Find hotels in Deep Hole, VA from CA $119

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May 14 - May 15
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May 15 - May 16
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May 17 - May 19
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May 24 - May 26

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Top 10 Deep Hole hotels and places to stay

Exterior
Small cottage for those little getaways
10.0 out of 10, Exceptional, (89)
"Enjoyed our time great bang for the buck."
Small cottage for those little getaways
Property grounds
Assateague Inn 107 on Chincoteague!
10.0 out of 10, Exceptional, (2)
"Quiet, clean, everything worked; not sure about tv in bedroom as we don’t typically watch in there."
The price is CA $137
CA $258 total
includes taxes & fees
May 21 - May 22
Assateague Inn 107 on Chincoteague!
Beach nearby
The Hideaway Cottage
10.0 out of 10, Exceptional, (68)
"Enjoy Don's cottage - the screened in patio was lovely to enjoy coffee and do some light office work. Kitchen had enough of everything to heat or prepare simple meals. Hot water was plentiful and pressure good in the shower. Bed was comfortable. The area is very quiet at night but during the day there is a small business next door that you do hear light people chatter/deliveries. I would say this location is like a modern cabin - just enough of everything but still feels rustic."
The Hideaway Cottage
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Fridge, microwave, oven, stovetop
Kick back and relax at “Knot Stressed” in total comfort.
10.0 out of 10, Exceptional, (18)
"We were visiting family in Pocomoke City and this was the perfect place for us to stay. Comfortable beds. Bright and spacious. Great area! We enjoyed nice walks in the morning."
Kick back and relax at “Knot Stressed” in total comfort.
Grand Room, 1 King Bed
Chanceford Hall Bed & Breakfast
2.0 star property
10.0 out of 10, Exceptional, (3)
"A great experience! The home is historical, the owners are a delight, it was very clean and the food was delicious!!!! Highly recommend "
Chanceford Hall Bed & Breakfast
TV
Bliss on the Bay - Perfect Beach Getaway
10.0 out of 10, Exceptional, (2)
"Clean, quaint, quiet! Just what we wanted!"
Bliss on the Bay - Perfect Beach Getaway
View from property
Camping at its best
10.0 out of 10, Exceptional, (12)
"It was a lot nicer than we thought it would be. The owners are fantastic people. We hope to stay again next year. The pool and boat ramps are great. The store is well stocked. We would recommend it to everyone. Except the weeks we want it. Lol"
Camping at its best
Fridge, microwave, oven, stovetop
Breezy Corner in the heart of Chincoeague!
10.0 out of 10, Exceptional, (1)
"Great place to make memories. Everyone in family liked it. Cozy spaces!"
Breezy Corner in the heart of Chincoeague!
Exterior
Hampton Inn & Suites Chincoteague Waterfront
2.5 star property
9.8 out of 10, Exceptional, (559)
"Everything "
The price is CA $208
CA $234 total
includes taxes & fees
May 27 - May 28
Hampton Inn & Suites Chincoteague Waterfront
Property grounds
Only 5 min to Assateague National Seashore!
9.8 out of 10, Exceptional, (6)
"Check in process was easy, unit was as described, very clean. Perfect location. Would definitely request the same unit"
The price is CA $137
CA $258 total
includes taxes & fees
May 21 - May 22
Only 5 min to Assateague National Seashore!
Fridge, microwave, oven, stovetop
Duck's Delight - Pet friendly rentals within walking distance to Maddox Blvd!
9.8 out of 10, Exceptional, (116)
"This house was perfect for our family. We found everything we needed to cook meals. Nice big washing machine and clothes dryer. Loved eating breakfast on the screened in porch. Quiet neighborhood, very close to many restaurants. Plenty of hot water for showers. VERY clean. Comfortable seating, beds were comfy too. Super fast response from the owner when I had a question. Wifi was strong enough for 2 teenagers and 3 adults."
Duck's Delight - Pet friendly rentals within walking distance to Maddox Blvd!
Front of property
Garden and Sea Inn
3.5 star property
9.6 out of 10, Exceptional, (23)
"The place is beautiful!!! The proprietor (Grace) was very sweet and helpful. If ever I come back to this area, this would be my stay of choice!! First class and lovely!"
The price is CA $299
CA $330 total
includes taxes & fees
May 15 - May 16
Garden and Sea Inn
Property grounds
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi
9.6 out of 10, Exceptional, (125)
"We only had a short stay to relax away from work but the weather didn’t cooperate (rainy and windy). Luckily the cottage was cozy and we enjoyed our books and each other. Only suggestion, need a sponge or brush to help in cleaning up after meals. Would definitely recommend to others"
The price is CA $310
CA $600 total
includes taxes & fees
May 15 - May 16
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi
Pool
Hidden Gem ! Clean & Cozy and Family Friendly !
9.6 out of 10, Exceptional, (49)
"The house is in a very nice community campground! It made me miss camping and the restaurant there is super good and there’s even a crab guy within the park that will cook up your crabs that you buy from him and there’s a launch place for your boat. So many things but not close to many stores, very peaceful and relaxing!!!!"
Hidden Gem ! Clean & Cozy and Family Friendly !
Interior
Caprecia's Castle-Waterfront w/shared crabbing/fishing pier
9.4 out of 10, Exceptional, (3)
"If taking a vacation to Chincoteague, there is no better location than this small island. Easy parking and traveling in and out of this property. Well worth it."
Caprecia's Castle-Waterfront w/shared crabbing/fishing pier
Exterior
Island Resort
2.0 star property
9.2 out of 10, Wonderful, (382)
"Loved it here! Hotel was clean and friendly staff. Had a beautiful view of the bay too. The continental breakfast was great as well. We will definitely be returning. "
The price is CA $205
CA $230 total
includes taxes & fees
May 22 - May 23
Island Resort
Property grounds
5 minutes to Assateague National Seashore!
9.2 out of 10, Wonderful, (5)
"Great location on Chincoteague Island, in between downtown and the beach. Quiet property. Lovely path to small deck, just beware of droppings everywhere!😂 We booked a 2 bedroom through Vrbo, but got there to find only one. Owner knows so this discrepancy should be rectified.Definitely will come back:)"
The price is CA $137
CA $258 total
includes taxes & fees
May 22 - May 23
5 minutes to Assateague National Seashore!
Microwave, stovetop, coffee/tea maker, toaster
Only 5 min. from the Beach!
9.2 out of 10, Wonderful, (5)
"The suite was cute and well stocked!"
The price is CA $148
CA $272 total
includes taxes & fees
May 27 - May 28
Only 5 min. from the Beach!
Aerial view
Marina Bay Hotel & Suites, Ascend Hotel Collection
2.5 star property
9.0 out of 10, Wonderful, (809)
"Property close to carnival grounds although we aren’t here for pony penning Rooms are nice and clean Staff was very nice at front desk Hotel is a bit newer. "
The price is CA $183
CA $220 total
includes taxes & fees
May 22 - May 23
Marina Bay Hotel & Suites, Ascend Hotel Collection
Outdoor pool
Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront
2.5 star property
9.0 out of 10, Wonderful, (451)
"Pleasant staff, very clean, nice hot breakfast"
The price is CA $212
CA $238 total
includes taxes & fees
May 19 - May 20
Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront
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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.

Frequently asked questions

What's the best place to stay in Deep Hole?

Based on Expedia's traveler preferences, Quaint Cottages Near Everything on Beach Road is a top place to stay in Deep Hole. Other good choices for your stay include Oyster Bay Hideaway on Chincoteague Island! and ★Jay’s Waterfront Retreat: Private Dock-Fire-pit-Kayaks & Bikes Inc.-Beach★. See all available top hotels, or vacation rentals in Deep Hole.

What are some of the best vacation rentals in Deep Hole?

Blufin Bungalows & Marina: You might want to consider this vacation home rental near Deep Hole, which has free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and a microwave. Other favorite homes for rent in Deep Hole are Quaint Cottages Near Everything on Beach Road and Oyster Bay Hideaway on Chincoteague Island!. See all vacation rentals in Deep Hole.

If I need to cancel my hotel reservation in Deep Hole, will I receive a refund?

Yes! You'll find that most room reservations are fully refundable if you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Deep Hole.

Where can I learn more about changing or cancelling my trip to Deep Hole?

To access more information about changing or cancelling your trip to Deep Hole, click here.

What are some accommodations with pools in Deep Hole?

Comfort Suites Chincoteague Island Bayfront Resort: Features an indoor pool, an outdoor pool, and a snack bar/deli. Refuge Inn and Waterside Inn are a couple of other choices that offer an onsite pool. View all hotels with pools in Deep Hole.

What's the most popular hotel in Deep Hole with a water park on-site or close by?

Jays Waterfront Retreat: Fire-pit-kayaks-bikes-beach-pet Friendly is a popular vacation home featuring in-room kitchens and water park access. You'll find Maui Jack's Waterpark within 5 minutes by car.

What's it like to stay in Deep Hole?

Visitors to Deep Hole are sure to find plenty to explore and enjoy. In Deep Hole, there are 81 hotels and other accommodations to choose from. Find out more about Deep Hole.

What should I see while I'm in Deep Hole?

A favorite place to visit is Oyster Bay. You'll also find Maui Jack's Waterpark and Chincoteague National Wildlife Refuge in the area. Check out what more to see and do in Expedia's Deep Hole guide.

What's the weather like in Deep Hole?

The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 43°F. Average annual precipitation for Deep Hole is 48 inches.