Deep Hole
Chincoteague
Visit Deep Hole
Things to do
Chincoteague's Up The Bay Pony and Wildlife Tour by Boat
P4,939
per adult
94% of travellers recommend
Chincoteague: Guided Sunset Kayak Tour with Wildlife Views
P4,689
per adult
Chincoteague and Assateague Island Boat Tour with Capt. John
P5,928
per adult
Chincoteague: Premier Pony & Wildlife Small Group Boat Tour
P4,939
per adult
100% of travellers recommend
Chincoteague & Assateague Small-Group Sunset Boat Tour
P5,564
per adult
Top hotels in Deep Hole
Waterside Inn
3761 Main St Chincoteague VA
The price is P3,843 per night from Oct 19 to Oct 20
P3,843
per night
Oct 19 - Oct 20
Stay at this hotel in Chincoteague. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular ...
Chincoteague Inn
4417 Deep Hole Road Chincoteague VA
The price is P4,958 per night from Oct 27 to Oct 28
P4,958
per night
Oct 27 - Oct 28
Stay at this motel in Chincoteague. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our 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 Oct 12, 2026
Key West Cottages
4251 Main Street Chincoteague VA
The price is P12,157 per night from Oct 15 to Oct 16
P12,157
per night
Oct 15 - Oct 16
Stay at this cottage in Chincoteague. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular ...
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 Oct 12, 2026
Comfort Suites Chincoteague Island Bayfront Resort
4195 Main St Chincoteague VA
The price is P7,177 per night from Nov 11 to Nov 12
P7,177
per night
Nov 11 - Nov 12
Stay at this hotel in Chincoteague. Enjoy free breakfast, free parking, and a 24-hour fitness center. 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 Oct 13, 2026
Best Western Plus Pocomoke City
125 Newtowne Blvd Pocomoke City MD
The price is P7,129 per night from Nov 1 to Nov 2
P7,129
per night
Nov 1 - Nov 2
Book a stay at this business-friendly hotel in Pocomoke City. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,005 reviews)
"Staff very friendly and helpful. Breakfast was yummy"
Reviewed on Oct 14, 2026
Blufin Bungalows & Marina
2477 Main St Chincoteague VA
Stay at this vacation home in Chincoteague. Enjoy free WiFi, 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 and neighborhoods 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
While there might not be top attractions in Snotty Ridge, you can explore the larger area and discover places like Robert N. Reed Downtown Waterfront Park and Assateague Point.
Down the Marsh
If you're looking for some top things to see and do in Down the Marsh and surrounding area, you can visit Robert N. Reed Downtown Waterfront Park and Assateague Point.
Birch Town
While Birch Town isn't home to many top sights, Maui Jack's Waterpark and Museum of Chincoteague are some notable places to visit nearby.
