Deep Hole Vacation Rentals

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Vacation Rentals in Deep Hole

Quaint Cottages Near Everything on Beach Road
Exterior
Quaint Cottages Near Everything on Beach Road
9.6 out of 10, Exceptional, (25)
"Quiet neighborhood. Conveniently close to the refuge and restaurants."
Quaint Cottages Near Everything on Beach Road
Oyster Bay Hideaway on Chincoteague Island!
Fridge, microwave, oven, stovetop
Oyster Bay Hideaway on Chincoteague Island!
10.0 out of 10, Exceptional, (3)
"Clean and convenient Highly recommend"
Oyster Bay Hideaway on Chincoteague Island!
Jay’s Retreat: EV Charger-Kayaks-Bikes-Fire Pit-Private Dock-Pets Ok-Crabbing
Property grounds
Jay’s Retreat: EV Charger-Kayaks-Bikes-Fire Pit-Private Dock-Pets Ok-Crabbing
10.0 out of 10, Exceptional, (189)
"The hosts were very communicative. We made good use of the propane grill and ran out. The host was there with a new tank within 5 minutes. The kitchen was very well equipped with everything needed to cook and a good supply of a variety of spices. The hot water on demand was welcome for warm showers on chilly nights."
Jay’s Retreat: EV Charger-Kayaks-Bikes-Fire Pit-Private Dock-Pets Ok-Crabbing
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Sunrise Shore - Waterfront; Private pool & hot tub!
Fridge, microwave, oven, stovetop
Sunrise Shore - Waterfront; Private pool & hot tub!
8.8 out of 10, Excellent, (31)
"We had my bachelorette party at this property and it was PERFECT. The views and location are unbeatable and the hot tub, pool, and easy water access provided endless hours of fun. We also appreciated the multitude of beds and cots available as well as the plentiful sheets, towels, and bedding. The communication was effortless and easy and the team was very responsive to our needs. They even opened the pool earlier than their typical schedule. NOTE: if you're renting this in the spring or fall,...
Sunrise Shore - Waterfront; Private pool & hot tub!
Key West Cottages
Exterior
Key West Cottages
3.0 star property
9.8 out of 10, Exceptional, (249)
"Beautiful property. The cottages, the pool, the fire pit on the beach were all fantastic. Would recommend & will definitely return"
The price is $341
$383 total
includes taxes & fees
Jun 23 - Jun 24
Key West Cottages
Blufin Bungalows & Marina
Beach
Blufin Bungalows & Marina
3.0 star property
Blufin Bungalows & Marina
Shackeau East - Magnificent Views!
Terrace/patio
Shackeau East - Magnificent Views!
10.0 out of 10, Exceptional, (3)
"Cozy place with a wonderful view"
Shackeau East - Magnificent Views!
Cozy Little Cottage on chincoteague island va.
Property grounds
Cozy Little Cottage on chincoteague island va.
9.2 out of 10, Wonderful, (19)
"Accurate listing, small cottage but had everything we needed. We rode the Pony Express one night to dinner which was easy - we picked it up only a few steps from the house. Thanks for a great weekend."
Cozy Little Cottage on chincoteague island va.
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
9.8 out of 10, Exceptional, (260)
"We enjoyed our stay at Jesse's place! It was a short walk down to the water, had some good amenities, and when something unforeseen happened he was communicative and prepared for it and helped us out along the way. We didn't try out any of the appliances and I'm not sure this space is going to be comfortable for more than the 2 of us but since it was just 2 of us we enjoyed it very much. Will definitely plan to come back another time!"
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
Waterfront on Marsh Island!
Outdoor dining
Waterfront on Marsh Island!
9.2 out of 10, Wonderful, (9)
"We enjoyed waking every day to the water at our doorstep. The sunroom was a great place to sit. The place is a bit worn and could use some care, but it was clean and comfortable."
Waterfront on Marsh Island!
The Hideaway Cottage
Beach nearby
The Hideaway Cottage
10.0 out of 10, Exceptional, (68)
"Enjoy Don's cottage - the screened in patio was lovely to enjoy coffee and do some light office work. Kitchen had enough of everything to heat or prepare simple meals. Hot water was plentiful and pressure good in the shower. Bed was comfortable. The area is very quiet at night but during the day there is a small business next door that you do hear light people chatter/deliveries. I would say this location is like a modern cabin - just enough of everything but still feels rustic."
The Hideaway Cottage
2BR Snug Harbor Waterfront Cottage with the Most Spectacular View of lighthouse
Pool
2BR Snug Harbor Waterfront Cottage with the Most Spectacular View of lighthouse
9.6 out of 10, Exceptional, (39)
"Nice"
2BR Snug Harbor Waterfront Cottage with the Most Spectacular View of lighthouse
Only 5 min. from the Beach!
Beach
Only 5 min. from the Beach!
9.0 out of 10, Wonderful, (9)
"Easy to find and access. The dock was enjoyable with wildlife. Tha accommodation was clean and spacious for 3 adults. Nice walking paths to food and fun and shops. Definitely plan to stay again."
Only 5 min. from the Beach!
SeaLaVie!!!
1 bedroom, iron/ironing board, free WiFi, bed sheets
SeaLaVie!!!
10.0 out of 10, Exceptional, (24)
"Nice little rental. However, it needs a memory foam mattress. The old spring one has to go!!"
SeaLaVie!!!
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, (146)
"We get together once a year, 5 guys, to hang out, catch up, shoot skeet, target shoot and fish. We do this at a different location every year. This location worked out great. It was private, allowed shooting and had enough room to sleep 5. We would use this cabin again!"
Cabin at Holdens Creek on Eastern Shore of VA
5 minutes to Assateague National Seashore!
Property grounds
5 minutes to Assateague National Seashore!
9.4 out of 10, Exceptional, (6)
"Has everything you need."
5 minutes to Assateague National Seashore!
Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!
Fridge, microwave, oven, stovetop
Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!
10.0 out of 10, Exceptional, (28)
"This Island House meets all expectations for anyone looking for a beach getaway including a couple, couples, or a family. The addition of bikes, kayaks, and everything needed for a day at the beach adds to the value. The house is an easy 5 mile drive or bike ride from the beach and the neighborhood is in an imminently walkable area of town. You will have plenty of walkable options for eating and sightseeing from this house."
Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!
Small cottage for those little getaways
Exterior
Small cottage for those little getaways
10.0 out of 10, Exceptional, (90)
"Perfect for a couple or a family with young children. Kitchen was well stocked with dishes and everything you need to cook and eat in. Close to everything. Screened in porch was lovely, especially in the morning and evening. Don’t forget to bring your own linens."
Small cottage for those little getaways
Only 5 min to Assateague National Seashore!
TV, DVD player
Only 5 min to Assateague National Seashore!
9.4 out of 10, Exceptional, (6)
"Thoroughly enjoyed our stay! Very clean, close to everything yet off in a natural setting very quiet. Kitchen had everything we needed, ice machine and just really enjoyed our stay. Air/fan wouldn’t turn on and they came very quickly and fixed. Would definitely stay here again, perfect mom and daughter trip!"
Only 5 min to Assateague National Seashore!
As close as you can get to the ocean south of Chincoteague
Property grounds
As close as you can get to the ocean south of Chincoteague
10.0 out of 10, Exceptional, (124)
"We really enjoyed our stay at this little slice of paradise! The views from the screened in porch or the back decks we’re just beautiful. It truly is a birders paradise with bald eagles, purple Martins, Barnes swallows, mockingbird, willets And an abundance of shorebirds. The house was very well stocked including hand soap, dish soap, paper towels, toilet paper, coffee filter and much more. I did bring my own kayaks but really didn’t need to because there were nice ones there for guest use. The...
The price is $300
$502 total
includes taxes & fees
Jun 16 - Jun 17
As close as you can get to the ocean south of Chincoteague
Don't see what you're looking for?
See all available 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.

Other types of properties in Deep Hole you may be interested in

Quaint Cottages Near Everything on Beach Road
Exterior
Quaint Cottages Near Everything on Beach Road
9.6 out of 10, Exceptional, (25)
"Quiet neighborhood. Conveniently close to the refuge and restaurants."
Quaint Cottages Near Everything on Beach Road
Oyster Bay Hideaway on Chincoteague Island!
Fridge, microwave, oven, stovetop
Oyster Bay Hideaway on Chincoteague Island!
10.0 out of 10, Exceptional, (3)
"Clean and convenient Highly recommend"
Oyster Bay Hideaway on Chincoteague Island!
Jay’s Retreat: EV Charger-Kayaks-Bikes-Fire Pit-Private Dock-Pets Ok-Crabbing
Property grounds
Jay’s Retreat: EV Charger-Kayaks-Bikes-Fire Pit-Private Dock-Pets Ok-Crabbing
10.0 out of 10, Exceptional, (189)
"The hosts were very communicative. We made good use of the propane grill and ran out. The host was there with a new tank within 5 minutes. The kitchen was very well equipped with everything needed to cook and a good supply of a variety of spices. The hot water on demand was welcome for warm showers on chilly nights."
Jay’s Retreat: EV Charger-Kayaks-Bikes-Fire Pit-Private Dock-Pets Ok-Crabbing
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.

Everything you need to know about Deep Hole vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Deep Hole vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Deep Hole vacation 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 low season months. For more hustle and bustle, you may prefer to visit Deep Hole in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $300 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Deep Hole rentals

At Expedia, we put the best Deep Hole vacation 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 vacation.

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 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: You might like this vacation home rental near Deep Hole. It has 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 Oyster Bay Hideaway on Chincoteague Island!.

How many vacation rentals are there in Deep Hole?

Expedia has 79 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 Chincoteague National Wildlife Refuge and Assateague Lighthouse.

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.

Recent reviews of Deep Hole properties
Expedia verified reviews

Refuge Inn

Refuge Inn

5/5 Excellent
"The decor has a warm feel and it’s a unique hotel—obviously not a cookie-cutter National chain"
A verified traveler stayed at Refuge Inn
Posted 1 day ago
Refuge Inn