Owner Direct Vacation Rentals in Piney Island

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. ODVR
  2. Vacation Rentals
  3.  USA

  4.  Virginia

  5.  Chincoteague
  6.  Piney Island

Refine your search

Price per night

Amenity Filter

Rating

913 Piney Island Vacation Homes From $168

Looking for the ideal vacation rental in Piney Island? Discover an extensive gallery of private rentals offering space, comfort, and authentic local character. Owner Direct simplifies your search by matching you with verified property options.

Island Sunrise - Pet friendly, waterfront duplex!
Island Sunrise - Pet friendly, waterfront duplex!
House
Deep Hole, VA, USA
0.1k from Piney Island center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$522
Average price / night
Check Availability
Hailey's Roundhouse - New & Unique Home w/ Water Access!
Hailey's Roundhouse - New & Unique Home w/ Water Access!
House
Chincoteague Island, VA, 23336, United States
0.1k from Piney Island center

AC, Dryer, Extra Bed, Heater, Internet, Kitchen, Laundry, Living Area, Microwave

3 Bedrooms9 Guests
9.2

Superb

5 reviews

$440
Average price / night
Check Availability
Channel Watch - Waterfront home with private Pier!
Channel Watch - Waterfront home with private Pier!
House
Deep Hole, VA, USA
0.2k from Piney Island center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms7 Guests
8.0

Good

1 reviews

$168
Average price / night
Check Availability
Ohana Sunrise - VERY NICE 3BR, Close to the beach - Linens & Towels provided
Ohana Sunrise - VERY NICE 3BR, Close to the beach - Linens & Towels provided
House
Chincoteague, VA, 23336, United States
0.1k from Piney Island center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
8.8

Fabulous

5 reviews

$290
Average price / night
Check Availability
Southern Exposure - Waterfront with boat dock!
Southern Exposure - Waterfront with boat dock!
House
Deep Hole, VA, USA
0.2k from Piney Island center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms7 Guests
New to Booking
$529
Average price / night
Check Availability
Hummingbird Haven- 3BR Home | Close to Beach
Hummingbird Haven- 3BR Home | Close to Beach
House
Chincoteague Island, VA, 23336, United States
0.1k from Piney Island center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area

3 Bedrooms6 Guests
New to Booking
$318
Average price / night
Check Availability
Chincoteague
Chincoteague
House
Chincoteague, VA, USA
0.2k from Piney Island center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$292
Average price / night
Check Availability
Gorgeous duplex with dock by Seaside Vacations & Sales
Gorgeous duplex with dock by Seaside Vacations & Sales
House
Chincoteague, VA, 23336, United States
0.1k from Piney Island center

AC, Balcony, Barbecue, Dryer, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
9.0

Fabulous

34 reviews

$288
Average price / night
Check Availability
The Happy Crab
The Happy Crab
House
Deep Hole, VA, USA
0.2k from Piney Island center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

1 Bedroom6 Guests
New to Booking
$381
Average price / night
Check Availability
Channel Watch | Assateague Channel Waterfront w/ Private Dock, Screened Porch, Balconies & Sunrises
Channel Watch | Assateague Channel Waterfront w/ Private Dock, Screened Porch, Balconies & Sunrises
House
Chincoteague Island, VA, 23336, United States
0.1k from Piney Island center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
New to Booking
$472
Average price / night
Check Availability
Island Sunrise | Waterfront w/ Deep Water Dock, Assateague Views, 3 Decks + Pet Friendly
Island Sunrise | Waterfront w/ Deep Water Dock, Assateague Views, 3 Decks + Pet Friendly
House
Chincoteague Island, VA, 23336, United States
0.1k from Piney Island center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
9.4

Superb

3 reviews

$482
Average price / night
Check Availability
Cedar Haven
Cedar Haven
House
Deep Hole, VA, USA
0.4k from Piney Island center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

1 Bedroom6 Guests
New to Booking
$399
Average price / night
Check Availability
Silver Thatch -4BR home Close to the beach. Linens and Towels Provided.
Silver Thatch -4BR home Close to the beach. Linens and Towels Provided.
House
Chincoteague, VA, 23336, United States
0.2k from Piney Island center

AC, Dryer, Free Parking, Heater, Kitchen, Laundry, Microwave, No Smoking, TV

4 Bedrooms8 Guests
8.0

Good

7 reviews

$300
Average price / night
Check Availability
Shackeau East
Shackeau East
House
Deep Hole, VA, USA
0.4k from Piney Island center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

1 Bedroom4 Guests
New to Booking
$213
Average price / night
Check Availability
The Happy Crab by Seaside Vacations & Sales
The Happy Crab by Seaside Vacations & Sales
House
Chincoteague Island, VA, 23336, United States
0.2k from Piney Island center

AC, Balcony, Barbecue, Dryer, Heater, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
9.0

Fabulous

17 reviews

$257
Average price / night
Check Availability
Slack Tide
Slack Tide
House
Deep Hole, VA, USA
0.4k from Piney Island center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Family

1 Bedroom8 Guests
New to Booking
$325
Average price / night
Check Availability
Mermaid Manor- 4BR Waterfront | Private Pier | Close to Beach
Mermaid Manor- 4BR Waterfront | Private Pier | Close to Beach
House
Chincoteague, VA, 23336, United States
0.3k from Piney Island center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$740
Average price / night
Check Availability
Teague Time
Teague Time
House
Chincoteague, VA, USA
0.4k from Piney Island center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay, Family

1 Bedroom6 Guests
New to Booking
$331
Average price / night
Check Availability
 Featured DC magazine 10 BEST/Waterview CLOSEST community to BEACH 3 decks.
Featured DC magazine 10 BEST/Waterview CLOSEST community to BEACH 3 decks.
House
Chincoteague Island, VA, 23336, United States
0.3k from Piney Island center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

158 reviews

$275
Average price / night
Check Availability
Avocet- Shared Community Water Access, Close to Beach.
Avocet- Shared Community Water Access, Close to Beach.
House
Chincoteague, VA, 23336, United States
0.3k from Piney Island center

AC, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms10 Guests
New to Booking
$325
Average price / night
Check Availability
Acorn - Nice home in great location. Big porch. -LINENS AND TOWELS PROVIDED
Acorn - Nice home in great location. Big porch. -LINENS AND TOWELS PROVIDED
House
Chincoteague, VA, 23336, United States
0.3k from Piney Island center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
9.8

Exceptional

11 reviews

$301
Average price / night
Check Availability

Pro Tip:
OwnerDirectVacationRental aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Piney Island.

Stay Near Piney Island's Top Attractions

OwnerDirectVacationRental can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.

Piney Island Vacation Rentals on the Map

Why Travelers Love Using Owner Direct to
Find Austin Vacation Rentals

What makes our vacation rentals stand out?

check-mark

Verified Properties

Every vacation rentals shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.

check-mark

Value You Can Trust

Compare a range of properties and find fair, transparent pricing—no hidden fees.

check-mark

Endless Variety

From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.

Frequently Asked Questions

There are a lot of options in Piney Island. If you plan on staying in the Piney Island area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals in Piney Island

You can explore 913 verified vacation rentals in Piney Island. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Piney Island vary depending on the season, property size, and location. Rates typically start from around $168 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Piney Island include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Piney Island welcome pets. Currently, 15 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it's recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Piney Island often include amenities such as Fireplace/Heating, Internet, and Sports/Activities. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.