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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

Dining
Interior
Exterior
Outdoor dining
Fridge, microwave, oven, stovetop

Reviews

9.2 out of 10
Wonderful

Entire home

3 bedrooms2 bathroomsSleeps 81680 sq ft

Popular amenities

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

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

Waterfront holiday home with kitchen and balcony
A water park, laundry facilities and a garden are available at this smoke-free holiday home. Other amenities include barbecues. The holiday home has 3 bedrooms and offers free WiFi and a balcony. Guests will find a kitchen with a fridge, an oven, a stovetop and a microwave.
Air-conditioned accommodation at this holiday home offers coffee/tea makers and an iron/ironing board. Rooms open to balconies or patios. Kitchens offer fridges, stovetops, microwaves and kitchenware and utensils. Bathrooms include baths or showers.

Guests can surf the web using complimentary wireless Internet access. Flat-screen televisions come with cable channels.

Recreational amenities at the holiday home include a water park.

Property manager

Seaside Vacations & Sales

Languages

English

Add dates for prices

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

  • Laundry facilities
  • 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

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  • Washer
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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

Pets not allowed

Children and extra beds

Children are welcome

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 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

Property is also known as

150425

About the area

Map
Chincoteague Island, VA

What's nearby

  • Oyster Bay - 9 min walk - 0.8 km
  • Captain Timothy Hill House - 5 min drive - 2.8 km
  • Maui Jack's Waterpark - 5 min drive - 3.1 km
  • Robert N. Reed Downtown Waterfront Park - 6 min drive - 3.9 km
  • Museum of Chincoteague - 7 min drive - 3.8 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).

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

Reviews

9.2

Wonderful

Rating 10 - Excellent. 35 out of 46 reviews
Rating 8 - Good. 6 out of 46 reviews
Rating 6 - Okay. 3 out of 46 reviews
Rating 4 - Poor. 1 out of 46 reviews
Rating 2 - Terrible. 1 out of 46 reviews

8.8/10

Cleanliness

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

Wendy O., Annapolis

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

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

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

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

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

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

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