Deep Hole Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in Deep Hole

Waterside Inn
Waterside Inn
2 out of 5
3761 Main St, Chincoteague, VA
Fully refundableReserve now, pay when you stay
The price is S$89 per night from 2 Dec to 3 Dec
S$89
includes taxes & fees
2 Dec - 3 Dec
8.8/10 Excellent! (1,001 reviews)
"Thank you : me. And wife happy about this place. ⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️⭐️ stars."

Reviewed on 19 Nov,2024

Waterside Inn
Key West Cottages
Key West Cottages
3 out of 5
4251 Main Street, Chincoteague, VA
The price is S$155 per night from 26 Nov to 27 Nov
S$155
includes taxes & fees
26 Nov - 27 Nov
9.6/10 Exceptional! (293 reviews)
"I love how quiet and relaxing the property was this time of year. Amazing views. I look forward to returning soon!"

Reviewed on 10 Nov,2024

Key West Cottages
Comfort Suites Chincoteague Island Bayfront Resort
Comfort Suites Chincoteague Island Bayfront Resort
2.5 out of 5
4195 Main St, Chincoteague, VA
Fully refundableReserve now, pay when you stay
The price is S$142 per night from 22 Dec to 23 Dec
S$142
includes taxes & fees
22 Dec - 23 Dec
9.4/10 Exceptional! (1,000 reviews)
"Clean rooms and super nice staff"

Reviewed on 14 Nov,2024

Comfort Suites Chincoteague Island Bayfront Resort
See all 738 properties in Deep Hole
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

How much does a Deep Hole holiday package cost?
From as little as . Yes, you read that correctly. Our Deep Hole packages are the quickest way to make your budget stretch further. Combine your preferred hotels, flights and car rentals and discover this wonderful destination.
How do I get a cheap travel package to Deep Hole?
Think of all the fabulous things you could do in Deep Hole with extra cash in your pocket. Watch your savings stack up when you bundle your airfare and hotel bookings into a Deep Hole holiday package. You have loads of choice when you book with Expedia too. In fact, you can select from more than 550 airlines and 1,000,000 properties around the world. Whether you’re taking a holiday with the whole family or flying solo, planning a getaway to Deep Hole is better with a package.
Where should I stay in Deep Hole?
With popular attractions like Maui Jacks Waterpark and Robert N. Reed Downtown Waterfront Park in this area, try to find a hotel near either one. Oyster Bay is another Deep Hole sight that draws in the crowds.
What are the top hotels in Deep Hole?
Get your holiday off to an excellent start by booking a stay at Newly Renovated Pet Friendly Beach House Near Dining. It’s one of most sought-after properties in Deep Hole. Another leading option is Pearl In The Pines: Kayaks.
How far in advance should I book my Deep Hole holiday?
While prices do change, we generally recommend reserving your seat as soon as possible. Most international airfares can be compared on Expedia up to 12 months in advance. If circumstances have left you booking last minute, you might still be in luck. Cheaper tickets to Deep Hole sometimes appear only weeks before departure.
What does an Expedia Deep Hole travel package include?
Flights, hotels and rental cars — we’ve got them well covered. With Expedia, you can shape your Deep Hole package just the way you want. All you have to do is determine exactly what you need. Once you’ve made your booking, you can add on extras like tours and activities. The more you bundle, the bigger the savings!
What should I know before booking a Deep Hole travel package?
Booking all the parts of your getaway together is a great way to save. Combine car rentals, airfares and hotels into a neat little package. But hotels aren’t your only option. Expedia features all sorts of properties, including holiday rentals like beachside villas and city residences. You’ve got loads of choices!
Can I choose my airline with a Deep Hole Expedia holiday package?
You can, and with more than 550 airlines to pick from globally, you’re spoiled for choice. Have a look through the available options and find out which airline fits your budget and needs.
If I'm not able to travel, can I cancel my Deep Hole holiday package?
You can cancel your Deep Hole booking if your travel plans have changed. Whether you’ll be charged a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.