Deep Hole Vacation Rentals

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Check prices for these dates

Tonight
Sep 1 - Sep 2
Tomorrow
Sep 2 - Sep 3
This weekend
Sep 5 - Sep 7
Next weekend
Sep 12 - Sep 14

Vacation Rentals in Deep Hole

Quaint Cottages Near Everything on Beach Road
Exterior

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!
Fridge, microwave, oven, stovetop

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!
Fridge, microwave, oven, stovetop

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
Smart TV, books

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
Key West Cottages
Exterior

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (438)
"Great place to stay!"
Key West Cottages
Blufin Bungalows & Marina
Exterior

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (169)
"excellent place to stay on the water"
Blufin Bungalows & Marina
NEW PET FRIENDLY LISTING ALERT!!
Smart TV, fireplace

NEW PET FRIENDLY LISTING ALERT!!

9.4 out of 10, Exceptional, (16)
"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!!
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Exterior

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 ￥15,440
￥59,120 total
includes taxes & fees
Sep 3 - Sep 4
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
The purple door at the bay.
Terrace/patio

The purple door at the bay.

9.2 out of 10, Wonderful, (51)
"Property was slightly run down and had no driveway (just grass). It was in a great neighborhood with a beautiful view. We had to take the trash 15 minutes south when leaving (in the opposite direction of home for us). It was good enough for us to relax and cook but a slight bit expensive for its outdated condition though."
The price is ￥23,160
￥66,257 total
includes taxes & fees
Sep 14 - Sep 15
The purple door at the bay.
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
Beach

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

9.6 out of 10, Exceptional, (48)
"Lovely , peaceful mini vacation"
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
Waterfront on Marsh Island!
Interior

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
Interior

Cabin at Holdens Creek on Eastern Shore of VA

9.6 out of 10, Exceptional, (177)
"Beautiful cabin situated at the back of a farm, very peaceful. Very spacious and inviting. Only a half hour to Chincoteague and an hour to Ocean City. Nice porch with a swing and 2 chairs to sit out in the morning with a cup of coffee (coffee maker provided). We loved having a pool table for our evening entertainment. Only thing we didn't like was the very tiny kitchen, absolutely no counter space at all :( "
Cabin at Holdens Creek on Eastern Shore of VA
1BR Waterfront cottage with a view of the wild Chincoteague ponies!
Pool

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!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (55)
"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 ￥16,176
￥40,460 total
includes taxes & fees
Sep 29 - Sep 30
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Make fabulous Vacation Memories at Family Tides Vacation Rental on Chincoteague
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

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
The Brass Crab - Check in/out any day!
Fridge, microwave, oven, stovetop

The Brass Crab - Check in/out any day!

10.0 out of 10, Exceptional, (151)
"The Brass Crab is the perfect family place to stay. Thank you for all the extras."
The Brass Crab - Check in/out any day!
Only 5 min to Assateague National Seashore!
Terrace/patio

Only 5 min to Assateague National Seashore!

9.6 out of 10, Exceptional, (18)
"Nice place. "
The price is ￥15,293
￥28,782 total
includes taxes & fees
Sep 9 - Sep 10
Only 5 min to Assateague National Seashore!
At the Water's Edge - is there anywhere you'd rather be?!
Interior

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?!
5 minutes to Assateague National Seashore!
Flat-screen TV

5 minutes to Assateague National Seashore!

8.8 out of 10, Excellent, (17)
"The condo was perfect for my girlfriend and I, very private location and nice boardwalk by the creek"
The price is ￥14,798
￥27,738 total
includes taxes & fees
Sep 15 - Sep 16
5 minutes to Assateague National Seashore!
The Hideaway Cottage
Beach nearby

The Hideaway Cottage

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

Search for holiday rentals in Deep Hole on Expedia! You can easily find your home rentals, villas, holiday apartments in Deep Hole using one of the methods below:

  • View our selection of featured holiday rentals in Deep Hole
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  • Enter your travel dates to view the best deals on holiday rentals in Deep Hole while they last

Look no further and take a look at our great range of rental properties in Deep Hole!

Frequently asked questions

Can I find a vacation rental in Deep Hole?

Yes, we offer vacation rentals close to popular sights in Deep Hole, or you can go with a more remote option if you want a relaxing place to stay.

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

Blufin Bungalows & Marina: Located near Deep Hole, this vacation home rental 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 vacation rentals are there in Deep Hole?

Expedia has 84 vacation 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 larger area, you’ll find Captain Timothy Hill House and Museum of Chincoteague.

What are vacation rentals like in Deep Hole?

Vacation rentals are private accommodations you can stay in for a couple days or more in Deep Hole. Vacation rentals feature amenities like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a small group gathering.