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

Waterfront holiday home with kitchen and balcony

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

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

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Barbecue grill
  • Kitchen
  • Outdoor space

Explore the area

View map
Chincoteague Island, VA
  • Place, Oyster Bay
    ‪9 min walk‬
  • Place, Maui Jack's Waterpark
    ‪4 min drive‬
  • Place, Robert N. Reed Downtown Waterfront Park
    ‪5 min drive‬
  • Airport, Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)
    ‪68 min drive‬

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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.

How much is parking at Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst?

On-site parking is available at the 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?

Located in Deep Hole, 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. 36 out of 47 reviews
Rating 8 - Good. 6 out of 47 reviews
Rating 6 - Okay. 3 out of 47 reviews
Rating 4 - Poor. 1 out of 47 reviews
Rating 2 - Terrible. 1 out of 47 reviews

8.8/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

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

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

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

Pamela F.

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!
Stayed 7 nights in Jul 2020

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

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

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

8/10 Good

Ellen W.

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
Stayed 7 nights in Aug 2020

10/10 Excellent

Jeff S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
House is very well equipped for cooking and entertainment
Stayed 3 nights in Sep 2025

10/10 Excellent

Jeffrey M.

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.
Stayed 7 nights in May 2025

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

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

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

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

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
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