Family-Friendly Vacation Rentals in Piney Island, VA: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Family Vacation Rentals
  3.  USA

  4.  Virginia

  5.  Chincoteague
  6.  Piney Island

Refine your search

Price per night

Amenity Filter

Rating

502 Best Family Vacation Rentals in Piney Island (Starting from $168)

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
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
$211
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
Waterfront Living at its finest on Chincoteague Island!
Waterfront Living at its finest on Chincoteague Island!
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

$360
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
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

$555
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
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
$191
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
The Blue Heron- Close to Beach. Shared Community Water Access.
The Blue Heron- Close to Beach. Shared Community Water Access.
House
Chincoteague, VA, 23336, United States
0.3k from Piney Island center

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

4 Bedrooms8 Guests
New to Booking
$327
Average price / night
Check Availability
Hailey's Roundhouse - New & Unique Home w/Water Access!
Hailey's Roundhouse - New & Unique Home w/Water Access!
House
Deep Hole, VA, USA
0.3k from Piney Island center

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

3 Bedrooms9 Guests
New to Booking
$374
Average price / night
Check Availability
SANDPIPER HOUSE: A Modern Mid-Century Retreat on Piney Island
SANDPIPER HOUSE: A Modern Mid-Century Retreat on Piney Island
House
Chincoteague Island, VA, 23336, United States
0.4k from Piney Island center

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

3 Bedrooms8 Guests
9.4

Superb

70 reviews

$258
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
Aramabad- Close to Beach. Shared Water Access.
Aramabad- Close to Beach. Shared Water Access.
House
Chincoteague, VA, 23336, United States
0.4k from Piney Island center

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

4 Bedrooms8 Guests
9.0

Fabulous

7 reviews

$215
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
Happy Hideaway on Chincoteague - Closest community to the Beach!
Happy Hideaway on Chincoteague - Closest community to the Beach!
House
Chincoteague Island, VA, 23336, United States
0.4k from Piney Island center

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

3 Bedrooms8 Guests
9.8

Exceptional

21 reviews

$228
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
Blue Heron-Closest Neighborhood to the Beach.
Blue Heron-Closest Neighborhood to the Beach.
House
Chincoteague, VA, 23336, United States
0.5k from Piney Island center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$207
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
Cedarfield- Close to Beach. Shared Community Water Access.
Cedarfield- Close to Beach. Shared Community Water Access.
House
Chincoteague, VA, 23336, United States
0.5k from Piney Island center

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

2 Bedrooms6 Guests
New to Booking
$169
Average price / night
Check Availability
Treehouse- Fire Pit, Basketball Court, Bikes, Kayaks & Casita w/ Game Room
Treehouse- Fire Pit, Basketball Court, Bikes, Kayaks & Casita w/ Game Room
House
Chincoteague, VA, 23336, United States
0.5k from Piney Island center

AC, Arcade, Balcony, Barbecue, Dryer, Elevator, Fireplace, Free Parking, Heater

5 Bedrooms15 Guests
New to Booking
$701
Average price / night
Check Availability
Willet's Way- Close to Beach w/ Assateague Views & Boat Dock
Willet's Way- Close to Beach w/ Assateague Views & Boat Dock
House
Chincoteague, VA, 23336, United States
0.6k from Piney Island center

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

2 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$290
Average price / night
Check Availability
Happy Ours | Pet-Friendly Chincoteague Home w/ Fenced Yard, Firepit & Bikes
Happy Ours | Pet-Friendly Chincoteague Home w/ Fenced Yard, Firepit & Bikes
House
Chincoteague, VA, 23336, United States
0.7k from Piney Island center

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

3 Bedrooms6 Guests
New to Booking
$217
Average price / night
Check Availability
Driftwood-Fire Pit, Bikes, Close to Beach
Driftwood-Fire Pit, Bikes, Close to Beach
House
Chincoteague, VA, 23336, United States
0.7k from Piney Island center

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

3 Bedrooms6 Guests
New to Booking
$220
Average price / night
Check Availability
Pony Dreams | New Island Home, Fully Stocked Kitchen, Crab Shack Gazebo, Boat Parking
Pony Dreams | New Island Home, Fully Stocked Kitchen, Crab Shack Gazebo, Boat Parking
House
Chincoteague Island, VA, 23336, United States
1.0k from Piney Island center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

3 Bedrooms8 Guests
New to Booking
$350
Average price / night
Check Availability
Eureka! on Deep Hole Creek - Waterfront!  Sleeps 16
Eureka! on Deep Hole Creek - Waterfront! Sleeps 16
House
Chincoteague, VA, 23336, United States
1.0k from Piney Island center

AC, Balcony, Barbecue, Dryer, Elevator, Extra Bed, Fireplace, Free Parking, Heater

8 Bedrooms16 Guests
9.8

Exceptional

29 reviews

$1993
Average price / night
Check Availability
Brittany-Private Deep Water Pier & Boat Dock
Brittany-Private Deep Water Pier & Boat Dock
House
Chincoteague, VA, 23336, United States
1.0k from Piney Island center

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

4 Bedrooms12 Guests
New to Booking
$830
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals 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 Family Vacation Rentals in Piney Island.

Stay Near Piney Island's Top Attractions

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

Piney Island Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 502 verified family-friendly vacation rentals in Piney Island. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Piney Island vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $168 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Piney Island offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Piney Island are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Piney Island often include amenities such as Child Friendly, Fireplace/Heating, and Internet. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.