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

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Welcome to Smooth Sailing on beautiful Chincoteague Island.
Soaring Ceilings and a Wall of Windows to the Water!
Spectacular Water Views in every direction!
Fish and Kayak in your own backyard, or bring the Boat!
This breathtaking Vacation Home is located in very desirable Oyster Bay.

Reviews

9.2 out of 10
Wonderful
3 bedrooms2 bathroomsSleeps 8156.1 sq m

Popular amenities

  • Dryer
  • Parking available
  • Washer
  • Kitchen
  • Barbecue grill
  • Free WiFi

Explore the area

Map
Chincoteague Island, VA
  • Oyster Bay
    ‪9 min walk‬
  • Robert N. Reed Downtown Waterfront Park
    ‪5 min drive‬
  • Maui Jack's Waterpark
    ‪5 min drive‬
  • Ocean City, MD (OCE-Ocean City Municipal)
    ‪76 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.

Property manager

Seaside Vacations & Sales
Premier Host

Languages

English

Add dates for prices

Amenities

Kitchen
Washer
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
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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.
Map
Chincoteague Island, VA

What's nearby

  • Oyster Bay - 9 min walk - 0.8 km
  • Robert N. Reed Downtown Waterfront Park - 5 min drive - 3.6 km
  • Maui Jack's Waterpark - 5 min drive - 3.1 km
  • Captain Timothy Hill House - 6 min drive - 3.3 km
  • Museum of Chincoteague - 6 min drive - 3.7 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
  • ‪Famous Pizza & Sub Shoppe - ‬5 min drive
  • ‪Mister Whippy - ‬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?

Checkout is at 10:00 AM.

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

Situated on the waterfront, this holiday home is 0.4 mi (0.7 km) from Oyster Bay and within 3 miles (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 miles (5 km).

Reviews

9.2

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 34 out of 45 reviews
Rating 8 - Good. 6 out of 45 reviews
Rating 6 - Okay. 3 out of 45 reviews
Rating 4 - Poor. 1 out of 45 reviews
Rating 2 - Terrible. 1 out of 45 reviews

8.8/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

8/10 Good

Tessa E.

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.
Stayed 6 nights in Mar 2025

10/10 Excellent

Heidi C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great vacation

It was a great location with all the amenities
Stayed 7 nights in Sep 2024

10/10 Excellent

Verified traveller

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.
Stayed 4 nights in Mar 2024

10/10 Excellent

Ralph A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Chinco Vacay

Great location, lots of amenities.
Stayed 7 nights in Jun 2024

10/10 Excellent

Sean B.

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.
Stayed 4 nights in Mar 2024

10/10 Excellent

Anastasia K.

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!
Stayed 7 nights in Dec 2023

10/10 Excellent

Robert V., Boulder, CO USA

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great

Nice getaway.
Stayed 3 nights in Oct 2023

10/10 Excellent

Lisa G.

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.
Stayed 7 nights in Sep 2023

10/10 Excellent

Theresa R.

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!
Stayed 7 nights in Jun 2023

10/10 Excellent

Cheri H., Mercer, PA

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!
Stayed 7 nights in Jun 2023

10/10 Excellent

Erin B., Kutztown, PA, USA

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.
Stayed 6 nights in Jun 2023

6/10 Okay

maxine N.

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
Stayed 3 nights in Jun 2023

10/10 Excellent

Diane J.

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!
Stayed 3 nights in May 2023

10/10 Excellent

charles b.

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
Stayed 6 nights in Apr 2023

10/10 Excellent

Alex C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent property!

Everything as described! Will come again!!!
Stayed 4 nights in May 2022

10/10 Excellent

Jessica M.

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 !
Stayed 3 nights in Nov 2022

6/10 Okay

Debby P.

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!
Stayed 7 nights in Aug 2022

10/10 Excellent

Steve D.

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
Stayed 7 nights in Aug 2022

10/10 Excellent

amanda f.

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.
Stayed 4 nights in Nov 2021

10/10 Excellent

Mark and Karyn B.

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.
Stayed 6 nights in Oct 2021

4/10 Poor

Sandra D., Hamburg, New Jersey

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..
Stayed 7 nights in Sep 2021

10/10 Excellent

Thomas C., Alexandria, VA

Liked: Cleanliness, check-in, communication, location, listing accuracy

Chincoteague vacation

Nice, quiet setting with all the amenities we needed.
Stayed 7 nights in Aug 2021

6/10 Okay

Brian S.

Liked: Check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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, check-in, communication, location, listing accuracy

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

About the host

Hosted by Seaside Vacations & Sales

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Languages:

English

Premier Host

They consistently provide great experiences for their guests