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Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

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Our top choices for Deep Hole hotels

A waterfront hotel with a wooden deck, grassy lawn, and multiple balconies.

1. Comfort Suites Chincoteague Island Bayfront Resort

Comfort Suites Chincoteague Island Bayfront Resort
2.5 star property
Downtown Chincoteague, 1.2 mi from Deep Hole
9.6 out of 10, Exceptional, (1,005 reviews)
"Best room on the island"
United States
Jeffrey
$103 nightly
The price is $117
Nov 24 - Nov 25
Total with taxes and fees
Comfort Suites Chincoteague Island Bayfront Resort
A hot tub in a room with large windows overlooking a water body and grassy area.

2. Waterside Inn

Waterside Inn
2.0 star property
Downtown Chincoteague, 1.8 mi from Deep Hole
9.0 out of 10, Wonderful, (1,007 reviews)
"Cute and comfortable room with a balcony overlooking the chincoteague bay, Great views and a convenient location downtown with lots to do nearby. Staff was friendly and helpful, breakfast was good and we were even able to get it to go."
United States
Reina
$56 nightly
The price is $63
Nov 1 - Nov 2
Total with taxes and fees
Waterside Inn
A waterfront hotel with multiple balconies, a dock, and a calm water body.

3. Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront

Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront
3.0 star property
Downtown Chincoteague, 1.5 mi from Deep Hole
9.2 out of 10, Wonderful, (653 reviews)
"Great staff, beautiful view of the bay & a nice hot breakfast buffet"
United States
Dianne
$119 nightly
The price is $134
Nov 1 - Nov 2
Total with taxes and fees
Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront
A spacious indoor area with a white sofa set, round tables, and large windows offering views of the outdoors.

4. Spark by Hilton Chincoteague Island

Spark by Hilton Chincoteague Island
2.5 star property
Piney Island, 1 mi from Deep Hole
9.6 out of 10, Exceptional, (827 reviews)
"The staff and amenities were excellent at this hotel. The views were also beautiful. Right across the street or all the shops you need for peeing suits, renting bikes, etc."
United States
Patricia
$84 nightly
The price is $95
Nov 5 - Nov 6
Total with taxes and fees
Spark by Hilton Chincoteague Island
A multi-story hotel with a blue roof, located near a marina with boats docked.

5. Marina Bay Hotel & Suites, an Ascend Collection Hotel

Marina Bay Hotel & Suites, an Ascend Collection Hotel
2.5 star property
Downtown Chincoteague, 1.8 mi from Deep Hole
9.0 out of 10, Wonderful, (1,003 reviews)
"Nice convenient location. Pool etc recently closed due to season. Pretty view of the sound. Staff helpful and friendly. Breakfast ok but not deserving of rave review"
United States
Joset
$93 nightly
The price is $105
Nov 2 - Nov 3
Total with taxes and fees
Marina Bay Hotel & Suites, an Ascend Collection Hotel
A covered outdoor area with a table and chairs, overlooking a body of water with a bridge in the distance.

6. Hampton Inn & Suites Chincoteague Waterfront

Hampton Inn & Suites Chincoteague Waterfront
2.5 star property
Downtown Chincoteague, 1.3 mi from Deep Hole
9.8 out of 10, Exceptional, (830 reviews)
"Great view, lovely staff, delicious breakfast !"
United States
Jessica
$102 nightly
The price is $114
Nov 10 - Nov 11
Total with taxes and fees
Hampton Inn & Suites Chincoteague Waterfront
A hotel room with a bed, a sofa, a desk, and a radiator.

7. Chincoteague Inn

Chincoteague Inn
2.0 star property
Downtown Chincoteague, 0.8 mi from Deep Hole
8.6 out of 10, Excellent, (1,001 reviews)
"Large clean room, easy check in and out, great location and value for money"
United States
Amy
$79 nightly
The price is $89
Oct 27 - Oct 28
Total with taxes and fees
Chincoteague Inn
A swimming pool with lounge chairs and a beach ball.

8. Refuge Inn

Refuge Inn
3.0 star property
Piney Island, 1 mi from Deep Hole
9.8 out of 10, Exceptional, (1,002 reviews)
"There are so many things we loved about this place, location, breakfast amenities, the rooms were clean and of course the ponies on the property. We would definitely stay here again."
United States
Karen
$124 nightly
The price is $139
Nov 1 - Nov 2
Total with taxes and fees
Refuge Inn
A spacious dining area with multiple tables and chairs, a television mounted on an orange wall, and a statue in the center.

9. Days Inn by Wyndham Chincoteague Island

Days Inn by Wyndham Chincoteague Island
2.0 star property
Piney Island, 0.9 mi from Deep Hole
6.8 out of 10, (1,001 reviews)
"The place was clean, reasonably priced, and the owner was very helpful. The beds were very comfortable and breakfast was great. Would definitely stay again."
United States
Laura
$71 nightly
The price is $80
Oct 30 - Oct 31
Total with taxes and fees
Days Inn by Wyndham Chincoteague Island
A pool area with a building that has a covered patio and a gazebo.

10. Atlantic Shores Inn and Suites

Atlantic Shores Inn and Suites
2.0 star property
Downtown Chincoteague, 0.8 mi from Deep Hole
7.6 out of 10, Good, (1,001 reviews)
"Everything was great for an overnight stay, a bit off Rte 13, since we were just traveling through, but great staff and fine rustic room"
United States
Dave
$82 nightly
The price is $92
Nov 26 - Nov 27
Total with taxes and fees
Atlantic Shores Inn and Suites
A compact kitchenette with a built-in refrigerator, a coffee maker, and a sink with a granite countertop.

11. sea shell motel

sea shell motel
2.0 star property
1.3 mi from Deep Hole
$48 nightly
The price is $54
Nov 1 - Nov 2
Total with taxes and fees
sea shell motel
A large two-story house with a balcony, a covered patio, and a view of the water.

12. Island Resort

Island Resort
2.0 star property
Downtown Chincoteague, 1 mi from Deep Hole
9.2 out of 10, Wonderful, (488 reviews)
"Clean and comfortable rooms, beautiful views. Friendly staff"
United States
Brenda
$130 nightly
The price is $146
Oct 27 - Oct 28
Total with taxes and fees
Island Resort
Beach

13. Maddox Inn

Maddox Inn
2.0 star property
Downtown Chincoteague, 1 mi from Deep Hole
7.4 out of 10, Good, (843 reviews)
"This is an old-style, mom and pop hotel with lots of character, and the rooms are decent. I enjoyed my stay."
United States
Jeffrey
$83 nightly
The price is $93
Nov 26 - Nov 27
Total with taxes and fees
Maddox Inn
A waterfront house with a balcony, dock, and a view of the water.

14. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague, 1.2 mi from Deep Hole
9.8 out of 10, Exceptional, (667 reviews)
"First time here and we absolutely loved it."
United States
Melissa
$211 nightly
The price is $237
Nov 25 - Nov 26
Total with taxes and fees
Key West Cottages
A modern lobby with a reception desk, seating area, and artwork on the walls.

15. Best Western Plus Pocomoke City

Best Western Plus Pocomoke City
2.5 star property
14.7 mi from Deep Hole
8.6 out of 10, Excellent, (1,000 reviews)
"Bed was comfortable, everything was clean, staff are very helpful and nice."
United States
Rachel
$105 nightly
The price is $117
Nov 22 - Nov 23
Total with taxes and fees
Best Western Plus Pocomoke City
A spacious lobby with a curved reception desk, a seating area with a sofa, and a patterned carpet.

16. Econo Lodge Pocomoke City Hwy 13

Econo Lodge Pocomoke City Hwy 13
2.0 star property
12.1 mi from Deep Hole
5.6 out of 10, (857 reviews)
"This is a place suitable for people on a tighter budget."
United States
Rong
$59 nightly
The price is $66
Nov 24 - Nov 25
Total with taxes and fees
Econo Lodge Pocomoke City Hwy 13
A lobby with a tiled floor, a vending machine, a refrigerator, and a lamp.

17. Motel 6 Pocomoke City, MD

Motel 6 Pocomoke City, MD
2.0 star property
13 mi from Deep Hole
5.4 out of 10, (509 reviews)
"All the staff here is amazing. They are friendly and very friendly to help you."
United States
Debra
$70 nightly
The price is $78
Oct 29 - Oct 30
Total with taxes and fees
Motel 6 Pocomoke City, MD
A large, two-story house with a porch and a garden with purple flowers.

18. Garden and Sea Inn

Garden and Sea Inn
3.5 star property
10.2 mi from Deep Hole
9.4 out of 10, Exceptional, (30 reviews)
"Grace was an unbelievable host...saw to our needs, can not say enough POSITIVE about this B&B....would love to find an excuse to return. "
United States
Douglas
$209 nightly
The price is $231
Oct 27 - Oct 28
Total with taxes and fees
Garden and Sea Inn
A reception area with a wooden cabinet, a green sofa, and a black reception desk.

19. Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD
2.0 star property
13 mi from Deep Hole
7.6 out of 10, Good, (95 reviews)
"We stayed for one night and it was definitely a great place for it plus we got lost on where our room is and even though it was late the guy was very nice to still be nice and help us out(:"
United States
Brandon
$75 nightly
The price is $84
Nov 1 - Nov 2
Total with taxes and fees
Studio 6 Suites Pocomoke City, MD
A brick pathway leading to a pool area with a fence and potted plants.

20. Cypress River Inn & Spa

Cypress River Inn & Spa
5.0 star property
16.7 mi from Deep Hole
8.4 out of 10, Very good, (7 reviews)
"I fell in love with the charm of this Inn, I can't wait for the restaurant to be up and running so I can come back and stay."
United States
Hans
$203 nightly
The price is $227
Nov 26 - Nov 27
Total with taxes and fees
Cypress River Inn & Spa
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.
View all properties

Compare popular hotels in Deep Hole

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet friendly
WiFi included
A waterfront hotel with a wooden deck, grassy lawn, and multiple balconies.
Comfort Suites Chincoteague Island Bayfront Resort
2.5 star property
9.6
Exceptional
1,005 reviews
View
A covered outdoor area with a table and chairs, overlooking a body of water with a bridge in the distance.
Hampton Inn & Suites Chincoteague Waterfront
2.5 star property
9.8
Exceptional
830 reviews
View
A waterfront hotel with multiple balconies, a dock, and a calm water body.
Fairfield Inn & Suites by Marriott Chincoteague Island Waterfront
3.0 star property
9.2
Wonderful
653 reviews
View
A waterfront house with a balcony, dock, and a view of the water.
Key West Cottages
3.0 star property
9.8
Exceptional
667 reviews
View
A swimming pool with lounge chairs and a beach ball.
Refuge Inn
3.0 star property
9.8
Exceptional
1,002 reviews
View

Hotels recommended for families in Deep Hole

A row of three-story townhouses with a front porch, a small garden, and a clear blue sky.

Central Location~Walk 2 Dining! Beach Pass & Gear!

Central Location~Walk 2 Dining! Beach Pass & Gear!
Deep Hole
10.0 out of 10, Exceptional, (10)
$257 nightly
The price is $279
Oct 27 - Oct 28
Total with taxes and fees
Central Location~Walk 2 Dining! Beach Pass & Gear!

Where to stay in Deep Hole

Find the best Deep Hole areas and neighborhoods for the activities you enjoy most.
A group of horses grazing in a lush green field with a river in the foreground.
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.

A coastal landscape with a clear blue sky, a calm sea, and a marshy area with water reflecting the sky.

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.

Top Deep Hole Hotel Reviews

Waterside Inn

Waterside Inn

10/10 Excellent
"We visited in the off-season but were very pleased with the appearance and convenience of the property. Room was clean and had a lot of room. We booked a water view room with a balcony and 2 beds. We were very pleased with the size of the room and the bathroom. The indoor hot tub was nice too. We have been to Chincoteague many times and this was our first time staying at this hotel. We will most definitely be staying here again. Highly recommended."
Bill 1-night trip
Posted 4 hours ago
Waterside Inn

Frequently asked questions

When is the best time to go to Deep Hole?
When planning your trip to Deep Hole, Virginia, the best time to visit is during the shoulder seasons of spring (April to May) and fall (September to October).

These months offer pleasant temperatures, generally ranging from the mid-60s to high 70s Fahrenheit, which are ideal for outdoor activities like hiking, fishing, and exploring the natural surroundings without the intense heat and humidity of summer. You'll also find the natural beauty of the area enhanced by blooming wildflowers in spring or the vibrant fall foliage.

Couples looking for a tranquil getaway will particularly appreciate these times. The quieter atmosphere allows for more intimate experiences, whether it's a peaceful walk along the trails or enjoying a meal at one of the local establishments without the larger crowds of peak summer.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Deep Hole.
How much is the nightly rate at a Deep Hole hotel?
Prices for hotels in Deep Hole often vary, but you can find a great deal on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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