Title: Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&selected=32702731&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 Waterfront vacation home with kitchen and balcony ## Photo gallery for Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst ![Interior - Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst (Chincoteague Island)](https://images.trvl-media.com/lodging/33000000/32710000/32702800/32702731/8589feac.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Fridge, microwave, oven, stovetop - Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst (Chincoteague Island)](https://images.trvl-media.com/lodging/33000000/32710000/32702800/32702731/dd84901d.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior - Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst (Chincoteague Island)](https://images.trvl-media.com/lodging/33000000/32710000/32702800/32702731/43cdd5b1.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior - Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst (Chincoteague Island)](https://images.trvl-media.com/lodging/33000000/32710000/32702800/32702731/9bd8da1a.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Flat-screen TV - Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst (Chincoteague Island)](https://images.trvl-media.com/lodging/33000000/32710000/32702800/32702731/3a8805b2.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies 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. ## Reviews 9.2 Wonderful ### Entire home 3 bedrooms2 bathroomsSleeps 81680 sq ft ## Popular amenities - Kitchen - Washer - Dryer - Free WiFi - Air conditioning - Outdoor Space ## 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 ## Similar properties ![Exterior](https://images.trvl-media.com/lodging/33000000/32710000/32702900/32702830/623160eb.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Ariel\`s Grotto is a gorgeous 3 Bedroom/2.5 Bath Vacation Rentals on incredible C Chincoteague Island - Kitchen - Washer - Dryer - Free WiFi 9.6 Exceptional 90 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-06&endDate=2026-02-07&selected=32702830&PinnedHotelID=32702830&HadPinnedHotel=true®ionId=-1&adults=2) ![TV](https://images.trvl-media.com/lodging/115000000/114210000/114205900/114205900/0b5c8a73.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Oyster Bay Oasis - 5 Min to Assateague! 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Chincoteague Island - Kitchen - Washer - Dryer - Air conditioning 8.0 Very good 1 review [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-06&endDate=2026-02-07&selected=92196955&PinnedHotelID=92196955&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach](https://images.trvl-media.com/lodging/97000000/96530000/96522000/96522000/fc8999f0.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Your next Vacation is Shore to Please! Chincoteague Island - Kitchen - Washer - Dryer - Pet friendly 10 Exceptional 5 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-06&endDate=2026-02-07&selected=96522000&PinnedHotelID=96522000&HadPinnedHotel=true®ionId=-1&adults=2) ![TV](https://images.trvl-media.com/lodging/91000000/90540000/90535100/90535017/c9cc68ed.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Blue Sea Star - Beautiful Pet Friendly Home! Chincoteague Island - Kitchen - Washer - Dryer - Pet friendly 10 Exceptional 1 review [](https://www.expedia.ca/Hotel-Search?startDate=2026-02-06&endDate=2026-02-07&selected=90535017&PinnedHotelID=90535017&HadPinnedHotel=true®ionId=-1&adults=2) ## 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 Information provided by the property may be translated using automated translation tools ### 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 has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room 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 on the waterfront, this vacation home is in Deep Hole, a neighborhood in Chincoteague. 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 - ![This is an aerial of an abandoned oyster house along the shores of Chincoteague Bay on George Island Landing, a declined oyster, clam, and crab fishing village in Maryland.](https://images.trvl-media.com/place/553248635976194259/d37dc043-6237-4036-9c01-c39a8be2fa02.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Oyster Bay 9 min walk \- 0.8 km - ![You can go up to the top of this beautiful lighthouse.](https://images.trvl-media.com/place/6075486/8445f124-632b-4b47-8518-f3362d880da3.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Chincoteague National Wildlife Refuge 6 min drive \- 4.5 km - Maui Jack's Waterpark 4 min drive \- 3.1 km - Robert N. Reed Downtown Waterfront Park 5 min drive \- 3.9 km - University of Maryland Eastern Shore 49 min drive \- 72.6 km ### Getting around - Ocean City, MD (OCE-Ocean City Municipal) 76 min drive ### Restaurants - Island Creamery 4 min drive - McDonald's 6 min drive - Teaguers 3 min drive - Steamers 4 min drive - Famous Pizza & Sub Shoppe 5 min drive ## Frequently asked questions ### Is Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst pet-friendly? ### How much is parking? ### What time is check-in at Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst? ### What time is check-out at Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst? ### Where is Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst Reviews ## Reviews ### Wonderful All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative. [More information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 36 8 - Good 6 6 - Okay 3 4 - Poor 1 2 - Terrible 1 ### 8.8 Cleanliness ### 9.8 Location ## Reviews ### 10/10 Excellent #### Jeff S. Oct 5, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy House is very well equipped for cooking and entertainment ##### Jeff S. Stayed 3 nights in Sep 2025 ### 10/10 Excellent #### Heidi C. Sep 28, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great vacation It was a great location with all the amenities ##### Heidi C. Stayed 7 nights in Sep 2024 ### 10/10 Excellent #### Jeffrey M. May 19, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### No regrets Listing was accurate. Location was excellent. Property managers were responsive when contacted. I would stay here again. ##### Jeffrey M. Stayed 7 nights in May 2025 ### 10/10 Excellent #### Sean B. Apr 4, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### First time visiting Chincoteague Great location right on the water for kayaking and paddle boarding. Short drive to downtown and the Wildlife Refuge. ##### Sean B. Stayed 4 nights in Mar 2024 ### 10/10 Excellent #### Verified traveller Jun 22, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Beautiful home and location. 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. ##### Verified traveller Stayed 4 nights in Mar 2024 ### 10/10 Excellent #### Lisa G. Sep 25, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Wonderful 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. ##### Lisa G. Stayed 7 nights in Sep 2023 ### 10/10 Excellent #### Anastasia K. Jan 5, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### 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. Stayed 7 nights in Dec 2023 ### 8/10 Good #### Tessa E. Apr 2, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Quiet, Adult Friendly Retreat Overall the house is nice. We love curling up on the couch and watching movies or sitting out on the benches watching the wildlife. The main issue is the loft. I’m guessing it was renovated without a permit because there is no world in which it would pass inspection. The stairs are abnormally narrow and pose a fall risk. The railing has huge gaps that an adult could easily fit through, much less a child. If you’re staying here with young kids, be prepared to watch them like a hawk. Additionally , there’s something weird with the HVAC up there. We ended up having to move downstairs into the twin bedroom because the master was so unbelievably hot. There’s a single, huge vent in the master bath that pours hot air into the second floor. It was easily 85 degrees up there each morning unless we turned off all the heat and opened the windows. The neighborhood is nice, very quiet and friendly. Great for walks. Not the house’s fault, but some of y’all need to learn how to clean a dish. The kitchen is very well stocked, but you’ll need to wash anything before you use it. People apparently don’t do their dishes on vacation now. ##### Tessa E. Stayed 6 nights in Mar 2025 ### 10/10 Excellent #### Howard W. Jun 22, 2020 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great weekend getaway Clean and good location and we met some friendly neighbors! ##### Howard W. Stayed 3 nights in May 2020 ### 10/10 Excellent #### Thomas C., Alexandria, VA Sep 11, 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Chincoteague vacation Nice, quiet setting with all the amenities we needed. ##### Thomas C. Stayed 7 nights in Aug 2021 ### 10/10 Excellent #### Ralph A. Jun 15, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Chinco Vacay Great location, lots of amenities. ##### Ralph A. Stayed 7 nights in Jun 2024 ### 10/10 Excellent #### Alex C. Jan 31, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Excellent property! Everything as described! Will come again!!! ##### Alex C. Stayed 4 nights in May 2022 ### 10/10 Excellent #### Erin B., Kutztown, PA, USA Jun 12, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great for family Spent a week here with my extended family - we loved it! It was a great place to lounge with the baby, take our boat out and cook some local seafood. The neighborhood is quiet and we enjoyed some peaceful, beautiful sunrises on the back deck watching the birds. The outdoor shower was a great feature after a beach day. We'd definitely stay here again. ##### Erin B. Stayed 6 nights in Jun 2023 ### 10/10 Excellent #### Robert V., Boulder, CO USA Oct 29, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great Nice getaway. ##### Robert V. Stayed 3 nights in Oct 2023 ### 10/10 Excellent #### Alexandra H. Mar 29, 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Short family get-away The property was perfect for us — very cozy and compact, three bedrooms which slept all seven of us, very lovely situated on the canal with pretty view, had a deck AND a screened-in porch, plus a great family room. It had everything we wanted for a comfortable and relaxing break. Wish we could have stayed longer. ##### Alexandra H. Stayed 5 nights in Mar 2021 ### 8/10 Good #### Jemma L. Dec 29, 2020 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Christmas getaway The lodge is located right on the water and is a really fabulous place to stay. We booked a last minute trip over Christmas and it was perfect for us. We have a 4 year old and a 9 month old and the house was great. We cooked a full Christmas dinner whilst staying there and the kitchen could not be better appointed. ##### Jemma L. Stayed 3 nights in Dec 2020 ### 10/10 Excellent #### Cheri H., Mercer, PA Jun 27, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Smooth Sailing! 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! ##### Cheri H. Stayed 7 nights in Jun 2023 ### 8/10 Good #### Julie M., Washington, DC Mar 26, 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Tranquil on the Water The property is very nice. The windows are beautiful and there is a nice deck and screened porch. It’s very close to town - bring a bike and you’ll be there in a jiff. ##### Julie M. Stayed 3 nights in Mar 2021 ### 10/10 Excellent #### Steve D. Aug 29, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### First time VRBO user very satisfied. Everything in the house worked. Communication was good and there were issues during our stay ##### Steve D. Stayed 7 nights in Aug 2022 ### 10/10 Excellent #### Pamela F. Jul 23, 2020 Liked: Check-in, communication, location, listing accuracy #### Lovely week We had a lovely week, Chincoteague has so much to offer and we had a wonderful week. The house had a great set up for our family of 5 and we loved the toys and games. Not sure the cleaning crew had finished their work before we got there, but I would still highly recommend a trip to Chincoteague! ##### Pamela F. Stayed 7 nights in Jul 2020 ### 10/10 Excellent #### charles b. Apr 23, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Smooth sailing Was definitely one of best experiences ever thank you for the wonderful customer service and will definitely be doing business again soon ##### charles b. Stayed 6 nights in Apr 2023 ### 10/10 Excellent #### Jessica M. Nov 27, 2022 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Perfect waterfront kids friendly property We spent Thanksgiving in Chincoteague to celebrate with family members who live on the island . The house was absolutely perfect for us. It was clean and had everything we needed. Our toddler enjoyed the kids room which featured many toys and arts/ crafts supplies. The water views were stunning . We will be back ! ##### Jessica M. Stayed 3 nights in Nov 2022 ### 10/10 Excellent #### William A. Jun 22, 2020 Liked: Cleanliness, communication, location, listing accuracy Disliked: Check-in #### Great spot in a nice neighborhood on Chincoteague Island Great place on a great island. Check in process was a little frustrating because I never received the welcome email with the relevant info, but a call to the after-hours line and a short 5-10 minute wait on the patio, and we were in with no additional problems. Would recommend to anyone looking to get away to this great ocean/bay side community. Also, Gary Howard's Seafood is really close to the rental and has the best fresh seafood in town! Highly recommend! ##### William A. Stayed 3 nights in Jun 2020 ### 10/10 Excellent #### Diane J. May 11, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Weekend Surf Fishing Trip We enjoyed a wonderful stay at Smooth Sailing Cottage with our friends! We spent most of our cottage time on the screened-in porch. The kitchen was well-stocked. The beds were comfy. The cottage was clean. The communication with the Seaside staff was great. If we had stayed one more day, we would have liked to kayak the canal. Wonderful place to relax at Chincoteague! ##### Diane J. Stayed 3 nights in May 2023 ### 10/10 Excellent #### Wendy O., Annapolis Oct 11, 2020 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Lovely home in beautiful part of Chincoteague. This unit had everything to make our stay comfortable. We spent almost all our time on the screened in porch. There was a well stocked kitchen with all the necessary appliances. The house was extremely clean. A must with all that is going on now. Would return if I ever get back to Chincoteague. ##### Wendy O. 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