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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

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Explore the area

View map
Chincoteague Island, VA
  • Place, Oyster Bay
    ‪9 min walk‬
  • Place, Ocean City Boardwalk
  • Place, Ocean City Beach
  • Airport, Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)
    ‪68 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
Porch or lanai
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.

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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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

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 does it cost to stay at Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst?

As of 6 April 2026, prices found for a 1-night stay for 2 adults at Smooth Sailing is a fabulous Direct Canalfront Vacation Home in prestigious Oyst on 29 May 2026 start from NZ$459, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

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

Verified

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
Response from VrboOwner on 6 October 2025
We're so glad to hear you enjoyed your time at Smooth Sailing, Jeff! Thanks so much for allowing Seaside Vacations to be a part of your getaway, and we hope to have you back soon! Best, Tim
Verified

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
Response from VrboOwner on 30 September 2024
Thanks so much for allowing Seaside Vacations to be a part of your getaway! We hope to have you back soon!
Verified

10/10 Excellent

Howard W.

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

Great weekend getaway

Clean and good location and we met some friendly neighbors!
Stayed 3 nights in May 2020
Response from VrboOwner on 7 July 2020
Hi Howard! We are so happy you enjoyed Smooth Sailing! :) Best, Lea Anna
Verified

10/10 Excellent

Thomas C.

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
Response from VrboOwner on 11 September 2021
So happy you enjoyed your stay, Thomas - thank you for staying with Seaside Vacations! Best, Elaine, Owner
Verified

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
Response from VrboOwner on 21 May 2025
Hey there, Jeffery! So happy to hear that you were pleased with the property and the service! We hope that you had a lovely vacation and that you come back and visit again soon!
Verified

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
Response from VrboOwner on 1 July 2024
Thanks so much for choosing to stay with Seaside Vacations, Ralph! We're so glad you enjoyed your stay at Smooth Sailing and hope to have you back soon!
Verified

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
Response from VrboOwner on 22 April 2024
Thanks so much for choosing to stay with Seaside Vacations, Sean! We're so glad you enjoyed your visit, and hope to have you back soon!
Verified

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
Response from VrboOwner on 20 May 2024
Hi, Alexandr! Thank you so much for taking the time to leave us a review! We are so glad that you enjoyed calling Smooth Sailing your home during your stay, and hope to have you back soon!
Verified

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
Response from VrboOwner on 23 June 2024
Thanks so much for choosing to stay with us, Martin! We hope to have you back (with some better weather!)
Verified

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
Response from VrboOwner on 26 September 2023
We're so glad you enjoyed your stay, Lisa! Smooth Sailing's location is so peaceful! We hope to have you back soon! :) Please feel free to reach out the next time you're planning to visit the area! We offer Repeat Guest discounts and can save you money on fees! :)
Verified

10/10 Excellent

Erin B.

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
Response from VrboOwner on 24 July 2023
Thanks so much for choosing to stay with us, Erin! We're so glad to have been a part of you family's vacation, and hope to have you all back next year!
Verified

10/10 Excellent

Robert V.

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

Great

Nice getaway.
Stayed 3 nights in Oct 2023
Response from VrboOwner on 30 October 2023
Thanks so much for choosing to stay with us, Robert! We're so glad you enjoyed your stay, and hope to have you back soon!
Verified

10/10 Excellent

Alexandra H.

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

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
Response from VrboOwner on 30 March 2021
Alexandra, We are so glad you had a chance to get away and relax. There is nothing better! Come back and visit when you have more time. Best, Lynn
Verified

8/10 Good

Jemma L.

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

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.
Stayed 3 nights in Dec 2020
Response from VrboOwner on 30 December 2020
Hi there! So happy to hear you enjoyed your time at Smooth Sailing! The views are amazing! :) We would love to have you and your family again! Best, Lea Anna ~ Seaside Vacations
Verified

8/10 Good

Julie M.

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

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.
Stayed 3 nights in Mar 2021
Response from VrboOwner on 30 March 2021
Julie, So happy you enjoyed the house . A bike is the best way to get around. Come visit again! Best, Lynn
Verified

10/10 Excellent

Cheri H.

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
Response from VrboOwner on 30 June 2023
Thanks so much for choosing to stay with us again, David! So glad you enjoyed your stay, and we hope to have you back again soon! :)
Verified

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
Response from VrboOwner on 1 September 2022
Steve, Thank you for the 5 star review! We are happy you enjoyed the home and the service we provided! Please visit us again. Best, Lynn with Seaside Vacations
Verified

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
Response from VrboOwner on 25 October 2020
Hi Pamela, so happy you had a great stay! I wasn't aware of any cleaning issues at the house? Happy to chat anytime - 757.336.7070. If you had any issues, I definitely want to know about them. Best, Elaine
Verified

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
Response from VrboOwner on 25 April 2023
Charles, you were an absolute joy to host. We hope to have you back soon! :)
Verified

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
Response from VrboOwner on 2 February 2024
Thanks so much for choosing to stay with us, Anastasia! We're so glad your family enjoyed its stay and those amazing views from the home! Hope to have you back soon!
Verified

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
Response from VrboOwner on 28 November 2022
Thanks so much for choosing to stay with us, Jessica! We're so glad you enjoyed your visit to Smooth Sailing and hope to have you back! :)
Verified

10/10 Excellent

William A.

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

Great spot in a nice neighborhood on Chincoteague Island

Great place on a great island. Check in process was a little frustrating because I never received the welcome email with the relevant info, but a call to the after-hours line and a short 5-10 minute wait on the patio, and we were in with no additional problems. Would recommend to anyone looking to get away to this great ocean/bay side community. Also, Gary Howard's Seafood is really close to the rental and has the best fresh seafood in town! Highly recommend!
Stayed 3 nights in Jun 2020
Response from VrboOwner on 6 July 2020
Hi William! So happy you enjoyed Smooth Sailing! :) Please come back and see us again! Best, Lea Anna ~ Seaside Vacations
Verified

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
Response from VrboOwner on 12 May 2023
Thanks so much for choosing to stay with us, Diane! We're so glad you all enjoyed your stay at Smooth Sailing! We hope to have you back soon! :) The canal will be waiting for you and your kayaks!
Verified

10/10 Excellent

Wendy O.

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

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.
Stayed 3 nights in Sep 2020
Response from VrboOwner on 13 October 2020
Hi Wendy! We'd love to have you again at Smooth Sailing! So happy you enjoyed it as much as you did! :) Best, Lea Anna
Verified

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
Response from VrboOwner on 15 November 2021
Amanda, Thank you for the five star review! We appreciate the wonderful things you said. Please visit again, we look forward to it. Best, Lynn

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