Title: Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst - Latest Reviews, Deals & Photos 2025 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst ![Dining](https://images.trvl-media.com/lodging/33000000/32710000/32702800/32702731/2cac0240.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Interior](https://images.trvl-media.com/lodging/33000000/32710000/32702800/32702731/9bd8da1a.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32710000/32702800/32702731/dd84901d.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior](https://images.trvl-media.com/lodging/33000000/32710000/32702800/32702731/bda10b2e.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32710000/32702800/32702731/42289cdc.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Amenities - Policies - Location Smooth Sailing on Chincoteague Island is a serene retreat nestled in exclusive Oyster Bay, surrounded by Whispering Pines and overlooking the Canal. Unwind in the beautifully decorated Screened Porch or enjoy water views from huge windows while lounging on an oversized Sectional Sofa in the Living Room. 9.2 Wonderful ### Entire home 3 bedrooms2 bathroomsSleeps 81680 sq ft ## Popular amenities - Dryer - Parking available - Washer - Kitchen - Barbecue grill - Air conditioning ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire home to yourself and will only share it with other guests in your party. ### Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst 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. ## Property amenities ### Internet - Available in the house: Free WiFi ### Parking and transportation - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Microwave - Oven - Refrigerator - Spices - Stovetop - Toaster ### Dining - Dining table ### Bedrooms - 3 bedrooms - Bedsheets provided ### Bathroom - 2 bathrooms - Bathtub or shower - Shower - Towels provided ### Living spaces - Dining table - Living room ### Entertainment - Flat-screen TV with cable channels ### Outdoor areas - Barbecue grill - Dock - Garden - Outdoor furniture - Patio ### Laundry - Laundry facilities - Washing machine ### Comfort - Air conditioning - Heating ### Pets - No pets allowed ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Iron/ironing board ### Location highlights - On the waterfront ### Things to do - Water park - Cycling nearby - Fishing nearby - Golfing nearby - Motor boating nearby - Swimming nearby - Wildlife walks nearby ### Safety features - Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector) - Smoke detector (host has indicated there is a smoke detector on the property) ### General - Garden - Unit size: 1,680 square feet ## Policies ### Check-in Check-in time starts at 4:00 PM Minimum check-in age: 25 ### Check-out Check-out before 10:00 AM ### Special check-in instructions You will receive an email from the host with check-in and check-out instructions ### Pets Pets not allowed ### Children and extra beds Children are welcome ### Events No events allowed ### Smoking Smoking is not permitted ## Important information ### You need to know Extra-person charges may apply and vary depending on property policy Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed Onsite parties or group events are strictly prohibited Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip Host has indicated there is a smoke detector on the property This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation ### Property is also known as 150425 ## About the area Located in Chincoteague, this vacation home is on the waterfront. Captain Timothy Hill House and Assateague Lighthouse are local landmarks, and the area's natural beauty can be seen at Chincoteague National Wildlife Refuge and Oyster Bay. Maui Jack's Waterpark and Wallops Flight Facility are also worth visiting. Motor boating, fishing, and swimming offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby. [Visit our Chincoteague travel guide](https://www.expedia.ca/Chincoteague.dx55637) [View more Vacation homes in Chincoteague](https://www.expedia.ca/Chincoteague-Private-Vacation-Homes.d55637-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C37.94369%2C-75.35039&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=jFkcMZTaZvk5Li9R4CYVlLo7M6M=) Chincoteague Island, VA ### What's nearby - Oyster Bay - 9 min walk - 0.8 km - Captain Timothy Hill House - 5 min drive - 2.8 km - Maui Jack's Waterpark - 5 min drive - 3.1 km - Robert N. Reed Downtown Waterfront Park - 6 min drive - 3.9 km - Museum of Chincoteague - 7 min drive - 3.8 km ### Getting around - Ocean City, MD (OCE-Ocean City Municipal) - 76 min drive ### Restaurants - ‪McDonald's - ‬6 min drive - ‪Island Creamery - ‬4 min drive - ‪Ropewalk - ‬5 min drive - ‪Teaguers - ‬3 min drive - ‪Steamers - ‬4 min drive ## Frequently asked questions ### Is Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst pet-friendly? > No, pets are not allowed at this property. ### What time is check-in at Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst? > Check-in begins at 4:00 PM. ### What time is check-out at Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst? > Check-out is at 10:00 AM. ### Where is Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst located? > Situated on the waterfront, this vacation home is 0.4 mi (0.7 km) from Oyster Bay and within 3 mi (5 km) of Maui Jack's Waterpark and Captain Timothy Hill House. Chincoteague Channel and Robert N. Reed Downtown Waterfront Park are also within 3 mi (5 km). ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. 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