Deep Hole Holiday Rentals

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Holiday Rentals in Deep Hole

Quaint Cottages Near Everything on Beach Road

9.4 out of 10, Exceptional, (39)
"Location, location, location"
Quaint Cottages Near Everything on Beach Road

The Blue Crab - Your Dream Vacation awaits you!

2.0 star property
10.0 out of 10, Exceptional, (11)
"This was our second stay at this property. Plenty of room for us and our 2 small dogs.The house is perfectly maintained. Bathrooms are up to date and the kitchen is well equiped.We will be back in the Fall."
The Blue Crab - Your Dream Vacation awaits you!

Sunrise Shore - Waterfront; Private pool & hot tub!

8.8 out of 10, Excellent, (34)
"Our family had a wonderful stay at Sunrise Shore. The house had a great location with beautiful views. The kitchen was well appointed and met all of needs. Our children really enjoyed the hot tub. There was plenty of room for our family of five. We hope to return someday soon!"
Sunrise Shore - Waterfront; Private pool & hot tub!

Waterfowl Watch Cottage - Chincoteague Island Quiet area,bikes, fall rates

10.0 out of 10, Exceptional, (15)
"Cozy and clean cottage with all the amenities. Close to everything!"
Waterfowl Watch Cottage - Chincoteague Island Quiet area,bikes, fall rates

Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!

9.4 out of 10, Exceptional, (12)
"Went for a guys trip and enjoyed it "
The price is AU$603
includes taxes & fees
7 Oct - 8 Oct
Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (440)
"Great place to stay!"
Key West Cottages

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (174)
"Super cute cottages for a weekend getaway! Right on the water too."
Blufin Bungalows & Marina

Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

9.6 out of 10, Exceptional, (42)
"We enjoyed our stay at Waterside. Location was perfect and host was very responsive to questions. A great rental for a few friends and/or family."
The price is AU$616
includes taxes & fees
8 Sept - 9 Sept
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

NEW PET FRIENDLY LISTING ALERT!!

9.4 out of 10, Exceptional, (16)
"Very clean, spacious and perfect for a stay with my girlfriend and two dogs! Definitely recommend!"
NEW PET FRIENDLY LISTING ALERT!!

Waterfront on Marsh Island!

8.8 out of 10, Excellent, (33)
"Visiting Chincoteague "
Waterfront on Marsh Island!

Cabin at Holdens Creek on Eastern Shore of VA

9.6 out of 10, Exceptional, (178)
"I like the fact that we were away from the hustle and bustle. The beaches are near by. And it was an overall great experience. Especially if you like secluded areas "
Cabin at Holdens Creek on Eastern Shore of VA

1BR Waterfront cottage with a view of the wild Chincoteague ponies!

9.6 out of 10, Exceptional, (13)
"3 night stay for our anniversary, beautiful view had a relaxing time! "
1BR Waterfront cottage with a view of the wild Chincoteague ponies!

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

10.0 out of 10, Exceptional, (57)
"Thank you so much for letting us stay at your house. The location was perfect for walking to restaurants and shops. Did a day at the wildlife refuge and spent some time on the beach. Plan to come back and enjoy another stay. "
The price is AU$437
includes taxes & fees
30 Sept - 1 Oct
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

9.6 out of 10, Exceptional, (50)
"Lovely , peaceful mini vacation"
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

At the Water's Edge - is there anywhere you'd rather be?!

10.0 out of 10, Exceptional, (48)
"Great property! Very clean"
At the Water's Edge - is there anywhere you'd rather be?!

The Hideaway Cottage

9.8 out of 10, Exceptional, (93)
"Just right for what we needed."
The Hideaway Cottage

Cozy Little Cottage on chincoteague island va.

9.6 out of 10, Exceptional, (46)
"Very cute little cottage, perfect amount of space for 2, has just about everything you'd need! Owner is helpful as well. Lots of places to eat within 15 mins"
Cozy Little Cottage on chincoteague island va.

Only 5 min to Assateague National Seashore!

9.6 out of 10, Exceptional, (18)
"Nice place. "
The price is AU$294
includes taxes & fees
8 Sept - 9 Sept
Only 5 min to Assateague National Seashore!

Make fabulous Vacation Memories at Family Tides Vacation Rental on Chincoteague

9.8 out of 10, Exceptional, (50)
"Great location and property for a peaceful and tranquil getaway."
Make fabulous Vacation Memories at Family Tides Vacation Rental on Chincoteague

Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS

7.0 out of 10, Good, (13)
"The Salty Sailor was an excellent, affordable, and pet friendly rental. Nice location on ridge rd next to Mr Baldys which is a must to try if you stay here. The rooms are a bit older but maintained well. I didn’t experience any of the conditions that were listed in the other reviews here. We would certainly stay here again."
Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS
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.
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Top Deep Hole Hotel Reviews

Find out more about Deep Hole

Find out more about Deep Hole

Everything you need to know about Deep Hole holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Deep Hole holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Deep Hole holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Deep Hole holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Deep Hole. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Deep Hole holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Deep Hole holiday rentals we have selected for you start as low as AU$294 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Deep Hole rentals

At Expedia, we put the best Deep Hole holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Deep Hole rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Deep Hole holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Deep Hole. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Deep Hole?

Yes, there are holiday rentals close to the most popular sights in Deep Hole, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Deep Hole has to offer?

Blufin Bungalows & Marina: This holiday home rental outside of Deep Hole is on the beach, and equipped with 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. Another good choice for your trip to Deep Hole is Quaint Cottages Near Everything on Beach Road .

How many holiday rentals are there in Deep Hole?

Expedia has 84 holiday rentals for your stay in Deep Hole.

What can I see and do in Deep Hole?

While exploring the area, visit family-friendly sights like Maui Jack's Waterpark, or get outside and enjoy nature at Oyster Bay. In the wider area, you’ll find Captain Timothy Hill House and Museum of Chincoteague.

What are holiday rentals like in Deep Hole?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Deep Hole. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a family trip.