Deep Hole
Chincoteague
Visit Deep Hole
Things to do
Chincoteague and Assateague Island Boat Tour with Capt. John
S$121
per adult
Chincoteague/Assateague Kayak, Canoe, Paddle Board Rentals
S$88
per adult
Chincoteague: Guided Sunset Kayak Tour with Wildlife Views
S$96
per adult
Top hotels in Deep Hole
Waterside Inn
3761 Main St Chincoteague VA
The price is S$82 per night from 20 Oct to 21 Oct
S$82
per night
20 Oct - 21 Oct
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 S$114 per night from 18 Oct to 19 Oct
S$114
per night
18 Oct - 19 Oct
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 S$278 per night from 15 Oct to 16 Oct
S$278
per night
15 Oct - 16 Oct
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! (658 reviews)
"Everything about the amenities was great. Nicely laid out. Beautiful landscaping and overnight lighting. Prime location. Nice private small sandy beach area and pool. Bikes available for use free. Luggage carts were helpful."
Reviewed on 12 Oct, 2026
Comfort Suites Chincoteague Island Bayfront Resort
4195 Main St Chincoteague VA
The price is S$166 per night from 11 Nov to 12 Nov
S$166
per night
11 Nov - 12 Nov
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! (1,000 reviews)
"The location of this hotel was convenient to walking to stores and restaurants. It was nicely landscaped with a fountain, and had comfortable seating outside for viewing the bay. It also offered a heated outdoor pool which I enjoyed for swimming, as well as an indoor pool and hot tub. The staff was ..."
Reviewed on 13 Oct, 2026
Best Western Plus Pocomoke City
125 Newtowne Blvd Pocomoke City MD
The price is S$163 per night from 1 Nov to 2 Nov
S$163
per night
1 Nov - 2 Nov
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! (1,005 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.
