Entire home

Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock

Photo gallery for Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock

Unique location at the end of Deephole Road
Little Oyster Bay
Living Room with Queen Sleep Sofa
Enclosed 4-season porch.
Private bulkhead boat dock located on Little Oyster Bay

Reviews

10 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 6

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue
  • Dock

Explore the area

View map
Chincoteague, VA
  • Place, Oyster Bay
    ‪14 min walk‬
  • Place, Maui Jack's Waterpark
    ‪4 min drive‬
  • Place, Chincoteague National Wildlife Refuge
    ‪5 min drive‬
  • Airport, Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)
    ‪71 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.

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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. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with ecotours and cycling nearby.
Map
Chincoteague, VA

What's nearby

  • Oyster Bay - 14 min walk - 1.2 km
  • Robert N. Reed Downtown Waterfront Park - 3 min drive - 3.5 km
  • Maui Jack's Waterpark - 4 min drive - 3.1 km
  • Chincoteague National Wildlife Refuge - 5 min drive - 4.5 km
  • University of Maryland Eastern Shore - 55 min drive - 69.5 km

Getting around

  • Ocean City, MD (OCE-Ocean City Municipal) - 67 min drive

Restaurants

  • ‪McDonald's - ‬5 min drive
  • ‪Steamers - ‬2 min drive
  • ‪Island Creamery - ‬2 min drive
  • ‪Teaguers - ‬20 min walk
  • ‪Ropewalk - ‬4 min drive

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 1 out of 1 reviews
Rating 8 - Good. 0 out of 1 reviews
Rating 6 - Okay. 0 out of 1 reviews
Rating 4 - Poor. 0 out of 1 reviews
Rating 2 - Terrible. 0 out of 1 reviews

8.0/10

Cleanliness

10/10

Check-in

8.0/10

Communication

10/10

Location

8.0/10

Listing accuracy

Reviews

Verified

10/10 Excellent

stephen S.

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

Had sewer issues but still made most of it

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
Stayed 7 nights in Sep 2024
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