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 Waterfront vacation home with kitchen and balcony ![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) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32710000/32702800/32702731/42289cdc.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) - 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 ## Similar properties ![Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils](https://images.trvl-media.com/lodging/32000000/31870000/31861900/31861806/bf0a15b3.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Make fabulous Vacation Memories at Family Tides Vacation Rental on Chincoteague Chincoteague Island - Kitchen - Washer - Free WiFi - Air conditioning 9.8 Exceptional 53 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-19&endDate=2025-11-20&selected=31861806&PinnedHotelID=31861806&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/32000000/31900000/31895600/31895598/a56462c8.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### To the Lighthouse (formerly Epiphany) is a breathtaking 3 Bedroom/3 Full Bath Va Birch Town - Kitchen - Washer - Dryer - Free WiFi 9.6 Exceptional 64 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-19&endDate=2025-11-20&selected=31895598&PinnedHotelID=31895598&HadPinnedHotel=true®ionId=-1&adults=2) ![Smart TV](https://images.trvl-media.com/lodging/72000000/71920000/71918000/71917908/fec2741c.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Island Sunset on Chincoteague Island - Bayfront with Private Pier! 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Snotty Ridge - Kitchen - Washer - Dryer - Free WiFi 10 Exceptional 155 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-11-19&endDate=2025-11-20&selected=35095095&PinnedHotelID=35095095&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 ### 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 ![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 - ‪Island Creamery - ‬4 min drive - ‪McDonald's - ‬6 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? > Located in Deep Hole, 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. Ask a question ## Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst Reviews 9.2 ### 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) ### 8.8 Cleanliness ### 9.8 Location 10 - Excellent 36 8 - Good 6 6 - Okay 3 4 - Poor 1 2 - Terrible 1 ### 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 #### 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 #### 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 #### 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 ### 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 #### 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 ### 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 #### Theresa R. Jul 1, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Beautiful spot on the canal 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! ##### Theresa R. Stayed 7 nights in Jun 2023 ### 8/10 Good #### Ellen W. Aug 10, 2020 Liked: Check-in, communication, location, listing accuracy Disliked: Cleanliness #### Family Vacation at Smooth Sailing Great home Great Location LOve having the beach chairs , boards and bikes . Cleaning could have been better . Cobwebs on kitchen light and ran sweeper first day with lots of sand and hair on family room floor because we have crawling baby. Some lights without light bulbs . Need a dutch oven pot , only had big crab pot so need two bigger pots. No measuring cups in kitchen . But still great place !! Thanks ##### Ellen W. Stayed 7 nights in Aug 2020 ### 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 ### 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 #### 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 #### 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 #### 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 #### 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 ### 6/10 Okay #### maxine N. Jun 6, 2023 Liked: Check-in, communication, location Disliked: Cleanliness #### Maintenance The property’s exterior wasn’t kept up. Holes in screens, spider webs and debris stuck in screens, decks and walkways not swept, window cranks broken. Excellent location ##### maxine N. Stayed 3 nights in Jun 2023 ### 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 #### 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 #### 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 ### 6/10 Okay #### Debby P. Sep 5, 2022 Liked: Check-in, communication, location, listing accuracy Disliked: Cleanliness #### Needs improvements Needs a deep clean and updated porch and deck. Holey screens and spaces in porch floor are not good for protection from mosquitoes! ##### Debby P. Stayed 7 nights in Aug 2022 ### 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 #### amanda f. Nov 12, 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Perfect quiet anniversary getaway Everything was perfect. Huge fan of auto checkin with getting the door code messaged to me days before. House was clean and well maintained. Well equipped full sized kitchen had everything needed to make daily meals. Very comfortable living room for lounging. All bedrooms were big, and 2 full bathrooms. Plenty of parking in easy to find location. Very quiet and peaceful neighborhood, which is exactly what I wanted. ##### amanda f. Stayed 4 nights in Nov 2021 ### 10/10 Excellent #### Mark and Karyn B. Oct 25, 2021 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Perfect family reunion We're local but had our sons come with their wives for a week together. One set came all the way from the Seattle area. Lots of seating options for 6 adults, great kitchen for group meals or diy breakfast and lunch. Loved the view of the canal and great neighborhood for taking a walk. We'd stay there again for sure. ##### Mark and Karyn B. Stayed 6 nights in Oct 2021 ### 4/10 Poor #### Sandra D., Hamburg, New Jersey Sep 25, 2021 Liked: Check-in, communication, location #### TLC Well equipped home, beautifully decorated but needs TLC in areas…housekeeping can take care of cobwebs and dust bunnies..homeowners should leave instructions on operating tv, etc.. ##### Sandra D. Stayed 7 nights in Sep 2021 ### 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. 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