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





Reviews
9.2 out of 10
Wonderful
3 bedrooms2 bathroomsSleeps 8156.1 sq m
Popular amenities
Explore the area

Chincoteague Island, VA
- Place, Oyster Bay9 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
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space
Have a question?
Get instant answers with AI powered search of property information and reviews.
Similar properties

Make fabulous Vacation Memories at Family Tides Vacation Rental on Chincoteague
Make fabulous Vacation Memories at Family Tides Vacation Rental on Chincoteague
- Kitchen
- Washing machine
- Free Wi-Fi
- Air-conditioning
9.8 out of 10, Exceptional, (53 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
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
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 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.

Chincoteague Island, VA
What's nearby
- Oyster Bay - 9 min walk - 0.8 km
- Maui Jack's Waterpark - 4 min drive - 3.1 km
- Robert N. Reed Downtown Waterfront Park - 5 min drive - 3.9 km
- Chincoteague National Wildlife Refuge - 6 min drive - 4.5 km
- Assateague Lighthouse - 9 min drive - 6.2 km
Getting around
Restaurants
- Island Creamery - 4 min drive
- McDonald's - 6 min drive
- Steamers - 4 min drive
- Famous Pizza & Sub Shoppe - 5 min drive
- Teaguers - 3 min drive
Frequently asked questions
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 window8.8/10
Cleanliness
9.8/10
Check-in
9.8/10
Communication
10/10
Location
9.6/10
Listing accuracy
Reviews
Verified
5 Oct 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Sep 2025
Verified
10/10 Excellent
Heidi C.
28 Sept 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great vacation
Heidi C.
Stayed 7 nights in Sep 2024
Verified
10/10 Excellent
Howard W.
22 June 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great weekend getaway
Howard W.
Stayed 3 nights in May 2020
Verified
10/10 Excellent
Thomas C.
11 Sept 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Chincoteague vacation
Thomas C.
Stayed 7 nights in Aug 2021
Verified
10/10 Excellent
Jeffrey M.
19 May 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
No regrets
Jeffrey M.
Stayed 7 nights in May 2025
Verified
10/10 Excellent
Ralph A.
15 June 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Chinco Vacay
Ralph A.
Stayed 7 nights in Jun 2024
Verified
10/10 Excellent
Sean B.
4 Apr 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
First time visiting Chincoteague
Sean B.
Stayed 4 nights in Mar 2024
Verified
10/10 Excellent
Alex C.
31 Jan 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent property!
Alex C.
Stayed 4 nights in May 2022
Verified
10/10 Excellent
Verified traveller
22 June 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful home and location.
Verified traveller
Stayed 4 nights in Mar 2024
Verified
10/10 Excellent
Lisa G.
25 Sept 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful
Lisa G.
Stayed 7 nights in Sep 2023
Verified
10/10 Excellent
Erin B.
12 June 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great for family
Erin B.
Stayed 6 nights in Jun 2023
Verified
10/10 Excellent
Robert V.
29 Oct 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great
Robert V.
Stayed 3 nights in Oct 2023
Verified
10/10 Excellent
Alexandra H.
29 Mar 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Short family get-away
Alexandra H.
Stayed 5 nights in Mar 2021
Verified
8/10 Good
Jemma L.
29 Dec 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Christmas getaway
Jemma L.
Stayed 3 nights in Dec 2020
Verified
8/10 Good
Julie M.
26 Mar 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Tranquil on the Water
Julie M.
Stayed 3 nights in Mar 2021
Verified
10/10 Excellent
Cheri H.
27 June 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Smooth Sailing!
Cheri H.
Stayed 7 nights in Jun 2023
Verified
10/10 Excellent
Steve D.
29 Aug 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
First time VRBO user very satisfied.
Steve D.
Stayed 7 nights in Aug 2022
Verified
10/10 Excellent
Pamela F.
23 July 2020
Liked: Check-in, communication, location, listing accuracy
Lovely week
Pamela F.
Stayed 7 nights in Jul 2020
Verified
10/10 Excellent
charles b.
23 Apr 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Smooth sailing
charles b.
Stayed 6 nights in Apr 2023
Verified
10/10 Excellent
Anastasia K.
5 Jan 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great getaway!
Anastasia K.
Stayed 7 nights in Dec 2023
Verified
10/10 Excellent
Jessica M.
27 Nov 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect waterfront kids friendly property
Jessica M.
Stayed 3 nights in Nov 2022
Verified
10/10 Excellent
William A.
22 June 2020
Liked: Cleanliness, communication, location, listing accuracy
Disliked: Check-in
Great spot in a nice neighborhood on Chincoteague Island
William A.
Stayed 3 nights in Jun 2020
Verified
10/10 Excellent
Diane J.
11 May 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Weekend Surf Fishing Trip
Diane J.
Stayed 3 nights in May 2023
Verified
10/10 Excellent
Wendy O.
11 Oct 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely home in beautiful part of Chincoteague.
Wendy O.
Stayed 3 nights in Sep 2020
Verified
10/10 Excellent
amanda f.
12 Nov 2021
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect quiet anniversary getaway
amanda f.
Stayed 4 nights in Nov 2021
About the host
Hosted by Seaside Vacations & Sales
Languages:
English
Premier Host
They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback




























