Entire home
Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst
Waterfront holiday home with kitchen and balcony
Photo gallery for Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst





Reviews
9.2 out of 10
Wonderful
3 bedrooms 2 bathrooms Sleeps 8 156.1 sq m
Popular amenities
Explore the area

Chincoteague Island, VA
- Place, Oyster Bay9 min walk
- Place, Maui Jack's Waterpark5 min drive
- Place, Robert N. Reed Downtown Waterfront Park6 min drive
- Airport, Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)84 min drive
Rooms & beds
3 bedrooms (sleeps 8)
1
3 Single Beds
Bedroom 2
1 Queen Bed
Bedroom 3
1 King Bed
Common Space
1 Queen Bed
2 bathrooms
Full Bath 1
Towels provided · Bathtub or shower · Toilet
Full Bath 2
Towels provided · Toilet · Shower only
Spaces
Deck or patio
Kitchen
Garden
Dining area
About this property
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.
"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.
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Amenities
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space
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House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets 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
On-site 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 that there is a smoke detector on the property
About the area
Chincoteague
Located in Chincoteague, this holiday 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. Power boating, fishing and swimming offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.

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
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
About the host
Hosted by Seaside Vacations & Sales

Languages:
English
Premier Host
They consistently provide great experiences for their guests
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