Entire home

Smooth Sailing by Seaside Vacations & Sales

Photo gallery for Smooth Sailing by Seaside Vacations & Sales

A room with a large skylight, a wooden ceiling beam, a television, a blue sofa, a wooden table, and a hanging light fixture.
A spacious living room with a blue sectional sofa, a wooden coffee table, and a patterned rug.
A covered porch with wooden furniture, a table, and a view of houses and trees.
A two-story wooden house with a balcony and a slide leading to the main building.
A spacious living room with a large blue sectional sofa, a wooden coffee table, and a ceiling fan.

Reviews

9.4 out of 10
Exceptional

Highlights

  • Family fun awaits
    Top-rated for families.
  • Private garden
    A rare find — relax in the peaceful, private garden space.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Near Oyster Bay

Popular amenities

  • Balcony or patio
  • Waterpark access
  • Barbecue grill
  • Free internet
  • Air-conditioning
  • Washing machine

Explore the area

View in a map
Chincoteague Island, VA
  • Place, Oyster Bay
    ‪9 min walk‬
  • Place, Chincoteague National Wildlife Refuge
    ‪8 min drive‬
  • Place, Assateague Lighthouse
    ‪10 min drive‬
  • Airport, Ocean City, MD (OCE-Ocean City Municipal)
    ‪87 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

Add dates for prices

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About the area

Chincoteague

Located on the waterfront, this holiday home is in Deep Hole, a neighbourhood in Chincoteague. Captain Timothy Hill House and Assateague Lighthouse are local landmarks, and the area's natural beauty can be seen at Oyster Bay and Chincoteague Channel. 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.
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Map
Chincoteague Island, VA

What's nearby

  • Oyster Bay - 9 min walk - 0.8 km
  • Maui Jack's Waterpark - 5 min drive - 4.5 km
  • beach near Downtown Chincoteague - 7 min drive - 5.9 km
  • Chincoteague National Wildlife Refuge - 8 min drive - 6.2 km
  • Assateague Lighthouse - 10 min drive - 7.5 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
  • ‪Captain Zack's Seafood - ‬3 min drive
  • ‪Asian Express - ‬5 min drive

Frequently asked questions

Is Smooth Sailing by Seaside Vacations & Sales pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Smooth Sailing by Seaside Vacations & Sales?

As of 25 Oct 2026, prices found for a 1-night stay for 2 adults at Smooth Sailing by Seaside Vacations & Sales on 15 Nov 2026 start from £720, 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 by Seaside Vacations & Sales?

On-site parking is available at the property.

What time is check-in at Smooth Sailing by Seaside Vacations & Sales?

Check-in begins at 4:00 PM.

What time is check-out at Smooth Sailing by Seaside Vacations & Sales?

Checkout is at 10:00 AM.

Where is Smooth Sailing by Seaside Vacations & Sales 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 Chincoteague Channel and Maui Jack's Waterpark. Captain Timothy Hill House and Robert N. Reed Downtown Waterfront Park are also within 3 miles (5 km).

Reviews

9.4

Exceptional

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. 43 out of 54 reviews
Rating 8 - Good. 6 out of 54 reviews
Rating 6 - Okay. 3 out of 54 reviews
Rating 4 - Poor. 1 out of 54 reviews
Rating 2 - Terrible. 1 out of 54 reviews

8.8/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great stay! Waking up to views of the water, having access to kayaks and beach chairs, it was a perfect getaway location. Thanks for hosting us.
Stayed 5 nights in Jun 2026
Response from VrboOwner on 16 Jun 2026
We're so glad to hear you enjoyed your time at Smooth Sailing, Marta! This home truly is a water lover's paradise! We'd love to have you back anytime!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Property had everything we needed to cook and have an organized family outing. Great location.
Stayed 4 nights in May 2026
Response from VrboOwner on 25 May 2026
We're so glad to hear your family enjoyed its time at Smooth Sailing, Randy! We hope to have you all back soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved staying here. This is our second time staying with this company and we have never been disappointed. The house was clean and beautiful! We would definitely consider this location for our future trips!
Stayed 3 nights in May 2026
Response from VrboOwner on 3 Jun 2026
We're so happy to hear you've enjoyed your experience with Seaside Vacations, Keleigh! Hope to have you all back soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place! Well equipped!
Stayed 3 nights in Apr 2026
Response from VrboOwner on 15 Apr 2026
We're so glad to hear you enjoyed your time at Smooth Sailing, Sarah! Thanks so much for allowing Seaside Vacations to be a part of your getaway. We hope to have you back soon!
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home. Quiet location. Great community for peaceful walks
Stayed 4 nights in Mar 2026
Response from VrboOwner on 15 Apr 2026
Thanks again for choosing to stay with Seaside Vacations, Sarah! We're so glad to hear you enjoyed your time with us, and hope to have you back soon!
Verified review

10/10 Excellent

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 Sept 2024
Thanks so much for allowing Seaside Vacations to be a part of your getaway! We hope to have you back soon!
Verified review

10/10 Excellent

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 Jul 2020
Hi Howard! We are so happy you enjoyed Smooth Sailing! :) Best, Lea Anna
Verified review

10/10 Excellent

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 Sept 2021
So happy you enjoyed your stay, Thomas - thank you for staying with Seaside Vacations! Best, Elaine, Owner
Verified review

10/10 Excellent

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 Oct 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 review

10/10 Excellent

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 Jul 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 review

10/10 Excellent

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 Apr 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 review

10/10 Excellent

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 review

10/10 Excellent

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 Jun 2024
Thanks so much for choosing to stay with us, Martin! We hope to have you back (with some better weather!)
Verified review

10/10 Excellent

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 Sept 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 review

10/10 Excellent

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 review

10/10 Excellent

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 Jul 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 review

10/10 Excellent

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

Great

Nice getaway.
Stayed 3 nights in Oct 2023
Response from VrboOwner on 30 Oct 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 review

10/10 Excellent

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 Mar 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 review

8/10 Good

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 Dec 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 review

8/10 Good

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 Mar 2021
Julie, So happy you enjoyed the house . A bike is the best way to get around. Come visit again! Best, Lynn
Verified review

10/10 Excellent

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 Jun 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 review

10/10 Excellent

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 Sept 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 review

10/10 Excellent

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 Apr 2023
Charles, you were an absolute joy to host. We hope to have you back soon! :)
Verified review

10/10 Excellent

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 Feb 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 review

10/10 Excellent

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 Nov 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! :)
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