Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)
Airport, Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)
67 min drive
Rooms & beds
2 bedrooms (sleeps 6)
1 bathroom
Hall Bathroom
Spaces
Porch or lanai
Kitchen
Outdoor play area
Dining area
About this property
Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock
Experience classic Chincoteague Island charm with all the modern comforts at this lovingly updated waterfront home. Situated by Little Oyster Bay, the property features a private bulkhead boat dock perfect for crabbing, kayaking, boating, or simply enjoying peaceful waterfront moments.
Inside, the home blends coastal charm with modern updates. A comfortable living room opens to the dining area, and classic kitchen creating a warm and inviting space for meals and gatherings. Two bedrooms, each with a queen bed, share a full hallway bathroom, making the home perfect for couples, small families, or friends traveling together.
Relaxation is easy at this home. The enclosed four-season porch offers a cozy spot to enjoy bay views in any weather, while the outdoor space features shade trees, a porch swing, and a covered grill area. From the yard, a short lane leads directly to the private dock, where you can launch a kayak, fish, or simply take in the serene bay setting. Keep an eye out for neighboring horses grazing nearby, adding a true Chincoteague Island experience.
Outdoor & Waterfront Amenities
Private bulkhead boat dock for kayaking, crabbing, or boating
Enclosed four-season porch with waterfront views
Covered grill area for outdoor dining
Yard with shade trees and porch swing
Short lane to the dock for easy water access
Opportunity to spot Chincoteague’s famous horses
Prime Chincoteague Location
This home offers a quiet waterfront retreat while remaining close to Chincoteague Island’s restaurants, shops, and attractions. A short drive brings you to Assateague Island for beaches, wildlife, and the famous wild ponies.
Why Guests Love This Home
Classic Chincoteague charm with modern updates
Private dock on Little Oyster Bay for boating and crabbing
Relaxing four-season porch with scenic water views
Yard, grill area, and porch swing for outdoor enjoyment
Unique opportunity to see horses from the property
Your Chincoteague Escape
Whether you are kayaking, crabbing, grilling outdoors, or relaxing on the four-season porch, this home offers everything needed for a memorable Chincoteague Island waterfront vacation.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space
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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 not indicated whether 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
Deep Hole, a neighbourhood in Chincoteague, is home to this holiday home. Chincoteague National Wildlife Refuge and Oyster Bay reflect the area's natural beauty and area attractions include Maui Jack's Waterpark and Wallops Flight Facility. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Robert N. Reed Downtown Waterfront Park - 3 min drive - 2.9 km
Chincoteague National Wildlife Refuge - 5 min drive - 3.4 km
Assateague Lighthouse - 7 min drive - 5.1 km
Getting around
Ocean City, MD (OCE-Ocean City Municipal) - 67 min drive
Restaurants
Island Creamery - 2 min drive
McDonald's - 5 min drive
Steamers - 2 min drive
Famous Pizza & Sub Shoppe - 4 min drive
Teaguers - 20 min walk
Frequently asked questions
Is Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock?
As of 26 Mar, 2026, prices found for a 1-night stay for 2 adults at Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock on 25 May, 2026 start from S$200, 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 Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock?
On-site parking is available at the property.
What time is check-in at Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock?
Check-in begins at 4:00 PM.
What time is check-out at Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock?
Checkout is at 10:00 AM.
Where is Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock located?
Located in Deep Hole, this holiday home is within 2 miles (3 km) of Oyster Bay, Maui Jack's Waterpark and Captain Timothy Hill House. Chincoteague Channel and Robert N. Reed Downtown Waterfront Park are also within 2 miles (3 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Sewer issues flooded sun room everytime you did laundry but got through it and did not let it ruin a weeks vacation great spot booked again next year same week
stephen S.
Stayed 7 nights in Sep 2024
About the host
Hosted by Island Getaways, LLC
Languages:
English
Premier Host
They consistently provide great experiences for their guests