Holiday Rentals in Deep Hole

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Holiday Rentals in Deep Hole

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
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!
Property grounds
★Jay’s Waterfront Retreat: Private Dock-Fire-pit-Kayaks & Bikes Inc.-Beach★
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 Waterfront Retreat: Private Dock-Fire-pit-Kayaks & Bikes Inc.-Beach★
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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!
Exterior
Key West Cottages
3.0 star property
9.8 out of 10, Exceptional, (234)
"Charming! Key West Cottages are so cute! The cottages are new and well built, with all the amenities you need for your stay. Everything about this place is quality. There is even a beach to watch the sunset. We loved our time there and would highly recommend staying at the cottages. "
The price is €185
includes taxes & fees
4 Jun - 5 Jun
Key West Cottages
Beach
Blufin Bungalows & Marina
3.0 star property
Blufin Bungalows & Marina
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
9.8 out of 10, Exceptional, (258)
"We loved the cottage. Perfect location to everything on the island. Was within walking distance to the seafood festival and shops. The screened porch was a nice place to enjoy our morning coffee. The cottage had everything we needed. The bed was super comfy. We highly recommend staying there. We are considering a summer visit and hope the cottage is available if we do."
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
Property grounds
Cozy Little Cottage on chincoteague island va.
9.6 out of 10, Exceptional, (17)
"This was our second time staying here, with our first being during the summer. The cottage is very clean and overall quite pleasant with a location perfect for bicycling into town and to the beach. However, this cottage really needs heat if it is to be rented during the cooler months. The owner did provide a portable heater at our request, which did warm the place, but was very noisy. Would stay again but only in the warmer weather. "
Cozy Little Cottage on chincoteague island va.
Terrace/patio
Shackeau East - Magnificent Views!
10.0 out of 10, Exceptional, (2)
"Cozy place with a wonderful view"
Shackeau East - Magnificent Views!
Outdoor dining
Waterfront on Marsh Island!
9.2 out of 10, Wonderful, (7)
"Such a great island to visit. The Bay view was perfect. Got to see the sunset on our first night. Easy trip onto the Island for dinner at Rope Walk and Bills Steak & Seafood. Both were excellent. The bed was not very comfortable and the AC was not the greatest. Overall a great place to stay for a long weekend."
Waterfront on Marsh Island!
Pool
2BR Snug Harbor Waterfront Cottage with the Most Spectacular View of lighthouse
9.6 out of 10, Exceptional, (38)
"Snug Harbor is simply amazing, and is truly a home away from home. The location is on the water with amazing views of the lighthouse and the poines. There are tiki huts, lawn chairs, etc. for you to enjoy. Basia and Captain John can take you on kayak and boat tours. I highly recommend taking a guided tour as you learn so much history. Our hosts were so committed to us having a great time and went the extra mile so we could see the poines every chance possible. The cottages are comfortable...
2BR Snug Harbor Waterfront Cottage with the Most Spectacular View of lighthouse
Fridge, microwave, oven, stovetop
Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!
10.0 out of 10, Exceptional, (27)
"The house is a character in itself, loved the stay."
The price is €327
includes taxes & fees
27 May - 28 May
Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!
Interior
Cabin at Holdens Creek on Eastern Shore of VA
9.6 out of 10, Exceptional, (145)
"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
Beach
Only 5 min. from the Beach!
8.6 out of 10, Excellent, (7)
"The property was fine, however, both doors did not close tightly. I could see daylight through the bottom corner of both doors. The property was full of flies, I kill them every evening and there were 3-6 when I came back the next evening. They were coming in from somewhere, the doors? The property was very clean but I gave 4 stars because the rug in front of the sink was pretty gross. The towel rack was barely attached to the wall."
The price is €176
includes taxes & fees
28 May - 29 May
Only 5 min. from the Beach!
1 bedroom, iron/ironing board, free WiFi, bed sheets
SeaLaVie!!!
10.0 out of 10, Exceptional, (22)
"Was very quite and cute little cottage. Very nicely decorated. Creative in making use of the lack of floor space. Made it work! We would stay again."
SeaLaVie!!!
Exterior
Small cottage for those little getaways
10.0 out of 10, Exceptional, (89)
"Enjoyed our time great bang for the buck."
Small cottage for those little getaways
Property grounds
As close as you can get to the ocean south of Chincoteague
10.0 out of 10, Exceptional, (122)
"The house was perfect for our family’s long weekend stay in April 2024. The location is splendid for its views, water accessibility and peace and quiet. We kayaked to the barrier island (approx.15 min) and found many pristine whelk sea shells. We thoroughly enjoyed crabbing and fishing in the creek as well bird watching. The homeowners really have provided just about everything you could ask for as far as amenities and supplies. Additionally they were very helpful and informative when we had...
The price is €595
includes taxes & fees
16 Jun - 17 Jun
As close as you can get to the ocean south of Chincoteague
Fridge, microwave, oven, stovetop
The Brass Crab - Check in/out any day!
10.0 out of 10, Exceptional, (133)
"Overall the space was great. With the money and fees paid, the beds should be made upon arrival. Also more towels for the kitchen area would be helpful. It was a lovely stay"
The Brass Crab - Check in/out any day!
Property grounds
Tranquil Shores - Relaxation With a Water View!
9.8 out of 10, Exceptional, (116)
"love the house, the location and it is the perfect size. Deck and screened porch are perfect too. Nice neighborhood also. Very clean and comfy. Thank you for allowing well behaved dogs too :)"
Tranquil Shores - Relaxation With a Water View!
Sauna
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
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

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
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!
Property grounds
★Jay’s Waterfront Retreat: Private Dock-Fire-pit-Kayaks & Bikes Inc.-Beach★
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 Waterfront Retreat: Private Dock-Fire-pit-Kayaks & Bikes Inc.-Beach★
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 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, apart-hotels, 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 favorite 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 depends 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 €176 per night. Entering your travel dates in the search wizard you might find 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.

How many holiday rentals are there in Deep Hole?

Expedia has 79 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 Chincoteague National Wildlife Refuge and Assateague Lighthouse.

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.

Recent reviews of Deep Hole properties
Expedia verified reviews

Key West Cottages

Key West Cottages

5/5 Excellent
Best Place on Chincoteague!!!
"Charming! Key West Cottages are so cute! The cottages are new and well built, with all the amenities you need for your stay. Everything about this place is quality. There is even a beach to watch the sunset. We loved our time there and would highly recommend staying at the cottages. "
A verified traveller stayed at Key West Cottages
Posted 2 days ago
Key West Cottages