Deep Hole Travel Guide
Chincoteague
Visit Deep Hole
Things to do
Chincoteague/Assateague Kayak, Canoe, Paddle Board Rentals
฿2,304
per adult
Chincoteague: Guided Sunset Kayak Tour with Wildlife Views
฿2,504
per adult
Chincoteague & Assateague Small-Group Sunset Boat Tour
฿2,971
per adult
Chincoteague's Up The Bay Pony and Wildlife Tour by Boat
฿2,638
per adult
94% of travellers recommend
Chincoteague's and Assateague’s Grand Boat Tour with Capt.John
฿2,971
per adult
100% of travellers recommend
Chincoteague's Kayak Tour around the Islands
฿2,971
per adult
Top hotels in Deep Hole
Waterside Inn
3761 Main St Chincoteague VA
The price is ฿2,058 per night from 20 Oct to 21 Oct
฿2,058
฿2,312 total
20 Oct - 21 Oct
includes taxes & fees
Stay at this hotel in Chincoteague. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the pool and the helpful staff in their reviews. Popular ...
Chincoteague Inn
4417 Deep Hole Road Chincoteague VA
The price is ฿2,657 per night from 18 Oct to 19 Oct
฿2,657
฿2,984 total
18 Oct - 19 Oct
includes taxes & fees
Stay at this motel in Chincoteague. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8.6/10 Excellent! (1,000 reviews)
"The room was semi clean and in a good spot but the bed linens were strange. The comforter felt like wax paper. The floors turned my socks black but the bathroom was clean. Our tub backed up with what smelled like sewage but they moved us right away. No carts to move all our luggage and food which ..."
Reviewed on 12 Oct 2026
Key West Cottages
4251 Main Street Chincoteague VA
The price is ฿6,784 per night from 18 Oct to 19 Oct
฿6,784
฿7,618 total
18 Oct - 19 Oct
includes taxes & fees
Stay at this cottage in Chincoteague. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the pool and the helpful staff in their reviews. ...
9.8/10 Exceptional! (660 reviews)
"We love Key West, but we don’t want to fly or drive there anymore. Key West Cottages made us feel like we were in Key West. The cottage was beautiful and they’re all so colorful! I loved the crushed shell pathways. The wagons they provide for moving your things to the cottage are a great idea. We ..."
Reviewed on 15 Oct 2026
Comfort Suites Chincoteague Island Bayfront Resort
4195 Main St Chincoteague VA
The price is ฿3,622 per night from 5 Nov to 6 Nov
฿3,622
฿4,103 total
5 Nov - 6 Nov
includes taxes & fees
Stay at this hotel in Chincoteague. Enjoy free breakfast, free parking and a 24-hour fitness centre. Our guests praise the breakfast and the helpful staff in ...
9.6/10 Exceptional! (1,001 reviews)
"Strong marijuana smell in a property advertised as smoke-free. The hotel clearly says it is a smoke-free property, which is a big reason I booked it. We were given a connecting room, and the guests next door were smoking marijuana. The smell came straight into our room and was strong and obvious. ..."
Reviewed on 15 Oct 2026
Best Western Plus Pocomoke City
125 Newtowne Blvd Pocomoke City MD
The price is ฿3,818 per night from 1 Nov to 2 Nov
฿3,818
฿4,276 total
1 Nov - 2 Nov
includes taxes & fees
Stay at this business-friendly hotel in Pocomoke City. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (1,000 reviews)
"Staff very friendly and helpful. Breakfast was yummy"
Reviewed on 14 Oct 2026
Blufin Bungalows & Marina
2477 Main St Chincoteague VA
Stay at this holiday home in Chincoteague. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Chincoteague Channel and Assateague Point ...
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.
Where to stay in Deep Hole
Find the best Deep Hole areas for the activities you enjoy most.
Photo by Michael Gibson
Open Photo by Michael Gibson
Downtown Chincoteague
While visiting Downtown Chincoteague, you might make a stop by sights like Robert N. Reed Downtown Waterfront Park and Chincoteague Channel.
Piney Island
While visiting Piney Island, you might make a stop by sights like Maui Jack's Waterpark and Museum of Chincoteague.
Snotty Ridge
Snotty Ridge might not have many top sights, but Robert N. Reed Downtown Waterfront Park and Assateague Point are two attractions nearby that you can check out.
Down the Marsh
While there might not be top attractions in Down the Marsh, you can explore the larger area and discover places like Robert N. Reed Downtown Waterfront Park and Assateague Point.
Birch Town
Though Birch Town may not have many top sights, you can venture to the surrounding area to see attractions like Maui Jack's Waterpark and Museum of Chincoteague.
