Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst

Outdoor dining
Fridge, microwave, oven, stovetop
Exterior
Outdoor dining
Exterior
4.6
Outstanding(44 Reviews)

House in Chincoteague Island, VA

8 guests · 4 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Includes essentialsGarden, Pool, Kitchen or Kitchenette and more
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

Smooth Sailing - Work like a Captain, but Play like a Pirate....

"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 & 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 & 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 & 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 & Wall of Windows to the Water are simply stunning. This Home is both open & 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 & 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 & 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.

Amenities

Pool
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Garden

Map of Chincoteague Island, VA

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Reviews

4.6
Outstanding(44 Reviews)
5.0
Jun 2024
Had a wonder stay. Unfortunately it was pretty cold and rainy for a good portion of trip but we did take the canoe out one day. We will definitely be coming back.
5.0
Jun 2024
Great location, lots of amenities.
5.0
Apr 2024
Great location right on the water for kayaking and paddle boarding. Short drive to downtown and the Wildlife Refuge.
5.0
Jan 2024
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!
5.0
Oct 2023
Nice getaway.
5.0
Sep 2023
The property was a wonderful location, quiet and a great view. The house was just right for what we needed, with more than enough space for everyone. Overall, a great place to stay.
5.0
Jul 2023
We loved our stay at Smooth Sailing. Oyster Bay is a beautiful quiet neighborhood and the house is right on the canal with its own dock! There were kayaks and a canoe for us to use. We brought our own bikes, but one bike had a flat tire, and we were so pleased to find there were two cruiser bikes at the house to use! Chincoteague has great bike paths both in town and on Assateague at the beach. We saw all kinds of herons, egrets, ibis and lots of other birds on our rides. The house was clean, nicely decorated and with a screened in porch which was a nice way to enjoy the view without mosquitos! The property managers, Seaside Vacations, were in touch and readily available for anything we might need...and that was nothing, because everything was perfect. We will definitely plan another trip here again!
5.0
Jun 2023
This was our second time renting Smooth Sailing and it was great! This house is in a very nice quiet location with just the right amenities for our family. It appears to have been recently repainted and it feels like the perfect beach house!

FAQs

How much does this house cost compared to others in Chincoteague Island?

The average price for a rental in Chincoteague Island is $341 per night. This rental is $47 above the average.

Is parking included with this house?

Yes, parking is listed as an amenity at Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

Yes, a swimming pool is available for use at Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst. Enjoy the water!

Is Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst?

We found 10 amenities for this rental. This includes pool, air conditioner, kitchen or kitchenette, internet / wifi, and parking.

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