House - Rating 5 (5)

Smooth Sailing

$135 - $475 / night + taxes & fees

Bedroom 3 bedrooms
Bathroom 2 baths
Guests 8 guests
Pets Not Allowed Pets Not Allowed
Parking Spaces 3 Parking Spaces

  • Address: 5441 Hibiscus Drive
  • Location: Chincoteague, VA
  • Type: House
  • View: Water View
  • Area: 1680 sq. ft.

Location Location

Description Description
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.

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Swipe Swipe for Availability

Bedding Bedding
User User
Bedroom 1
Sleeps: 2
1 Queen

User User User
Bedroom 2
Sleeps: 3
1 Twin
1 Twin Trundle

User User
Bedroom 3
Sleeps: 2
1 King

User User
Living Room
Sleeps: 2
1 Full Sleeper Sofa


Amenities 64 Amenities
Attractions
  • Assateague National Seashore
  • Churches
  • Museums
  • Playground
  • Water Parks
Entertainment
  • DVD Player
  • Television
Essentials
  • Air Conditioning
  • Dryer
  • Extra Pillows & Blankets
  • Hair Dryer
  • Heating
  • Iron & Ironing Board
  • Laptop Friendly
  • Satelite or Cable
  • Washer
Facility
  • Free Parking
  • Laundry
Family
  • Pack & Play Travel Crib
Home Safety
  • Fire Extinguisher
  • Smoke Detector
Indoor
  • Wireless Internet
Kitchen
  • "Keurig" Single Cup Coffee Maker
  • Blender
  • Crock Pot
  • Dishes & Silverware
  • Dishwasher
  • Drip Coffee Maker
  • Full-Sized Refrigerator
  • Kitchen
  • Microwave
  • Oven
  • Pots & Pans
  • Range
  • Spices
  • Steam Pots
  • Toaster/Toaster Oven
Leisure
  • Beach Combing
  • Boating
  • Crabbing
  • Miniature Golf
  • Scenic Drives
  • Shopping
  • Sight Seeing
  • Walking
  • Wildlife Viewing
Location
  • Water View
  • Waterfront
Outdoor
  • BBQ Area
  • Garden or Backyard
  • Kayaking
  • Outdoor Grill
  • Outdoor Shower
  • Screened-In Porch
Special
  • Linens Provided
  • Non-Smoking
Sports
  • Bay Fishing
  • Cycling
  • Golf
  • Pier Fishing
  • Swimming
Themes
  • Away From It All
  • Family
  • Romantic

Reviews Rating 5 (6) Reviews
Rating
Great Getaway!
My family and I had an enjoyable time during our stay at Smooth Sailing -- the great room (kitchen, dining area, and living room) was large and comfortably appointed. The deck afforded lovely views of the canal and even though it was chilly (of course, it's winter!) we enjoyed morning coffee sitting in the screened-in porch. A memorable time was had by all!
Anastasia K - Posted: 2/2/2024
Rating 5
New Years Eve
Had a great time. House was perfect. Had issues w/TV remote and they sent someone right over. Loved the area!
Doug L from Boonton,NJ - Posted: 1/8/2022
Rating 5
The neighborhood is calm and quiet and the house is exceptionally situated to get a real vacation. Excellent. Period.
Rodrigo Alba from Silver Spring - Posted: 9/12/2019
Rating 5
The house was exactly as advertised and the location was wonderful
Mary Pagano from Freeland - Posted: 5/17/2019
Rating 5
We had a lovely, relaxing vacation and really enjoyed renting a house as opposed to staying in a hotel.
Laura Calkins - Posted: 4/30/2019
Rating 5
We loved staying at Smooth Sailing; our stay at Smooth Sailing was all smooth sailing. :-)
Dennis Bours from Washington - Posted: 2/22/2019
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Have a question? Customer Questions & Answers Have a question? Customer Questions & 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?"

Can you swim in the water and use a float in the water? We wanted to know for our stay in July.
Sherri P - Posted: 07/02/2022

Answer:

You are able to swim in the water outside the home, but at your own risk. Please be mindful of currents and aquatic life. 


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