Eastern Shore Retreats
Vacation Rental Houses

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---Adjusted rates apply to all units for Pony Penning week---
NOT ALL UNITS ARE AVAILABLE DURING THE WINTER MONTHS - PLEASE CALL FOR DETAILS

Click Here to download a brochure of our rental homes.

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.
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.

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.

“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.
Just Ducky is a cheerful and inviting 3 bedroom, 3 full bath, central air conditioned Island home with some water view, a back deck,  spacious yard for playing and grilling, and a  screened porch for enjoying the Island breezes.  It is within easy biking or walking distance to the playground, fishing pier and boat ramp at Memorial Park. This home sleeps up to 6 people with 1 King Bed, 1 Queen Bed, and 2 Twin Beds. We invite you to come and spend a memorable Island vacation at this bright and inviting Island home.

Kokomo is a charming, Original Chincoteague Style cottage, that is  Shabby Chic furnished and decorated, and has central air conditioning, 2 bedrooms, 1 sleeping den with door for privacy, 2 full baths, and sleeps up to 6 people with 1 Queen, I twin, 1 Twin Trundle, and a Double Futon Sofa . This home is located within easy walking distance of Maddox Blvd., Historic Downtown, restaurants, movie theater, ice cream parlors and much more. We would like to invite you and your family to enjoy a memorable Chincoteague Island Vacation at this charming Island Retreat.
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. 
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 Pleasure is a centrally air conditioned, two – story, three bedroom, 2 1/2 bath, waterfront duplex on the Eastern Side of Chincoteague Island on Assateague Channel, that sleeps up to 6 people. This home has expansive views of the Chincoteague National Wildlife Refuge at Assateague Island. On most days you can view distant grazing ponies while overlooking Assateague Channel and Horse Marsh. One hundred fifty yards of natural salt marsh between Pier Pleasure and Assateague Channel provide natural cover and nesting areas for birds, turtles, crabs, fish and waterfowl. We invite you to come and enjoy the sights and sounds of nature at Pier Pleasure.

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!

Sail Away to this fun, and happy Island Retreat. This 3 bedroom, 2 1/2 bath, central air conditioned duplex is the perfect location for your next family vacation. Spend long summer afternoons and evenings by the pool, swimming at the beach, or gathering with family and friends while cooking out on the back porch, or at the picnic area by the pool. There is something to offer for everyone. Enjoy the serenity of nature while sitting on the back deck overlooking the pond/canal, or stroll over to the carnival grounds to enjoy the rides, food, and the sights and sounds of years gone by. Sail Away sleeps up to 8 people with 2 queen,1 full, and 1 queen sleeper sofa. We invite you and your family to Sail Away, and enjoy all that the islands have to offer.

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.
Seas The Day is your perfect vacation destination by the Sea! This 3 bedroom, 1 1/2 bath, centrally air conditioned duplex is located in a quiet neighborhood, with large yard, and is the perfect place to enjoy your next family gathering. This home is Located within minutes of a town dock, for the kayak, canoe, and small boating enthusiasts in the family.  Let the wind catch your sails, and take time to “ Seas the Day”.
Serenity On School Street is a charming 1-floor, 2-bedroom, 2-full bath, centrally air conditioned, Island home located close to town.  This home sleeps up to 6 people with 1 King, 1 Queen (futon on wooden frame), and 2 Twin beds (1 regular, 1 trundle).   Location is only a short stroll away from town, where you can enjoy exploring the gift shops, restaurants, bakery, ice cream parlor, library, Robert Reed Downtown Park, and much more.  We invite you to come and find Serenity on School Street.

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 Breeze.  Be one of the first guests to stay in this brand new Island Retreat! Summer Breeze is a 2 bedroom, 2 full bath, centrally air conditioned, cottage, that sleeps up to 6 people with 2 Queen, and 2 twin beds. Enjoy long evenings on the screen porch enjoying the summer breezes, or strolling through town. This home will be available in April. We invite you to let your cares and worries be blown away by the Summer Breeze at this beautiful Island Retreat.

Summer Oasis is an adorable, “Brand new”, 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 Dreams is a 1 bedroom, 1 bath, waterfront condo located on Marsh Island that sleeps up to four people with 1 King or 2 Twin beds (The 2 twin beds can be joined together to make the King Bed), and 1 Queen Sleep Sofa. Enjoy watching sunsets over the water, crabbing, fishing, or just relaxing at this charming Island Retreat. Sunset Views, cool salt breezes and relaxation await you at Sunset Dreams.

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.


Wanna Be By The Sea is a, Charming Island Cottage with 2 bedrooms / 1 bath, window air conditioning, large screen porch, and sleeps up to 7 people, with 2 full, 1 twin (trundle bed) and queen pull out sofa. Nestled among the trees, this home is situated on a spacious yard, perfect for outdoor play. Located less than a mile to Assateague Island and the beach for easy bicycling or walking. Wanna Be By the Sea is also near restaurants, shops, vegetable stands and miniature golf courses. Come and enjoy your Beach Vacation at this Charming Island Cottage!

Warner Landing is a new, beautiful and inviting, 2 bedroom, 1 1/2 bath, centrally air conditioned townhome that sleeps up to 6 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