious villa. Relax and unwind at this breath taking "Coastal Retreat".

Coco Banana! Go bananas for this Charming Island Retreat! Be one of the first guests to stay in this newly built home. Conveniently located near the heart of town, this 2 bedroom, 2 full bath, central air conditioned home, sleeps up to 7 people with 2 queen and 2 double futons. This homes tropical feeling is ap - peeling!

Distant View is a 2 bedroom, 1 bath, centrally air conditioned, pet friendly, water view home, nestled along Main Street. This "Chincoteague Style" home sleeps up to 4 people with 1 king, and 2 twin beds. Distant View offers you and your family the slower pace of island life, a step back in time, and beautiful sunsets over the Chincoteague Channel. We invite you to come and enjoy your "Island Vacation", and to leave your worries and cares in the Distant View.
Eagle's View is a 4 bedroom, 3 1/2 bath, centrally air conditioned, Waterfront home that sleeps up to 11 people with 2 queen, 1 double, 1 single, and 4 twin beds, and is the perfect location for the nature lovers in your family.  Wake up to beautiful sunrises, and spend lazy summer days enjoying the many kinds of birds, the frequent views of the ponies, and of course the gorgeous view of the lighthouse. Enjoy fishing, crabbing or boating from the private lighted dock that is also the perfect place for stargazing. There are plenty of outdoor living areas for family gatherings, curling up with a good book, or enjoying the cool, salt air breezes. Come and enjoy the relaxation, peacefulness and tranquility that can be found at this gorgeous waterfront home.  Beautiful sunrises, nature, and relaxation await you at Eagle's View.

Gingoteague, "Beautiful Land Across the Water", is a 2 bedroom, one bath, central air conditioned home nestled in the heart of Chincoteague, within walking distance of Maddox Blvd. and Main Street that sleeps up to 4 people with 1 Queen & 1 Full Bed. This beautifully decorated, newly remodeled, and comfortably furnished home offers large shaded back yard with fire pit, sunroom, spacious kitchen, and much more. We invite you to explore, and enjoy this beautiful land across the water at Gingoteague.

The Half Shell is a bright and airy family retreat nestled in a quiet neighborhood with a large yard, 3 bedrooms, 1 1/2 baths, outdoor hot/cold shower, central air, and is located just a few minutes away from a town dock with easy access for kayaking, canoeing, and boating. The Half Shell sleeps up to 8 people with 1 Queen, 1 Double, 2 Twin (bunk beds), and a Queen Futon. The Half Shell is a peaceful place for you to call home as you explore the beauties of Chincoteague and Assateague Islands.
Homeport is a comfortable, inviting, 2 bedroom, 1 bathroom, centrally air conditioned home that sleeps up to 6 people with 1 Queen , 2 Twin, & one Queen Sleeper Sofa. This home is located on a quiet street within a short walk to town for shopping, dining, and much more. Enjoy spending time on the back deck, screened porch, or in the nice sized yard. We invite you to come and enjoy a memorable vacation, and to make this your island Homeport.

"The Honeymooner" is a charming, 1 bedroom, 1 bath, centrally air conditioned, waterfront home that sleeps up to 2 people with 1 King Bed. The Beautiful unobstructed view of the waterfront, sunsets, and the moon shining over the water makes this the perfect location for a Romantic Honeymoon, or Couples Getaway. Newly remodeled, and beautifully decorated, this home is sure to be the perfect location for your Island Vacation. We invite you and your sweetheart to come and enjoy your stay at "The Honeymooner".

Island Time is an relaxing and inviting 3 bedroom, 2 full bath, central air conditioned home, that sleeps up to 6 people with 1 Queen, 1 Double, and 2 Twin Beds, and is centrally located for easy walks or bike rides to gift shops, ice cream parlors, restaurants, and the Robert Reed Downtown Park located along Main Street. We invite you to spend your week at this charming Island Retreat, and set your clocks to Island Time.
Joshua B. Jones Homeplace is a historic waterman's 19th century Victorian home.  The home  has been newly renovated but still has the beauty and charm of the original home. The home is located on Main Street and is within walking distance of  of town to visit restaurants, movie theater and all the quaint craft and antique shops of Chincoteague Island.
Joy's House is a Charming, 2 bedroom, 2 1/2 bath, Chincoteague Style, waterfront home with stunning views of the Chincoteague Channel. This home is warm and welcoming, and will sleep up to 6 people with 1 king, and 4 twin beds. Enjoy crabbing or fishing just across the street, or unwind from a busy day on the screened porch with a refreshing glass of ice tea. Gorgeous sunsets are included! This home is located close to the Curtis Merritt Harbor. We invite you to come and spend a memorable Chincoteague Island Vacation at Joy's House.

Keeping It Simple is a whimsical three bedroom, 2 full bath, window air conditioned, double wide home that sleeps up to eight people with 3 Double Beds & Queen Sofa bed, and is close to the Curtis Merritt Harbor for the boater in the family.  We invite you to sit back and relax in the screen porch while watching the wildlife & listening to the birds sing, and to make this your next Chincoteague Island Retreat.

Experience the simple, natural and true beauty of Chincoteague Island and Assateague National Seashore from our charming restored vintage cottage.  Central air conditioning, 2 bedrooms, 1 sleeping den with door for privacy, 2 full baths, and sleeps 7 people with 1 Queen, 2 Twin, 1 Twin Trundle Bed, and a Double Futon Sofa. If you need to work from home, internet is provided for your convenience. We invite you to enjoy the simple beauties of the islands, and an enjoyable vacation at this charming vintage cottage.
Las Brisas is a 1 bedroom, window air conditioned, waterfront condo, located on Marsh Island that sleeps up to 4 people with 1 queen bed, and a full size sleeper sofa. You can enjoy crabbing, fishing and docking your boat at this is private "Island Retreat". Enjoy Spectacular sunsets overlooking the Chincoteague Channel from the deck, or while relaxing on the sofa. Beautiful views, relaxation, and cool, salt air breezes are awaiting you at Las Brisas.
Leah's House is a 2 bedroom, 1 Full bath, central air conditioned, newly updated, pet friendly home with large fenced yard and screened patio, that sleeps up to 8 people, and is located within easy walking distance to Memorial Park and the Carnival Grounds.  We invite you to come and enjoy long summer evenings, and a memorable Chincoteague Island Vacation at Leah's House.
Located along the waterfront of Main Street, you will find Lorna's Dune.  A charming Chincoteague Style home, with 2 bedrooms, 1 1/2 baths, dining room, living room, kitchen, central air conditioning, and an enclosed front porch that is perfect for watching the sun set over the water. This home sleeps 4 people with 1 Queen and 2 Twin beds. We invite you to enjoy your next vacation at this Charming Island Home!

Melva's Place a warm and inviting, 2 bedroom, 1 bath, central air conditioned home, located in the heart of Chincoteague, that sleeps up to 6 people with 1 Double, 2 Twin, and I Queen Sleeper Sofa.  This retreat offers a large back yard and screen porch, and is the perfect place for picnics, reading, or just relaxing. Just short walk away, you can explore Historic Downtown Chincoteague, The Robert Reed Downtown Park, and the many shops, ice cream parlors, restaurants, and activities that the island has to offer. We invite you and your family to make Melva's Place your Chincoteague Island Retreat.
My Tern is a charming traditional island home. It is situated in the downtown  section of Chincoteague Island. It is very convenient to and within walking distance of gift shops, galleries, restaurants, grocery stores, churches, the library, the movie theater, boating, fishing and much more.

The Moorings South is a four bedroom, four bathroom, central air conditioned, luxury style vacation rental that sleeps up to eight people, and is nestled directly on the deep water of the Chincoteague Channel and overlooks the beautiful waters of the Chincoteague Bay. Enjoy breathtaking views of the sunset from the main living/kitchen/dining areas or from the "Gazebo in the sky". This beautiful home is located within easy walking distance of cafes, coffee shops, restaurants, ice cream parlors, parks, historic downtown district, walking trails, and much more. We invite you to make Moorings South your luxurious vacation destination.
Morning Sunshine is a cheerful and sunny 2 bedroom / 1 bathroom single family home nestled on Jester Street near the heart of town. Enjoy evenings walking through town and visiting the many restaurants, unique gift shops, ice cream parlors and much more, or if you choose, spend time enjoying the salt air, island breezes in the screen porch. Sun Shine and blue skies are waiting for you at this charming Island Retreat.

Our Sanctuary is a Canal Front, 2 bedroom, 2 1/2 bath, central air conditioned town home that sleeps up to six (6) people with 1 Queen, 3 Twin, and 1 Queen Sleeper Sofa. Enjoy views of the sunset from the deck or the balcony with views of the Chincoteague Channel, or relax while crabbing or kayaking from the shared dock.   We invite you to come and enjoy some much needed relaxation, and make this your Chincoteague Island Sanctuary.

Oyster Catcher is a spacious, light and airy, 3 bedroom, central air conditioned duplex, with beautiful views of the sunset from the front porch, that sleeps up to eight people with 2 Queen beds, 1 Queen Sleep Sofa, and a Bunk Bed ( 1 Double & 1 Twin).  Located just off of Main Street this home is just a short walk from town, or the nature trails that are located on Chincoteague. We invite you to come and enjoy leisurely evenings in the large screen porch, and to make this your Chincoteague Island Retreat.
Paradise By The Lighthouse is located on the eastside of Chincoteague just off the bank of Assateague Channel. Enjoy watching the wild ponies from your balcony and experience the wonderful breezes and breathe taking views of Assateague Island and the historic Lighthouse. You are within a stone's throw of the town boat ramp right across the street and within a couple of blocks of Memorial Park which has a play ground, tennis courts and public pier for fishing & crabbing. It is within walking distance of shops, boat rentals, restaurants, seafood & vegetable stand and much more. There is off street parking at the house for three vehicles. 

Pelican's Roost is a calm and relaxing, 2 bedroom, 1 1/2 bath town home, located on Chincoteague's East Side with a water view of Assateague Island and the Assateague Island Lighthouse.  Relax and unwind while enjoying the sights and sounds of nature on one of the screen porches, overlooking the Salt Marshes of Assateague Island that are abundant with wildlife. Pelican's Roost has an open floor plan making it easy for gathering and entertaining. We invite you to come and enjoy this Calming Island Retreat!

This home will allow pets (limit 1 dog), please inquire about allowable dog breeds.
Peter's House is situated in the Piney Island area. It is within 1/2 mile of  Maddox Blvd., the road to Assateague Island and the beach. It is very convenient to and within walking distance of shops, restaurants, miniature golf and much more. Recently built, this 2 bedroom/1 bath home is centrally air conditioned and is fully furnished with everything necessary for comfortable leisure living.
Pier Pressure (formerly Graceous Living) On Chincoteague Bay is a luxurious townhome that is on the shore of Chincoteague Bay and the daily sunsets are spectacular. This recently completed townhome is right across the street from the carnival grounds. The Chincoteague channel behind the house affords abundant crabbing from the dock and wildlife observation from the multiple decks. The boat dock/pier provides access to the water & a private pool is one more plus that this home offers.

Rachel's Retreat is Waterfront Relaxation at its finest, with gorgeous views of sunsets, balcony to enjoy the cool salt breezes, and Master Bedroom and living room overlooking the waterfront. This beautiful, 2 bedroom, 2 bath, with private den, central air conditioned villa is conveniently located within walking distance to town, shops, restaurants, ice cream parlor, bakery, Robert Reed Park, the carnival grounds, and much more, and sleeps up to 6 people with 1 King, 1 Queen, and 1 Queen Sleeper Sofa (in den). We invite you and your family to enjoy a memorable Chincoteague Island Vacation at Rachel's Retreat.  If you rent here once, you'll want to come back!


Sand and Sea-renity is a Just Listed, "Brand New", charming, calming,  and relaxing, 4 bedroom, 3 and a half bath, central air conditioned home, that sleeps up to 8 people with 3 queen, and one day bed that can be used as 2 Twins or 1 King. Tucked away on a quiet cul-de-sac in Oyster Bay II, and decorated with the tranquil colors of the sand and sea, this beautiful waterfront home is the perfect location for a peaceful vacation.

Sea 'Scape is a Cozy, Coastal Cottage, located along the East Side of the island, with water views of Assateague Island from the screened porch. This 2 bedroom, 1 bath home, easily sleeps up to 6 people with 1 King bed, 2 Twin beds and 1 Queen Sleeper Sofa. We invite you and your family to breathe in the salt air, and to make Sea 'Scape your next Seaside Retreat.

Shoes Off is an adorable 2 bedroom, 1 1/2 bath, central air conditioned town home located on a cul-de-sac, adjacent to Maddox Blvd., that sleeps up to 5 people with 1 Queen, 2 Twin, and a Childs Chair Bed. Located close to the Assateague Wildlife Refuge, golf courses, restaurants, shopping and much more, this is sure to be the perfect Chincoteague Island Vacation Destination. We invite you and your family to kick your shoes off, and relax at this Adorable Island Retreat.
Your Memorable Island Vacation starts where the Sidewalk Ends. Sidewalk's End is an adorable, 2 bedroom, 1 1/2 bath, central air conditioned cottage located in town for summer evenings spent strolling, shopping, playing miniature golf, exploring the many restaurants, and of course the ice cream parlors. We invite you kick off your shoes, relax, and enjoy spending time with family and friends at Sidewalk's End.

Silver Thatch is a wonderful place to enjoy a Peaceful Island Getaway. Enjoy family gatherings on the spacious deck or curl up with a good book in the screened in living area. Silver Thatch is a beautifully decorated 4 bedroom / 2 bathroom home located close to the Assateague Island National Wildlife Refuge in the "Beach Community" of Piney Island. This home is in a great location for easy bicycling or walking to Assateague Island. Silver Thatch is also within walking distance of many restaurants, unique gift shops, miniature golf courses and much more.
Starfish is a spacious, 3 bedroom, 2 bathroom, central air conditioned, "Chincoteague Style" home that sleeps up to 6 people, located within easy walking distance of town, and is the perfect location for  your next family vacation. Enjoy evening strolls to the many shops, restaurants, ice cream parlors, the carnival grounds and much more. Sandy Beach, blue skies, relaxation, and easy island living is awaiting you at this Chincoteague Island Retreat.

Summer Oasis is an adorable, 2 bedroom, 2 bathroom, centrally air conditioned home conveniently located close to town and Maddox Blvd, that sleeps up to six  people with 2 Queen, and  2 Twin beds ( 1 Queen Bed, 2 Twin, 1 Queen Sleep Sofa). We invite you to come and make this home your Summer Oasis.

Sunset View is a breathtaking 3 bedroom / 2 bathroom Beautiful Island Getaway with open views of the sunset. This Sunset Bay Villa is located near town for easy walking to the unique shops, restaurants, carnival grounds and the beautiful Robert Reed Downtown Park.  Enjoy peaceful evenings together watching the sunset on the deck or by the pool. Come and enjoy your Peaceful Island Getaway!

Tranquility is peacefulness, serenity and relaxation at your fingertips. This calming 3 bedroom, 2 full bath, beautifully decorated, central air conditioned villa, sleeps up to 5 guests with 1 king, 1 Queen bed, and 1 twin bed. Conveniently located within walking distance of downtown, Robert Reed Park, restaurants, gift shops, bakery, ice cream parlor, library, carnival grounds, and much more, Tranquility, is the perfect place to spend a memorable, and enjoyable get away. We invite you to come and enjoy the tranquility and relaxation, of this beautiful Sunset Bay Villa.

The Vermont House is a bright and cheerful, centrally located, 4 bedroom, 2 1/2 bath, central air conditioned home nestled on a large lot with fenced in back yard that sleeps up to 8 people with 1 Queen, 2 Double, and 2 Twin beds.

Located a short distance from one of the Island's popular bike paths, staying at The Vermont House allows bikers the opportunity to easily travel to the beach, shopping, and crabbing locations; while leaving their car parked.


Warner Landing is a new, beautiful and inviting, 2 bedroom, 1 1/2 bath, centrally air conditioned townhome that sleeps up to four (4) people with 1 Queen, 2 Twin, and a Queen Pull Out Sofa. Nestled along the water's edge just off of Main Street and within walking distance of downtown, this is the perfect location for much needed relaxation. Front porch and decks offer a chance to enjoy the salt air breezes, while reading a good book, or just enjoying quality "Island Time". We invite you to make Warner Landing your Chincoteague Island Retreat!
The Wilson House is a 6 bedroom, 2 full bath, centrally air conditioned, spacious, waterfront home, that sleeps up to 12 guests, and is the perfect location for your next family vacation. This home is conveniently located within walking distance of town, and close to the carnival grounds. Inviting, large yard welcomes family and friends for picnics, views of the Chincoteague Bay, or for just sitting out under the stars. Come and enjoy a memorable, Chincoteague Island Vacation, at this warm and inviting island home.

For more information or availability/reservations contact Stephanie Taylor at:

Eastern Shore Retreats
6759A Maddox Blvd.
Chincoteague Island, VA. 23336

Phone: 757-336-1088
Email: Pattjack1@Verizon.net or easternshoreretreats@verizon.net