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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

Exterior
Beach
Interior
Property grounds
Property grounds

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms1 bathroomSleeps 6

Popular amenities

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

Explore the area

View 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

Room options

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About the area

Chincoteague

At this holiday home you'll be within a 5-minute walk of Oyster Bay and 2.5 km (1.6 mi) from Maui Jack's Waterpark. Highlights at this holiday home include a kitchen, a washing machine and free WiFi. .Home features a fireplace, a living room and a private garden. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. A Smart TV and a coffee/tea maker are also available. .This smoke-free holiday home offers a water park and barbecues. Plus you'll find laundry facilities. .With a stay at this Deep Hole holiday home, you'll be 2.6 km (1.6 mi) from Captain Timothy Hill House and 2.7 km (1.7 mi) from Chincoteague Channel.

What's nearby

  • Oyster Bay - 12 min walk - 1.1 km
  • Maui Jack's Waterpark - 3 min drive - 2.1 km
  • Captain Timothy Hill House - 3 min drive - 2.8 km
  • Robert N. Reed Downtown Waterfront Park - 3 min drive - 2.9 km
  • Chincoteague National Wildlife Refuge - 5 min drive - 3.4 km

Getting around

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

Restaurants

  • ‪Island Creamery - ‬2 min drive
  • ‪Steamers - ‬2 min drive
  • ‪McDonald's - ‬5 min drive
  • ‪Teaguers - ‬20 min walk
  • ‪Famous Pizza & Sub Shoppe - ‬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

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

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

  • Smoke-free property

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 and check-out are available
Minimum check-in age - 25

Check-out

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

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
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
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 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. On-site 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

Are there any beaches close to Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock?

The closest beach to Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock is Bow Beach (3.2 km).

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

No, this holiday home doesn't have a pool.

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

No, but it has a waterpark and lazy river.

Is there a free airport shuttle available at Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock?

No, Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock does not offer an airport shuttle service.

What time are check-in & check-out at Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock?

Check-in begins at 4:00 PM. Check-out time is 10:00 AM.

Are pets allowed at Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock?

No, pets are not allowed.

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

10/10 Excellent

stephen S.

Liked: Cleanliness

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