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
Private bulkhead boat dock located on Little Oyster Bay
Private bulkhead boat dock located on Little Oyster Bay
private bulkhead boat dock located on Little Oyster Bay
Living Room with Queen Sleep Sofa

Reviews

10 out of 10
Exceptional
2 bedrooms1 bathroomSleeps 6

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

Explore the area

View in a map
Chincoteague, VA
  • Place, Oyster Bay
    ‪12 min walk‬
  • Place, Ocean City Boardwalk
  • Place, Maui Jack's Waterpark
    ‪3 min drive‬
  • 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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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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 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.
Map
Chincoteague, VA

What's nearby

  • Oyster Bay - 12 min walk - 1.1 km
  • Maui Jack's Waterpark - 3 min drive - 2.1 km
  • 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.
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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

About the host

Hosted by Island Getaways, LLC

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