Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst
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.
"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
Reviews
4.6
Outstanding(44 Reviews)4.6
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.
4.6
Great location, lots of amenities.
4.6
Great location right on the water for kayaking and paddle boarding. Short drive to downtown and the Wildlife Refuge.
4.6
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!
4.6
Nice getaway.
4.6
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.
4.6
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!
4.6
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!
4.6
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.
4.6
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
4.6
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!
4.6
Was definitely one of best experiences ever thank you for the wonderful customer service and will definitely be doing business again soon
4.6
Everything as described!
Will come again!!!
4.6
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 !
4.6
Needs a deep clean and updated porch and deck. Holey screens and spaces in porch floor are not good for protection from mosquitoes!
4.6
Everything in the house worked. Communication was good and there were issues during our stay
4.6
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.
4.6
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.
4.6
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..
4.6
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..
4.6
Chincoteague vacation
Nice, quiet setting with all the amenities we needed.
4.6
Great location, not so great cleanliness
Amazing location, right on the water with easy access to kayak, fish, relax by the canal. About 5 minute drive from everything and 10min drive from Assateague national park. Unfortunately, the property cleanliness leaves much to be desired. The floors were filthy when we arrived (with 2 young children who were on the floor a lot) and we contacted the management group about it. They sent someone out the next day to reclean floors but there was barely any improvement. Visible dust bunnies and lint in upstairs master. Additionally, there were cobwebs in every corner of the house, visible grime on the kitchen cabinets, stains on loveseat in living area. Everything just needs a major overhaul and deep cleaning, and it is clear that the professional cleaning done between guests is very surface level and rushed. Luckily we did not spend much time in the home with the exception of the outdoors.
4.6
We truly loved our getaway
We really enjoyed our visit. We utilized the kayaks and enjoyed the quick ride into town and over to Assateague. It was a wonderful getaway and the house had beautiful views with its full glass windows. The swing was a delight as well. The neighborhood was quiet and my kids truly enjoyed "their vacation home!"
4.6
Great time!
The property is fantastically located and very clean. We loved grilling and kayaking and spending a nice quite spring break with our family. Highly recommend this place!
4.6
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.
4.6
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.
4.6
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.
4.6
Everything we were looking for
We had a lovely stay at Smooth Sailing. Being on the water was a real draw. We took the kayaks out each day - so easy to do from the dock. We also enjoyed the bikes. Most of all, the home is very comfortable with great views of the channel out of the huge windows. We went to Assateague Island for hiking each day and were rewarded with plenty of pony sightings. Some nights we cooked in and others we ordered excellent take out meals from Cosa Pizza food truck and Ropewalk. Easy, friendly and prompt communication with the rental staff. We will recommend this home to friends and hope to be back!
4.6
We enjoyed our time at Smooth Sailing. The house was as described. Located in a neighborhood where it was easy to walk or run around. We enjoyed relaxing at the house and watching the birds outside. It was a short drive to the entrance of the Chincoteague National Wildlife Refuge.It looks like the outdoor amenities (bikes, kayaks) would be great to use. The house had a few quirks (like a shower door that didn't want to stay closed), but no significant items. My children really enjoyed the books and kids that were available in one of the closets. Overall, we would stay here again if we were in the area.
4.6
Great family getaway
We enjoyed our time at Smooth Sailing. The house was as described. Located in a neighborhood where it was easy to walk or run around. We enjoyed relaxing at the house and watching the birds outside. It was a short drive to the entrance of the Chincoteague National Wildlife Refuge.
It looks like the outdoor amenities (bikes, kayaks) would be great to use. The house had a few quirks (like a shower door that didn't want to stay closed), but no significant items. My children really enjoyed the books and kids that were available in one of the closets. Overall, we would stay here again if we were in the area.
4.6
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.
4.6
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.
4.6
We stayed at this house for 2 weeks in October. My daughter and myself spent many hours cleaning this home before we felt comfortable. This home is in need of a deep cleaning as well as needing upgrades, repairs, and general maintaining. As a property owner of several homes I would not rent this home to people in this condition. It appears the owners are not actively involved in making sure this house is deep cleaned, maintained and repaired. Here are a few of the issues we encounered: doors, walls and door frames were dirty, hole in tub, carpets were musty, dirty and had a wet dog smell. Dirty air vents and kitchen chairs..stained upholstry on couches, kitchen counter separating from wall, clogged drains and 2 vacumn cleaners that did not work.Shower donstairs had a huge hole that someone chalked and clogged the drain when the pieces came out as well as the floor boards under the shower making noises when you stood in it.. I suspect there will be major water damage if not soon corrected,.Matresses were old, worn and musty smelling.
4.6
Review of Smooth Sailing Property
We stayed at this house for 2 weeks in October. My daughter and myself spent many hours cleaning this home before we felt comfortable. This home is in need of a deep cleaning as well as needing upgrades, repairs, and general maintaining. As a property owner of several homes I would not rent this home to people in this condition. It appears the owners are not actively involved in making sure this house is deep cleaned, maintained and repaired. Here are a few of the issues we encounered: doors, walls and door frames were dirty, hole in tub, carpets were musty, dirty and had a wet dog smell. Dirty air vents and kitchen chairs..stained upholstry on couches, kitchen counter separating from wall, clogged drains and 2 vacumn cleaners that did not work.Shower donstairs had a huge hole that someone chalked and clogged the drain when the pieces came out as well as the floor boards under the shower making noises when you stood in it.. I suspect there will be major water damage if not soon corrected,.Matresses were old, worn and musty smelling.
4.6
This setting is a perfect place to relax The entire environment was comfortably laidback. This is what we wanted. However, if you are looking for fishing, kayaking, or bicycling - that is there too!
4.6
Serene and Peaceful
This setting is a perfect place to relax The entire environment was comfortably laidback. This is what we wanted. However, if you are looking for fishing, kayaking, or bicycling - that is there too!
4.6
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.
4.6
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.
4.6
Great spot in Chincoteague!
Very peaceful setting on the canal. The house was very comfortable. Wish we could have stayed longer.
4.6
the property is great downstairs and the deck is fab. the upstairs bedroom is not very inviting and the bathroom there, is too samll with little space to put a guest's bathroom stuff. We opted for the king bed thinking the bedroom itself would be more of a 'master' bedroom, but should have chosen the quenn downstairs.
FAQs
How much does this house cost compared to others in Chincoteague Island?
The average price for a rental in Chincoteague Island is $237 per night. This rental is $12 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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Garden · Pool · Kitchen or Kitchenette
This House in Chincoteague Island, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
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Laughing Pony - Renovated, in town, patio! LINENS AND TOWELS PROVIDED
House
in Chincoteague10 guests · 4 bedrooms · 2 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi
When traveling to Chincoteague Island, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $239 per night.
$$$$
Sundance - In town; Screened porch!
House
in Chincoteague Island9 guests · 4 bedrooms · 3 baths
Pool · Kitchen or Kitchenette · Air conditioner
Looking for a memorable stay in Chincoteague Island? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.
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