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, (38)
"Location, location, location"
Quaint Cottages Near Everything on Beach Road

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, (10)
"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, (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!

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$635
includes taxes & fees
4 Sept - 5 Sept
Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (165)
"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, (428)
"Great place to stay!"
Key West Cottages

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

9.6 out of 10, Exceptional, (46)
"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 AU$663
includes taxes & fees
2 Sept - 3 Sept
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Waterfront on Marsh Island!

8.8 out of 10, Excellent, (32)
"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!

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 AU$487
includes taxes & fees
4 Sept - 5 Sept
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

Cabin at Holdens Creek on Eastern Shore of VA

9.6 out of 10, Exceptional, (172)
"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

NEW PET FRIENDLY LISTING ALERT!!

9.4 out of 10, Exceptional, (13)
"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!!

5 minutes to Assateague National Seashore!

8.8 out of 10, Excellent, (16)
"There was enough space for 3 adults and to children. The bathroom in the hall has not been updated. The shower was crudy and no towel rack. The spicket for shower/bath in the 2nd bathroom was almost impossible to use. The rental was okay."
The price is AU$306
includes taxes & fees
16 Sept - 17 Sept
5 minutes to Assateague National Seashore!

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 AU$700
includes taxes & fees
24 Aug - 25 Aug
The purple door at the bay.

Featured DC magazine 10 BEST/Waterview CLOSEST community to BEACH 3 decks.

10.0 out of 10, Exceptional, (144)
"The house and location are very nice"
Featured DC magazine 10 BEST/Waterview CLOSEST community to BEACH 3 decks.

Only 5 min to Assateague National Seashore!

9.6 out of 10, Exceptional, (18)
"Nice place. "
The price is AU$354
includes taxes & fees
9 Sept - 10 Sept
Only 5 min to Assateague National Seashore!

The Happy Crab - Waterfront on Chincoteague Island!

9.0 out of 10, Wonderful, (14)
"Really enjoyed the place, beautiful sunrises, great little island and food "
The Happy Crab - Waterfront on Chincoteague Island!

Daisey Cottage - Pet friendly w/ Fenced yard!

9.6 out of 10, Exceptional, (52)
"Will stay again if available on our next trip"
Daisey Cottage - Pet friendly w/ Fenced yard!

Stunning waterfront panoramic view getaway house

10.0 out of 10, Exceptional, (53)
"The roundhouse was amazing on many levels, figuratively and literally. There are many creature, comforts throughout this sprawling home and the views were serene and relaxing, and the couches and beds were comfy! And the host was very helpful and accommodating. Highly recommend would definitely stay here again."
The price is AU$811
includes taxes & fees
3 Sept - 4 Sept
Stunning waterfront panoramic view getaway house
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 TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop and a microwave. Some other top choices in Deep Hole are Quaint Cottages Near Everything on Beach Road and 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.