Piney Island Vacations from $212
Book a Hotel + Flight or Car together to unlock savings
Your Piney Island Vacation
With a customized vacation package to Piney Island, you can spend less time planning and more time uncovering this fascinating neighborhood. From its nature to its views, there's so much to discover here. Begin your trip to Piney Island by heading to nearby attractions such as Maui Jacks Waterpark, Robert N. Reed Downtown Waterfront Park and Oyster Bay. Expedia will help you turn your ideal Piney Island vacation into reality, no matter your travel plans or budget.
The Latest Piney Island Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Ocean Sands Beach Boutique Inn - Stay At the Beach
Price was $306, price is now $212 per person
$212
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
7.4/10 Good! (1,001 reviews)
We booked 2 bed and a sofa and was comfortable for 5. the room was spacious. close to many restaurants. Tele check in was easy. Popcorn flavors were awesome.
One of the biggest negative, they don't have proper Breakfast. they gave granola bar, apple sauce, cereal. If this were the options I wouldn't have definitely selected this hotel for stay. One of the major thing we look for during vacation is a nice family breakfast. It was totally ruined. They better don't advertise themselves as giving breakfast.
Reviewed on Sep 1, 2025
John Yancey Oceanfront Inn
Save 100% on your flight
Price was $590, price is now $380 per person
$380
per person
Oct 16 - Oct 19
just found
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9/10 Wonderful! (1,740 reviews)
The staff, mainly, Bud, was very friendly. I totally would come back!
Reviewed on Sep 1, 2025
Sea Ranch Resort
Save 100% on your flight
Price was $610, price is now $397 per person
$397
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,010 reviews)
This place is definitely not a resort! The room had bare minimum amenities. The door to the balcony didn’t lock; the bathroom had a funny smell to it; and there is NO maid service! No one came in to make the bed, empty the trash, vacuum the carpet, or replace the towels! For the high price I paid to stay there, it was subpar in my opinion.
The bistro and bar were convenient and nice.
Overall, it was disappointing in general. I would not go back.
Reviewed on Sep 1, 2025
Hilton Norfolk The Main
Downtown Norfolk
Save 100% on your flight
Price was $1,500, price is now $1,057 per person
$1,057
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9/10 Wonderful! (1,001 reviews)
Everything about it was good
Reviewed on Aug 10, 2025
Piney Island Hotel Deals
Days Inn by Wyndham Chincoteague Island
7020 Maddox Blvd, Chincoteague, VA
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $84 total per night from Oct 2 to Oct 3
$84 total
Oct 2 - Oct 3
Total with taxes and fees
Spark by Hilton Chincoteague Island
7105 Maddox Boulevard, Chincoteague, VA
$125 nightly
The price is $141 total per night from Sep 22 to Sep 23
$141 total
Sep 22 - Sep 23
Total with taxes and fees
Refuge Inn
7058 Maddox Blvd., Chincoteague, VA
$145 nightly
The price is $163 total per night from Sep 7 to Sep 8
$163 total
Sep 7 - Sep 8
Total with taxes and fees
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Piney Island
Maui Jack's Waterpark
Bring your family to Maui Jack's Waterpark and enjoy this exciting theme park in Chincoteague.
Museum of Chincoteague
You can spend an afternoon exploring the galleries in Museum of Chincoteague during your trip to Chincoteague. While you're in the area, stroll along the beautiful beaches.
Things to do
Grand Boat Tour around Chincoteague and Assateague Islands
$89
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.