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Best Bayfront Home! No cost Kayak & Bike usage included

Chincoteague, VA, USA
  • House3000 sqft
  • Bedrooms3
  • Sleeps8
  • Bathrooms3
  • Half Baths0
  • Mininum Stay7 nights

House, 3 Bedrooms + Convertible bed(s), 3 Baths, (Sleeps 6)

You will never want to leave this home magnificently set in a private bayfront area overlooking oyster and clam beds, a marshy bird filled 'tump', and enjoying a panoramic view of Oyster Bay and Assateague Island. Kayak, swim, bird watch, bike, sun bathe, fish and crab, or just relax, lounge, read or enjoy a cocktail on the screened in porch or any deck. An exciting architectural design, local artwork including carvings, paintings and artifacts, an eclectic book collection, and hi tech amenities such as Wi-Fi, LCD TVs with Netflix, Stereo, iPod docking station will compete for your attention.

The kitchen will delight any chef, the wet bar makes entertaining easy, a bumper pool table adds to the fun, a separate TV room, keeps the noise away. Two fireplaces add to the ambiance. Upstairs bedrooms are configured to create a master suite, bath and tower lookout on one side of the house, and on the other side is a bedroom with private balcony, and a separate twin bedded room and a main bathroom with a jacuzzi tub.

Relax at Sunrise View

We truly have the million dollar view! The house is a marvelous place to 'hang out'. The scenes are ever changing. The water birds are always a delight to watch. Star gazing is great. Hear the ocean waves from Assateague, or see wild ponies grazing across the bay. Take a cup of coffee or a cocktail up to the tower and enjoy the views. The property has 200 ft. of waterfront on Oyster Bay - to the left there is a park- like feel.

In front along the water's edge, there is plenty of room to throw in a fishing line (seasonal flounder and stripped bass are caught), or a crab line or a crab pot. Listen to the call of the gulls, and watch the Osprey soar. Take a kayak (2 included with the rental) on a little water/ marsh adventure. Boat to Assateague, clam or explore - minimal boat traffic. Sunbathe, relax on the decks with your favorite book, smell the salt air, feel the breeze, unwind, relax. It's paradise!!!

Enjoy the Beach and the Food

The beach on Assateague is fantastic (8 min. ride by car). Voted one of the 10 best beaches in America, it is natural and wild in places, yet offers beaches with life guards in the main approach area. Tom's Cove on the bayside of the beach is no more than 200 yards away - for a no wave swim. The sand is pristine. Surf fish if you like. Watch the dolphins. Picnic at the beach, use our chairs and cooler. - (also 'necessary rooms' on site). For a fun change take a bike (5 included in the rental) to the beach and enjoy a ride along the Assateague wild life trail on the way home.

On the way home stop for fresh seafood at Howard's - just around the corner from the house, and pick up fresh oysters, clams, mussels, crabs, lobsters, scallops, or fish - you'll have a great dinner on the porch. If you don't want to cook, AJ's on the Creek, Bill's and others, will provide you with some very good fare (we will provide you a restaurant guide). For a culinary delight, a charming town, a nice walk along the Creek, drive to Onancock for the evening - 5+ wonderful restaurants - 50 minutes south.

Activities and Exploring

Chincoteague was voted the best Beach Town in America - see why...Be on the lookout for the Chincoteague Ponies in the wild. Visit the Batemen Wildlife Center on Assateague and sign up for the Wildlife Tram Tour - learn about the island ecology, ponies and water fowl. Visit the Oyster Museum (Chincoteague history), bike around the islands - both Chincoteague and Assateague, rent a motorboat and fish, take a sightseeing tour by water, a sunset cruise, play miniature golf, see a first run movie, buy homemade ice cream at the Island Creamery (voted the #1 ice cream in America), shop til you drop at the many unique boutiques, gift shops, bookstores and galleries. Go to the Fireman's Carnival (July 1- Aug. 7 weekends).

The Pony round-up, swim, and auction week is extra special (July 26th week). Watch the 'Misty of Chincoteague Video. Visit the NASA museum just off the island. Head north or south for adventure - discover Eastern Shore delights ... or simply savor the delights of Chincoteague and immerse yourself in Island life.

Keywords: Bayfront home, waterfront, water view, kayaking


Chuck Maddox

Member Since 2010
Response rate:
Response time:
within a few hours
english, german, polish, polish
Calendar last updated:
Apr 17, 2018
About Chuck Maddox

Both of us fell in love with Chincoteague Island a long time ago... when we were in our late 20's. We fell in love with it's unspoiled beaches, the wildlife, the ponies and the pleasant,low key feel of the island and its people. Our children and our grandchildren have grown up loving the island and our house. We have had reunions, wedding receptions and just plain fun there. We are now retired, and just started renting our house, but only for a limited number of weeks. It is a home for us, but we decided we would share it with selected renters, whom we feel confident will enjoy it and take care of it just like we do.

Chuck Maddox purchased this House in 1986

Why Chuck Maddox chose Deep Hole

This is our second home on Chincoteague, and while we loved our first house, a canal front property, we knew we wanted to be directly on the bay - and specifically Oyster Bay. The views on the bay are second to none. So when we looked for a new place, it had to be there. When my wife saw the house we now own, she said very demonstrably - 'I want this house' even though the original was nothing like it is today. With a bird filled marsh and oyster beds right in front, and perfect views of Morris and Assateague Islands, we have incomparable views. Our friends all say we truly have the 'million dollar view'. Add great wildlife viewing and excellent water to boat and kayak on, we really have the perfect spot.

What makes this House unique

We redesigned the house to look great but most important to be comfortable, functional, and be a place where you really get away from it all. Peace and serenity abide here. We maximized our water views. The light flows everywhere so there is always a cheery feel to the place. We like to entertain - and the open flow of rooms, fireplaces, wet bar, bumper pool, and sound system facilitate that. The decks, along with comfortable outdoor furniture, allow you to read and sun bathe, and soak in the views. The screened porch offers waterfront dining. The tower gives you a great long distance observation place to sit and sip a coffee or a have a drink. Boating, kayaking, swimming, and fishing are right in the backyard. It's a truly wonderful place to be!


    • Internet
    • Air Conditioning
    • Heater
    • Fireplace
    • Satellite or Cable
    • Washer & Dryer
    • Parking
    • TV
    • No Smoking


      • 3 Bedrooms, Sleeps 8
      • Bedroom 1
        1 queen
      • Bedroom 2
        1 queen
      • Bedroom 3
        2 twin/ single
      • Convertible bed(s)
        1 queen
      • Queen size Beds (2) With Pillow top mattresses for ultra comfortable sleeping, Twin or Single Beds (2), Sleep Sofa or Futons (1) queen size. All with water views.


      • 3 Bathrooms
      • Bathroom 1
        toilet, shower
      • Bathroom 2
        toilet, combination tub/shower, jetted tub
      • Bathroom 3
        toilet, shower
      • hair dryers in all bathrooms

      Location Type

        • Beach
        • Waterfront
        • Waterfront
          200' on Oyster Bay. Magnificent views of Morris Is. & Assateague Is. The best sunrises. Birding, fishing, crabbing, swimming. Boating & kayaking right from the house. A truly serene, peaceful location


            • Away From It All
            • Family
            • Romantic
            • Sports & Activities


                • Guests provide their own meals


                    • Local Activities Guide
                    • Activities Guide
                    • Alarm Clock
                    • Backpack
                    • Basic Soaps
                    • Ceiling Fans
                    • Clothes Dryer
                    • Filtered Water
                    • Fireplace
                    • Firewood
                    • Gas Fireplace
                    • Hair Dryer
                    • Heating
                    • Internet
                    • Iron & Board
                    • Laundry Soap
                    • Linens Provided
                    • Living Room
                    • Air Conditioning
                    • Local Maps
                    • Local Restaurant Guide
                    • Paper Towels
                    • Parking
                    • Parking Off Street
                    • Parking for RV/Boat/Trailer
                      Enough space in the drive way for a trailered boat and several cars. RV's not permitted.
                    • Shampoo
                    • Sofa Bed
                    • Telephone
                      for local calls only
                    • Telescope
                    • Thermos Bottle
                    • Toilet Paper
                    • Towels Provided
                      beach towels provided, others are OPTIONAL
                    • Washing Machine
                    • Water Cooler
                    • Wireless Internet
                    • Wood Fireplace
                    • Wood Stove


                        • Kitchen
                          Glasstop stove with warming drawer, chopping block, coffee maker & bean grinder, instant hot water, and more...
                        • Blender
                        • Coffee Maker
                        • Cooking Utensils
                          Most everything you'd want.
                        • Dishes & Utensils
                          Top quality
                        • Dishwasher
                          nice and quiet
                        • Freezer
                        • Ice Maker
                        • Coffee Grinder
                        • Lobster Pot
                        • Microwave
                        • Oven
                        • Pantry Items
                          lots of spices
                        • Refrigerator
                          with ice maker and filtered water
                        • Stove
                        • Stove
                        • Toaster
                          4 slice.


                            • Dining
                              on the porch, or inside table with extra leaves more can be seated
                            • Dining Area
                            • comfy seating for 8 people


                                • Music Library
                                  Also a iPod docking station
                                • Books
                                • Books for Kids
                                • CD Player
                                • DVD Player
                                • Game Room
                                • Games
                                • Games for Kids
                                • Books for Adults
                                • Pool Table
                                  bumper pool
                                • Radio
                                • Satellite / Cable
                                  HD service. 1- 40' TV & 2 other HD TV's, Netflix
                                • Stereo
                                • Television
                                • Toys
                                • VCR
                                • Video Library


                                    • Kayak / Canoe
                                      Kayaks: 1 double and 2 singles included with rental
                                    • Balcony
                                      off MBR
                                    • Beach Towels
                                    • Bicycles
                                      4 adult size, 1 child
                                    • Binoculars
                                    • Boat Dock
                                    • Boat with Paddles
                                    • Crow's Nest
                                    • Deck / Patio
                                      Spacious rear and side decks. Waterside screened -in porch with stereo speakers. Plenty of comfortable seating and lounging.
                                    • Beach Chairs
                                    • Large Cooler
                                    • Lawn / Garden
                                    • Outdoor Grill
                                      gas and charcoal grills
                                    • Outdoor Grill Gas
                                    • Porch / Veranda
                                      Screened. For great waterside dining and views. Glass top circular table and comfortable chairs.
                                    • Screen Porch / Veranda
                                    • Small Cooler
                                    • Unscreened Porch / Veranda
                                    • Wood Deck


                                        • unsuitable for elderly or infirm
                                        • wheelchair inaccessible

                                          Pool / Spa

                                            • jetted tub


                                                • museums
                                                • autumn foliage
                                                • churches
                                                • cinemas
                                                • coin laundry
                                                • festivals
                                                • health/beauty spa
                                                • library
                                                • marina
                                                • bay/sound
                                                • playground
                                                • pond
                                                • recreation center
                                                • restaurants
                                                • theme parks
                                                • water parks
                                                • winery tours
                                                • zoo

                                                  Leisure Activities

                                                    • photography
                                                    • antiquing
                                                    • bird watching
                                                    • boating
                                                    • eco tourism
                                                    • horseback riding
                                                    • miniature golf
                                                    • beachcombing
                                                    • scenic drives
                                                    • shelling
                                                    • shopping
                                                    • shuffleboard
                                                    • sight seeing
                                                    • walking
                                                    • wildlife viewing

                                                      Local Services & Businesses

                                                        • ATM/bank
                                                        • Babysitter
                                                        • fitness center
                                                        • groceries
                                                        • hospital
                                                        • laundromat
                                                        • massage therapist
                                                        • medical services

                                                          Sports & Adventure Activities

                                                            • pier fishing
                                                            • basketball court
                                                            • deepsea fishing
                                                            • fishing
                                                            • fly fishing
                                                            • freshwater fishing
                                                            • golf
                                                            • hiking
                                                            • hunting
                                                            • hunting small game
                                                            • jet skiing
                                                            • kayaking
                                                            • parasailing
                                                            • cycling
                                                            • roller blading
                                                            • sailing
                                                            • scuba diving or snorkeling
                                                            • snorkeling
                                                            • snorkeling/diving
                                                            • sound/bay fishing
                                                            • surf fishing
                                                            • surfing
                                                            • swimming
                                                            • tennis
                                                            • water skiing
                                                            • water tubing
                                                            • wind-surfing


                                                                • Bumper pool table, iPod docking station, 5 bikes, 2 kayaks Boat tie-up at the house, boat ramp within the community

                                                                  17 Reviews


                                                                  Latest reviews

                                                                  The ponies aren't the only ones to love Chincoteague

                                                                  Robin M.Chester County, PA

                                                                  The house on Oyster Bay was beautifully decorated and very comfortable for our Family of 4 plus 2 friends. Lots of room for everyone and plenty of places to curl up with a good book. Favorite things to do were swimming in the Bay at slack time (the current move briskly during the changing of tides), kayaking the bay, riding bikes to see the pony swim, and spending every moment we could on the beautiful beaches of Asateague at the National Park! We ate most of our dinners in making locally caught seafood nearly every night on the screened in porch overlooking Oyster Bay. We splurged on Donuts from the truck by "thirsty Mosquito" (sorry I don't remember the name but so worth standing in line for) and ice cream from The Creamery! I suggest getting a single cone because two scoops has got to be a pint of ice cream or more! One of the best beach vacations we have ever had! Thank you for sharing your beautiful home!

                                                                  Oyster Bay Gem!

                                                                  James O.

                                                                  We spent five weeks enjoying life on Oyster Bay. This beautiful home lives comfortably for a smaller group. There were six of us at times and other times it was just my wife and I. The house was always perfect for our needs.The kitchen was super well equipped. We ate almost all our meals in because we couldn't imagine not spending every moment we could on the screen porch overlooking the water. After five weeks we were in sync with the birds and the oystermen. And we were not ready to go home!

                                                                  Bayfront Beauty

                                                                  Tracy C.

                                                                  Beautiful property, pictures don't do it justice! The house is in a quiet neighborhood close to everything there is to see and do. It is beautiful inside and out and outfitted with everything needed to have a wonderful vacation.

                                                                  Loved it

                                                                  MariseEustis fl

                                                                  We rented the home for a week and it was most enjoyable. The view from the porch was just breathtaking. Everything we needed was provided. The kitchen was very well equipped even had a hand mixer to I could make a birthday cake for my daughter in law . Lots of space for everyone to spread around.


                                                                  Cyndy B.Chincoteague Island, VA

                                                                  Amazing home - very comfy beds - beautiful amenities!

                                                                  Owner's Response:

                                                                  Thanks!! Glad you had a great stay.

                                                                  Excellent Home

                                                                  Maralyn W.Roe Green , Manchester

                                                                  Very enjoyable 6 days in Chintogeauge! The house was beautiful, clean, comfortable and contained everything you could need or want. We were very impressed. As this was our first trip from the UK to the area and the first time we have booked through VRBO. we were very happy with the booking arrangements and the description of the house on VRBO - all went very smoothly. Thank you!


                                                                  Chincoteague, VA, USA

                                                                  Chincoteague Island is rated the #1 Beach town in America... Lots of outdoor activities, and for museum lovers the NASA Museum, and Chincoteague Museum are only a few minutes from the house. Occasionally the NASA Wallops base... launches satellites too!

                                                                  Rates & Availability

                                                                  Additional information about rental rates

                                                                  Damage Insurance
                                                                  Tax Rate

                                                                  Pony Penning Week rents for $3345 plus taxes for the week. There is no extra cleaning fee, and the use of the provided bikes and kayaks are included in the rental price. Optional sheet and towel service is available. Cancellations: A cancellation of a confirmed reservation 90 days or more prior to the rental date shall have the option of changing, within the same calendar year, to an available rental date with the same rental rate. A cancellation with less than 90 days prior to the rental date will receive a refund only if the property is re- rented for the same rate and time. Renter must agree to the rental agreement located under Attachments on this site. Also please note children under 8 years old are not allowed; and while no security deposit is collected, the renter must purchase a Damage Protection Policy ($79) - details will be provided.

                                                                  17 Reviews
                                                                  Wonderful 4.8/5
                                                                  Enter dates for accurate pricing
                                                                  For booking assistance, call 888-640-7927

                                                                  Property # 288026vb