Deep Hole Vacation Rentals

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Vacation Rentals in Deep Hole

Quaint Cottages Near Everything on Beach Road
9.6 out of 10, Exceptional, 25 reviews
"Quiet neighborhood. Conveniently close to the refuge and restaurants."
Quaint Cottages Near Everything on Beach Road
Oyster Bay Hideaway on Chincoteague Island!
10.0 out of 10, Exceptional, 3 reviews
"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
10.0 out of 10, Exceptional, 189 reviews
"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!
8.8 out of 10, Excellent, 31 reviews
"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
3.0 star property
9.8 out of 10, Exceptional, 238 reviews
"Fantastic in every way, if the owners are reading, sorry we forgot to take out trash, we didn't remember until half way home! "
The price is CA $282
CA $317 total
includes taxes & fees
Jun 4 - Jun 5
Key West Cottages
Blufin Bungalows & Marina
3.0 star property
Blufin Bungalows & Marina
Shackeau East - Magnificent Views!
10.0 out of 10, Exceptional, 2 reviews
"Cozy place with a wonderful view"
Shackeau East - Magnificent Views!
Cozy Little Cottage on chincoteague island va.
9.0 out of 10, Wonderful, 18 reviews
"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.
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
9.8 out of 10, Exceptional, 258 reviews
"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!
Waterfront on Marsh Island!
9.2 out of 10, Wonderful, 7 reviews
"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!
2BR Snug Harbor Waterfront Cottage with the Most Spectacular View of lighthouse
9.6 out of 10, Exceptional, 38 reviews
"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
SeaLaVie!!!
10.0 out of 10, Exceptional, 23 reviews
"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!!!
Cabin at Holdens Creek on Eastern Shore of VA
9.6 out of 10, Exceptional, 145 reviews
"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
The Hideaway Cottage
10.0 out of 10, Exceptional, 68 reviews
"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
Only 5 min. from the Beach!
8.6 out of 10, Excellent, 7 reviews
"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."
Only 5 min. from the Beach!
Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!
10.0 out of 10, Exceptional, 27 reviews
"The house is a character in itself, loved the stay."
The price is CA $247
CA $508 total
includes taxes & fees
Jun 3 - Jun 4
Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!
As close as you can get to the ocean south of Chincoteague
10.0 out of 10, Exceptional, 123 reviews
"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 CA $412
CA $689 total
includes taxes & fees
Jun 16 - Jun 17
As close as you can get to the ocean south of Chincoteague
Small cottage for those little getaways
10.0 out of 10, Exceptional, 89 reviews
"Enjoyed our time great bang for the buck."
Small cottage for those little getaways
5 minutes to Assateague National Seashore!
9.2 out of 10, Wonderful, 5 reviews
"Our stay this time was in a different room than last December but just as good! The view was great- location was very convenient. Room clean and orderly. Everything as described. It is perfect for my husband and I, has everything we need. The toaster didn’t work and they replaced it immediately. We stayed two extra days! Loved it! Will definitely book again! Thank you!"
5 minutes to Assateague National Seashore!
Tranquil Shores - Relaxation With a Water View!
9.8 out of 10, Exceptional, 116 reviews
"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!
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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
9.6 out of 10, Exceptional, 25 reviews
"Quiet neighborhood. Conveniently close to the refuge and restaurants."
Quaint Cottages Near Everything on Beach Road
Oyster Bay Hideaway on Chincoteague Island!
10.0 out of 10, Exceptional, 3 reviews
"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
10.0 out of 10, Exceptional, 189 reviews
"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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Deep Hole. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.

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