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

Vacation home perfectly located for exploring Deep Hole

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

Exterior
Smart TV, fireplace
Dining
Property grounds
Fridge, microwave, oven, stovetop

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms1 bathroomSleeps 6

Popular amenities

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

Explore the area

View in a 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

Room options

About the neighborhood

Chincoteague

Deep Hole stay.With a stay at this Deep Hole vacation home, you'll be within half a mile (1 km) of Oyster Bay and 2 miles (3 km) of Maui Jack's Waterpark. Captain Timothy Hill House and Chincoteague Channel are also within 2 miles (3 km).
View more Vacation Homes in ChincoteagueOpens in a new window

What's nearby

  • Oyster Bay - 14 min walk - 0.8 miles
  • Robert N. Reed Downtown Waterfront Park - 3 min drive - 2.2 miles
  • Maui Jack's Waterpark - 4 min drive - 2.0 miles
  • Captain Timothy Hill House - 4 min drive - 2.2 miles
  • Chincoteague National Wildlife Refuge - 5 min drive - 2.8 miles

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
  • ‪Teaguers - ‬20 min walk
  • ‪Ropewalk - ‬4 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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.

Similar properties

Exterior
Comfort Suites Chincoteague Island Bayfront Resort
Downtown Chincoteague
  • Pool
  • Hot tub
  • Breakfast included
  • Parking included
4.8 out of 5, Exceptional, 1,007 reviews
$237 nightly
The price is $267
Jun 8 - Jun 9
Total with taxes and fees
Comfort Suites Chincoteague Island Bayfront Resort

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Bedrooms

  • 2 bedrooms

Bathroom

  • 1 bathroom

Living spaces

  • Fireplace
  • Living room

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Dock
  • Firepit
  • Porch/lanai
  • Yard

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Things to do

  • Tennis
  • Water park
  • Basketball nearby
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Hunting nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM
Contactless check-out available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events 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
Onsite 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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited.

Property is also known as

House Chincoteague
7027
House Private vacation home
House Private vacation home Chincoteague

Frequently asked questions

How close is Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock to the airport?

This vacation home is 56.2 mi (67-min drive) away from the Ocean City, MD (OCE-Ocean City Municipal) airport, the closest popular airport to the property.

Does Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock to the beach?

This vacation home is 6.4 mi (23-min drive) from Bow Beach.

Does Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock?

No, there is no casino at this vacation home.

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.

Is there free parking at Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock?

Free parking is not available at this vacation home.

Does Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock have a pool?

This vacation home does not have a pool.

Does Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock have a spa?

There are no spa services available at this vacation home.

How close is Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock to downtown Chincoteague?

This vacation home is 1.6 mi away from Chincoteague.

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

Reviews

10

Exceptional

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

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