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, (36)
"Location, location, location"
Quaint Cottages Near Everything on Beach Road

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

9.8 out of 10, Exceptional, (11)
"Went for a guys trip and enjoyed it "
Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!

An Unfettered View - Beautiful ranch w/ boat dock!

10.0 out of 10, Exceptional, (20)
"We really enjoyed the property. It feels very much like a quaint seaside cottage inside, right down to the pocket doors! The neighborhood is a bit removed from the main part of town, but was exceedingly quiet. Would stay again!"
An Unfettered View - Beautiful ranch w/ boat dock!

Oyster Bay Hideaway on Chincoteague Island!

10.0 out of 10, Exceptional, (9)
"We thoroughly enjoyed the home, dock, location, and overall stay."
Oyster Bay Hideaway on Chincoteague Island!

The Blue Crab - Your Dream Vacation awaits you!

2.0 star property
10.0 out of 10, Exceptional, (9)
"This house is very convenient to anything you would want on the island. The kitchen is very well equipped as well! Thanks. "
The Blue Crab - Your Dream Vacation awaits you!

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (154)
"It was a very clean, comfortable place to stay in on vacation "
Blufin Bungalows & Marina

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (407)
"We had wonderful stay. Everything about this resort was perfect. "
Key West Cottages

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

9.6 out of 10, Exceptional, (45)
"Lovely , peaceful mini vacation"
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

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 NZ$808
includes taxes & fees
21 Aug - 22 Aug
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

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

10.0 out of 10, Exceptional, (52)
"An instant nervous system reset."
The price is NZ$693
includes taxes & fees
17 Aug - 18 Aug
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

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?!

Waterfront on Marsh Island!

9.0 out of 10, Wonderful, (29)
"Small Cozy condo for couples. Very quiet and relaxing with great sunrises and sunsets! Great location with being on the water!"
Waterfront on Marsh Island!

5 minutes to Assateague National Seashore!

9.2 out of 10, Wonderful, (13)
"Very nice stay, no complaints "
5 minutes to Assateague National Seashore!

Cabin at Holdens Creek on Eastern Shore of VA

9.6 out of 10, Exceptional, (169)
"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

Daisey Cottage - Pet friendly w/ Fenced yard!

9.6 out of 10, Exceptional, (51)
"Will stay again if available on our next trip"
Daisey Cottage - Pet friendly w/ Fenced yard!

NEW PET FRIENDLY LISTING ALERT!!

9.2 out of 10, Wonderful, (10)
"Lovely home right on the river- fishing to your hearts content Clean, lots to do very peaceful!!! Would definitely come back! Mia is great to work with"
NEW PET FRIENDLY LISTING ALERT!!

The Happy Crab - Waterfront on Chincoteague Island!

9.2 out of 10, Wonderful, (13)
"Really enjoyed the place, beautiful sunrises, great little island and food "
The Happy Crab - Waterfront on Chincoteague Island!

Cozy Little Cottage on chincoteague island va.

9.6 out of 10, Exceptional, (42)
"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.

Stunning waterfront panoramic view getaway house

10.0 out of 10, Exceptional, (53)
"The Captain’s Roundhouse was a great place to spend a relaxing week. The view is terrific and the kitchen is newly renovated."
The price is NZ$1,360
includes taxes & fees
6 Aug - 7 Aug
Stunning waterfront panoramic view getaway house

Only 5 min to Assateague National Seashore!

9.6 out of 10, Exceptional, (17)
"Nice place. "
Only 5 min to Assateague National Seashore!
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

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 Smart 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 An Unfettered View - Beautiful ranch w/ boat dock!.

How many holiday rentals are there in Deep Hole?

Expedia has 83 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.