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. 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 2 queen, 1 double, and 1 twin bed. 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 "BRAND NEW" 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.

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.

Home Port is a spacious, 4 bedroom, 2 1/2 bath, central air conditioned, beautiful Island Escape. Make yourself at home while enjoying the cool breezes on large wrap around front porch, or enjoy evening gatherings on the deck or screen porch, located at the back of the home. Homeport is within easy bicycling distance to the Assateague Island National Wildlife Refuge and the nature trails located on Chincoteague Island. Come and enjoy this Beautiful Island Escape.

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.

Kismet is a charming cottage located in a quiet “Beach Community.” This home features a wonderful screen porch with a picnic table and rocking chairs to enjoy leisurely evening gatherings with family and friends. Kismet is close to bike riding trails and the beach on Assateague Island and is within walking distance of restaurants, shops, groceries and much more.

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, pet friendly home, with large fenced yard, 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.

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.

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.

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 calming 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 porches, overlooking the Salt Marshes of Assateague Island, that are abundant with wildlife. Pelican’s Roost has an open floor plan for easy family gatherings and entertaining. Come and enjoy a Calming Island Retreat!

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 ½ 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.

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 Star Cottage is located on quiet East Side Drive, next door to Memorial Park...where you will find a free fishing and crabbing pier, tennis courts, well equipped playground, basketball court, baseball field, pavillion, picnic area, public boat ramp and skateboard park.   Walk to the Park to view the Pony Penning Swim.  House is within walking distance of restaurant, seafood and about 10-15 minute walk  to downtown Chincoteague.

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.

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.

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.

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!
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,
Stephanie Taylor
6759A Maddox Blvd.
Chincoteague Island, VA. 23336
Phone   (757)336-1088
 

Phone (757) 336-1088
Pattjack1@Verizon.net