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Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst

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your current months are January, 2025 and February, 2025.
January 2025
February 2025

Reviews

9.2 out of 10

Wonderful

Entire home

3 bedrooms2 bathroomsSleeps 8156 sq m

Popular amenities

  • Parking available
  • Washer
  • Barbecue grill
  • Air conditioning
  • Kitchen
  • Dryer

Explore the area

Map
Chincoteague Island, VA
  • Oyster Bay
    9 min walk
  • Gary Howard Seafood
    12 min walk
  • Ocean City Station
    75 min drive
  • Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)
    67 min drive

Room options

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.
During your stay at this holiday home, you're just a quick walk from Oyster Bay. You'll find features such as a water park. The holiday home offers free WiFi and a kitchen.
  • Air-conditioned home with kitchen, washing machine and 2 bathrooms
  • Free WiFi
  • Splash around at the water park
  • 9 minutes on foot from Oyster Bay and a 5-minute drive from Chincoteague Channel
Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst offers its guests a water park. Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst also features barbecue grills and a garden.

Property manager

Seaside Vacations & Sales

Languages

English

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • 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

  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

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

  • No pets allowed

Children and extra beds

  • Children are welcome.

Important information

You need to know

This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account, which will enable you to manage your booking.

Property is also known as

150425

Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst Reviews

Reviews

9.2

Wonderful

Rating 10 - Excellent. 34 out of 44 reviews" "
Rating 8 - Good. 5 out of 44 reviews" "
Rating 6 - Okay. 3 out of 44 reviews" "
Rating 4 - Poor. 1 out of 44 reviews" "
Rating 2 - Terrible. 1 out of 44 reviews" "

8.8/10

Cleanliness

Reviews

10/10 Excellent

Heidi C.

Liked: Cleanliness
Great vacation
It was a great location with all the amenities
Stayed 7 nights in Sep 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness
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.
Stayed 4 nights in Mar 2024

10/10 Excellent

Ralph A.

Liked: Cleanliness
Chinco Vacay
Great location, lots of amenities.
Stayed 7 nights in Jun 2024

10/10 Excellent

Sean B.

Liked: Cleanliness
First time visiting Chincoteague
Great location right on the water for kayaking and paddle boarding. Short drive to downtown and the Wildlife Refuge.
Stayed 4 nights in Mar 2024

10/10 Excellent

Anastasia K.

Liked: Cleanliness
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!
Stayed 7 nights in Dec 2023

10/10 Excellent

Robert V., Boulder, CO USA

Liked: Cleanliness
Great
Nice getaway.
Stayed 3 nights in Oct 2023

10/10 Excellent

Lisa G.

Liked: Cleanliness
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.
Stayed 7 nights in Sep 2023

10/10 Excellent

Theresa R.

Liked: Cleanliness
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!
Stayed 7 nights in Jun 2023

10/10 Excellent

Cheri H., Mercer, PA

Liked: Cleanliness
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!
Stayed 7 nights in Jun 2023

10/10 Excellent

Erin B., Kutztown, PA, USA

Liked: Cleanliness
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.
Stayed 6 nights in Jun 2023

6/10 Okay

maxine N.

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
Stayed 3 nights in Jun 2023

10/10 Excellent

Diane J.

Liked: Cleanliness
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!
Stayed 3 nights in May 2023

10/10 Excellent

charles b.

Liked: Cleanliness
Smooth sailing
Was definitely one of best experiences ever thank you for the wonderful customer service and will definitely be doing business again soon
Stayed 6 nights in Apr 2023

10/10 Excellent

Alex C., Schaumburg, Illinois

Liked: Cleanliness
Excellent property!
Everything as described! Will come again!!!
Stayed 4 nights in May 2022

10/10 Excellent

Jessica M.

Liked: Cleanliness
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 !
Stayed 3 nights in Nov 2022

6/10 Okay

Debby P.

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!
Stayed 7 nights in Aug 2022

10/10 Excellent

Steve D.

Liked: Cleanliness
First time VRBO user very satisfied.
Everything in the house worked. Communication was good and there were issues during our stay
Stayed 7 nights in Aug 2022

10/10 Excellent

amanda f.

Liked: Cleanliness
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.
Stayed 4 nights in Nov 2021

10/10 Excellent

Mark and Karyn B.

Liked: Cleanliness
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.
Stayed 6 nights in Oct 2021

4/10 Poor

Sandra D., Hamburg, New Jersey

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..
Stayed 7 nights in Sep 2021

10/10 Excellent

Thomas C., Alexandria, VA

Liked: Cleanliness
Chincoteague vacation
Nice, quiet setting with all the amenities we needed.
Stayed 7 nights in Aug 2021

6/10 Okay

Brian S.

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.
Stayed 5 nights in Apr 2021

10/10 Excellent

Kristen T.

Liked: Cleanliness
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!"
Stayed 3 nights in Apr 2021

10/10 Excellent

Roman G.

Liked: Cleanliness
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!
Stayed 7 nights in Mar 2021

10/10 Excellent

Alexandra H.

Liked: Cleanliness
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.
Stayed 5 nights in Mar 2021