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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

A white house with a chimney, a wooden porch, and a fenced yard. - Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock (Chincoteague)
A wooden dock extending into calm water with a sandy area in the foreground and a flat landscape in the background. - Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock (Chincoteague)
Two white Adirondack chairs by a wooden dock overlooking a body of water. - Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock (Chincoteague)
A rural setting with a dirt path leading to a white house with a gabled roof and a covered porch. - Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock (Chincoteague)
A cozy room with wooden walls, a large window, a dining table with chairs, and two wicker sofas with cushions. - Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock (Chincoteague)
At Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock, you can look forward to a water park, a firepit, and a playground. Stay connected with free in-room WiFi, and guests can find other amenities such as laundry facilities.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space

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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.

    Maximum 2 pets allowed - Additional pet fee required per pet

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About the neighborhood

Deep Hole, a neighborhood in Chincoteague, is home to this vacation 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 hiking and ecotours nearby. Visit our Chincoteague travel guide
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Map
Chincoteague, VA

What's nearby

  • A rustic wooden structure with a rusted roof by a body of water.
    Oyster Bay
    14 min walk - 1.2 km
  • A lake with a dock extending into it, surrounded by houses and greenery.
    Chincoteague Channel
    3 min drive - 2.8 km
  • A tall lighthouse with alternating red and white stripes, surrounded by dense forest and leafless trees.
    Chincoteague National Wildlife Refuge
    6 min drive - 4.8 km
  • A red and white lighthouse with a small adjacent building, surrounded by trees and a clear sky.
    Assateague Lighthouse
    8 min drive - 6.2 km
  • Maui Jack's Waterpark
    4 min drive - 3.1 km

Getting around

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

Restaurants

  • Island Creamery
    2 min drive
  • McDonald's
    5 min drive
  • Ropewalk
    4 min drive
  • Captain Zack's Seafood
    20 min walk
  • Asian Express
    4 min drive

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 is parking?

Onsite 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?

Check-out 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 vacation home is within 2 mi (3 km) of Oyster Bay, Chincoteague Channel, and Maui Jack's Waterpark. Captain Timothy Hill House and Robert N. Reed Downtown Waterfront Park are also within 2 mi (3 km).

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Reviews

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

10

Exceptional

8.0

Cleanliness

10

Location
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

Reviews

Verified review

10/10 Excellent

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