Smooth Sailing

$135.00 - $561.00 /Night
Average Rating

Address: 5441 Hibiscus Drive Location: Chincoteague Island Type: House Area: 1680 sq. ft.
3 Bedrooms 2 Baths Sleeps 8 Pets Not Allowed Parking Spaces: 3 Linens Provided
Bedroom 1
1 Queen
Bedroom 2
1 Twin, 1 Twin Trundle
Bedroom 3
1 King
Living Room
1 Full Sleeper Sofa
Fabulous Updates for 2022!!

"We cannot control the wind, but we can direct the sail" - Life is busy. It gets more and more difficult to find that cherished time with family and friends. This is the sole purpose of Smooth Sailing on Chincoteague Island. It is a retreat. A destination. A place to rejuvenate and reconnect with those who matter the most. This wonderful Home was created for just that.

Located in exclusive Oyster Bay, Smooth Sailing is in the heart of the island, yet feels a million miles away. Surrounded by Whispering Pines and located directly on the Canal, its serenity will embrace you even as you pull into the driveway. This fabulous Home makes the most of both Outdoors Living and Indoor Comfort. With 3 Bedrooms and 2 Full Baths, it sleeps 8 more than comfortably. Before you even enter the house, you'll want to run to the backyard and take in those Views and that Salty, Sweet Bay Breeze. 

Upon entering Smooth Sailing through the fabulous and beautifully decorated Screened Porch, you're already thinking what a great place this would be to sneak away with a good book. Opening the door, the Soaring Ceiling and Wall of Windows to the Water are simply stunning. This Home is both open and cozy at the same time. The Living Room features an oversized Sectional Sofa you'll love sinking into after a fun-filled day on the Beach, Flat Screen Cable TV, and of course, Free WiFi. Light, bright, and beachy  with colors of Sand and Sea throughout, you can relax and still take in the Water Views from the huge windows. 

The Open Floor Plan at Smooth Sailing is perfect for gathering and entertaining. The Living Area opens to the spacious Dining Area and Kitchen, with plenty of room for all at the Dining Table and Breakfast Bar. Even the Chef in the family can take in fabulous views while preparing the Fresh Catch of the Day. Dine indoors in the Central AC or Al-Fresco on the Waterfront Deck, while listening to the Tree Frogs. 

Also on the 1st Floor are 2 Bedrooms and a Full Bath with Tub/Shower Combo. Bedroom 1 has 2 comfy Twin Beds and a Twin Trundle. Adorned in Nautical Navy with a fun Whale Theme, it 's just a great place to spend time. Right next door is Bedroom 2, with a Queen Bed, decorated with a Nautical Flair. You'll love the Custom Tilework in the Full Bath, which is convenient to both the Living Area and Bedrooms. Follow the Warm Wood Railing upstairs, and you'll fine a Loft overlooking the Living Area, as well as the Master Bedroom with luxurious King Bed and Flat Screen TV. The Master Bath has a Walk-in Shower and lovely vanity.

If the Indoor Living at Smooth Sailing isn't enough, just wait until you check out the backyard, aka Paradise. Being directly on the Canal certainly has its advantages. The kids (and the kid in you) will delight in fishing and crabbing right from your Private Dock. Bring your Kayaks and launch them in the calm canal water. Don't have kayaks? Let us know and we can help you arrange to have them delivered when you arrive. With a depth of roughly 2 1/2 feet, feel free to bring your boat! Direct access to the Bay is right at the end of the canal - the flounder are waiting for you! And there's nothing better than relaxing in the Swing under the house with a glass of wine as the sun sets. Just pure paradise.....what are YOU waiting for?

Smooth Sailing - Catch the Wind in your Sails. Explore. Dream. Discover. 
Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored.

SwipeDrag for Availability



  • Assateague National Seashore
  • Churches
  • Museums
  • Playground
  • Water Parks


  • DVD Player
  • Television
  • Satellite or Cable


  • Laptop Friendly
  • Washer
  • Iron & Ironing Board
  • Heating
  • Extra Pillows & Blankets
  • Cable
  • Air Conditioning
  • Dryer


  • Laundry (Washer / Dryer)
  • Free Parking


  • Pack & Play Travel Crib

General Indoor Amenities

  • Wireless Internet

Home Safety

  • Fire Extinguisher
  • Smoke Detector


  • Drip Coffee Maker
  • Range
  • Oven
  • Full-Sized Refrigerator
  • "Keurig" Single Cup Coffee Maker
  • Crock Pot
  • Toaster/Toaster Oven
  • Dishwasher
  • Pots & Pans
  • Kitchen
  • Steam Pots
  • Spices
  • Microwave
  • Dishes & Silverware
  • Blender


  • Crabbing
  • Walking
  • Wildlife Viewing
  • Sight Seeing
  • Shopping
  • Scenic Drives
  • Miniature Golf
  • Boating
  • Beach Combing


  • Water View

Location Type

  • Waterfront


  • Kayaking
  • BBQ Area
  • Garden or Backyard

Outdoor Amenities

  • Outdoor Shower
  • Screened-In Porch

Outdoor Grill

  • Gas Grill


  • Linens Provided
  • No Smoking


  • Cycling
  • Fishing - Bay
  • Swimming
  • Pier Fishing
  • Golf


  • Romantic
  • Family
  • Away From It All
(5) Reviews
SwipeDrag for Reviews
Questions and Answers
Want to know specifics? Ask anything about this specific property that you would like to know...
Example: “Is the balcony screened in?” or “Is there a toaster oven?”
Request More Info
Want to know specifics? Ask anything in reference to vacationing at this property that you would like to know...
Example: “Are fresh linens Provided?”
Leave this field empty
This Property has been looked at 17 times in 24 hours

Find Available Dates For this Property