Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock | House in Chincoteague
2 Bedroom House in Deep Hole, Chincoteague
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.
Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock is located in Deep Hole. Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock provides accommodation, featuring Parking, View, Sports/Activities, among other amenities. This House features Parking, View, Sports/Activities, to make your stay a comfortable one.
Island Generations | 2BR Coastal Retreat on Little Oyster Bay with Private Dock has 2 Bedrooms , 1 Bathroom, and max occupancy of 6 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Deep Hole has interesting places to visit. If you want to learn more about the House in Deep Hole, such as places to visit and things to do nearby, you can check below to learn more.
This Property is OneKey Eligible
Earn OneKeyCash for every dollar spent on eligible vacation rentals, villas, cottages, cabins, and more when you book on Vrbo.
Amenities
Facility Overview
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Air conditioning
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Heating
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1 bathroom
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2 bedrooms
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Living room
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Fireplace
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Microwave
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Stovetop
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Refrigerator
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Coffee/tea maker
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Cookware/dishes/utensils
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Oven
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Toaster
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Laundry facilities
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Washing machine and dryer
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Onsite parking
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No pets allowed
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Smoke-free property
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Surfing/body boarding nearby
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Power boating nearby
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Jet skiing nearby
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Tennis on site
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Ecotours nearby
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Water park
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Wildlife and game walks nearby
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Birdwatching nearby
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Swimming nearby
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Golf nearby
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Sailing nearby
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Smart TV with cable/satellite service
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English
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Playground
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Free WiFi
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Yard
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Dock
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Porch or lanai
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Firepit
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Barbecue grill
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Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)
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Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
Policies
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 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 onsite parties or group events are strictly prohibited special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed 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
Reviews
FAQ's
Is this Deep Hole house pet-friendly for guests?
No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.
Does the Deep Hole house have a swimming pool?
No, this Deep Hole house does not have a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.
How much does it cost per night to stay in Deep Hole house?
Best-rates for the Deep Hole house starts from $244 per night with includes Parking, View, Sports/Activities, Fireplace/Heating, Barbecue/Outdoor Cooking, Child Friendly, Internet, Kitchen, Air Conditioner, TV, Balcony/Terrace, Security/Safety, Laundry with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.
Is Deep Hole house a family-friendly place to stay?
Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.
Is the Deep Hole house wheelchair accessible or offer services for disabled guests?
Based on the information received from our partner, the Deep Hole house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.
What is the minimum night stay policy for the Deep Hole house?
Based on the information reported by the owner or manager, the Deep Hole house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.
What cancellation policy is in place for Deep Hole house?
Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.
