Deep Hole Travel Guide
Chincoteague
Visit Deep Hole
Things to do
Chincoteague/Assateague Kayak, Canoe, Paddle Board Rentals
฿2,283
per adult
Chincoteague & Assateague Small-Group Sunset Boat Tour
฿2,945
per adult
Chincoteague's Up The Bay Pony and Wildlife Tour by Boat
฿2,618
per adult
94% of travellers recommend
Guided Kayak Tour to see ponies, birds, dolphins and more
฿2,485
per adult
100% of travellers recommend
Chincoteague's and Assateague’s Grand Boat Tour with Capt.John
฿2,945
per adult
100% of travellers recommend
Chincoteague's Kayak Tour around the Islands
฿2,945
per adult
Top hotels in Deep Hole
Chincoteague Inn
4417 Deep Hole Road Chincoteague VA
The price is ฿3,254 per night from 27 Sept to 28 Sept
฿3,254
per night
27 Sept - 28 Sept
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! (1,003 reviews)
"Clean and extremely nice rooms for a motel, very clean pool as well. I felt very safe staying here. Good location and even better prices. My husband and I made amazing memories here"
Reviewed on 28 Aug 2026
Waterside Inn
3761 Main St Chincoteague VA
The price is ฿2,892 per night from 27 Sept to 28 Sept
฿2,892
per night
27 Sept - 28 Sept
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 ...
9/10 Wonderful! (1,001 reviews)
"It’s a nice motel, but a little dated. The staff is great. The breakfast was just OK. It’s about 2 miles from the spot tours leave from and about 3 miles from things like miniature golf. The nearest bar and restaurant are about 1/2 mile away. I would definitely stay there again."
Reviewed on 27 Aug 2026
Key West Cottages
4251 Main Street Chincoteague VA
The price is ฿7,163 per night from 7 Sept to 8 Sept
฿7,163
per night
7 Sept - 8 Sept
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! (623 reviews)
"I love the location. It's like serenity. Will be returning"
Reviewed on 25 Aug 2026
Comfort Suites Chincoteague Island Bayfront Resort
4195 Main St Chincoteague VA
The price is ฿4,623 per night from 28 Sept to 29 Sept
฿4,623
per night
28 Sept - 29 Sept
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! (1,003 reviews)
"Clean place"
Reviewed on 27 Aug 2026
Marina Bay Hotel & Suites, an Ascend Collection Hotel
3801 Main St Chincoteague VA
The price is ฿3,045 per night from 7 Sept to 8 Sept
฿3,045
per night
7 Sept - 8 Sept
Stay at this business-friendly hotel in Chincoteague. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
Refuge Inn
7058 Maddox Blvd. Chincoteague VA
The price is ฿4,664 per night from 2 Sept to 3 Sept
฿4,664
per night
2 Sept - 3 Sept
Stay at this business-friendly hotel in Chincoteague. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
9.8/10 Exceptional! (1,001 reviews)
"This was an old fashioned, comfortable, great place to stay. We will definitely be back!"
Reviewed on 27 Aug 2026
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 Chincoteague Channel.
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 Assateague Lighthouse.
