Deep Creek Holiday Rentals

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Holiday Rentals in Deep Creek

Cabin at Holdens Creek on Eastern Shore of VA

9.6 out of 10, Exceptional, (158)
"An amazing experience with amazing people. We made this annual visit and every year it gets better and better. We will definitely be coming back. Thank you so much to the hosts for having us and best wishes."
Cabin at Holdens Creek on Eastern Shore of VA

Creek House - Waterfront Oasis on Holden's Creek

9.8 out of 10, Exceptional, (6)
"The location, accommodations and the quality of the amenities were stellar. The best vacation we have spent as a family! The whole experience was best in class!"
Creek House - Waterfront Oasis on Holden's Creek

As close as you can get to the ocean south of Chincoteague

10.0 out of 10, Exceptional, (134)
"We had a wonderful time at this beautifully appointed home. Everything was just as advertised. Six kayaks, gas grill, beautiful view and great kitchen/dining areas. Our hostess was wonderful to us. "
As close as you can get to the ocean south of Chincoteague

Cottage near the Bay

8.6 out of 10, Excellent, (27)
"Attended a family wedding in the area. Perfect distance "
The price is AU$310
includes taxes & fees
25 Nov - 26 Nov
Cottage near the Bay

Waterfront 3 bedroom condo. Fall and oysters are here!

10.0 out of 10, Exceptional, (36)
"We soent three nights. Sunsets were amazing. Slept well and the kitchen was easy to cook in."
Waterfront 3 bedroom condo. Fall and oysters are here!

Secluded/Remote/Waterfront Estate BOOK NOW OPENINGS GOING QUICK

9.4 out of 10, Exceptional, (151)
"This was exactly what I was looking for. The Property is very private and the yard surrounding the house was huge. I found it comfortable and cozy. Randy was very accommodating and asked that you respected his property and clean up after yourself and your pets which is to be expected were I come from, a small ask. He had plenty to offer. The private dock and water access was perfect and being able to us his canoes and kayaks was a very nice extra. One of my favorite things was the very large...
Secluded/Remote/Waterfront Estate BOOK NOW OPENINGS GOING QUICK

ESVA Down by the Sea & Pet Friendly

10.0 out of 10, Exceptional, (2)
"Very nice place. Located in a great spot for our needs. First thing we noticed was how clean it was. I will definitely book this again on our next trip to ESVA!"
ESVA Down by the Sea & Pet Friendly

Calling all hunters, almost 33 more acres across the street used for hunting.

9.2 out of 10, Wonderful, (27)
"This house and property are beautiful. It is very secluded and right on the water. The house was spotless when I arrived and has everything you need or want. The pool is huge. I had an awesome stay and I cannot wait until I go back in August!"
Calling all hunters, almost 33 more acres across the street used for hunting.

Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock

10.0 out of 10, Exceptional, (5)
"Very nice property, we made good use of the dock and were able to launch my 18.5 ft boat from the concrete ramp. Fishing, crabbing, boating were good (though crabs a bit on small side) the cottage was clean, well organized and neat. Everything was really nice and Genevieve was extremely responsive and pleasant to deal with."
The price is AU$457
includes taxes & fees
25 Nov - 26 Nov
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock

Beautiful Bayfront with Sanctuary Private Beach

9.0 out of 10, Wonderful, (17)
"The property is beautiful and it was so nice to be so close to the water. Sunset view and fire pit out back were fun bonuses. Everything went smoothly and as expected. We enjoyed our stay, thank you!"
Beautiful Bayfront with Sanctuary Private Beach

Awesome private off grid cabin with creek view.

9.6 out of 10, Exceptional, (13)
"Super relaxing. Chill. Best of times. "
Awesome private off grid cabin with creek view.

Charming Cottage - Ultimate Relaxation Destination

10.0 out of 10, Exceptional, (113)
"This cottage was perfectly appointed and was located less than a 10 minute walk into downtown Onancock. The cottage was spacious inside and the property had a nice fire pit area by a little creek. Doris was easily accessible and we would rent here again. "
Charming Cottage - Ultimate Relaxation Destination

Bayfront Retreat w/ Game Room + Outdoor Pool!

9.8 out of 10, Exceptional, (32)
"Our second time staying at the house. We absolutely love the property and all its surrounding wildlife. Enjoyed spending time hiking, fishing, crabbing, and watching eagles flying over the water. The house is clean and well stocked, and the game room is a great place to spend time in the evenings or rainy days. The hosts are attentive and helpful. Looking forward to visiting again!"
Bayfront Retreat w/ Game Room + Outdoor Pool!

Come, sit back and relax at the "Catch of the Bay"

10.0 out of 10, Exceptional, (5)
"This was a great place to stay and I highly recommend it to anyone. We were really impressed with all the "extras" that were included. We didn't need to go out any buy anything unexpected."
Come, sit back and relax at the "Catch of the Bay"

Secluded Seaside Village Retreat in Fishing Town

9.6 out of 10, Exceptional, (10)
"Great house with a lot of space for relaxing. Nice quiet neighborhood with kind neighbors and close to many Eastern Shore attractions. Absolutely loved the location!"
Secluded Seaside Village Retreat in Fishing Town

Charming Painter Home w/ Chesapeake Bay Views

8.2 out of 10, Very good, (43)
"Stayed here to go fishing worked out great"
Charming Painter Home w/ Chesapeake Bay Views

Timeless Elegance with Modern Luxury: Historic 6-Bedroom Home-Newly Renovated!

10.0 out of 10, Exceptional, (1)
"This location worked well for our large group which comprised of 3 generations. The historic style of the home works well with the renovations which include strong WiFi, new appliances and plenty of high-tech flat screen televisions. The area was very quiet and near plenty of shopping locations. This was the perfect home for family time and bonding. The host was responsive to our questions and requests. We definitely plan to stay here again! Thanks, Steve! Your home was perfect for our...
The price is AU$1,222
includes taxes & fees
5 Dec - 6 Dec
Timeless Elegance with Modern Luxury: Historic 6-Bedroom Home-Newly Renovated!

Blue Heron - A Breathtaking Eastern Shore Vacation Experience!

9.8 out of 10, Exceptional, (29)
"Everything was clean! Beautiful house and property! Perfect for our family!!"
Blue Heron - A Breathtaking Eastern Shore Vacation Experience!

Home on Chesapeake Bay: Large Yard, Fire Pit

9.0 out of 10, Wonderful, (6)
"Very comfortable, clean and cute place with a peaceful back yard where we watched wildlife, and the neighbors adorable flock of chickens! ! Great location close to town."
Home on Chesapeake Bay: Large Yard, Fire Pit

BEAUTIFUL REMODELED "COTTAGE BY THE BAY" in CRISFIELD! WE STRIVE TO BE THE BEST!

10.0 out of 10, Exceptional, (5)
"The cottage is absolutely perfect! The decor is perfect, the amenities were thoughtful, and the house was immaculate! It was convenient to everything in town. The hosts were wonderful, friendly, knowledgeable and responded quickly to messages. We loved our stay and would definitely visit again!"
BEAUTIFUL REMODELED "COTTAGE BY THE BAY" in CRISFIELD! WE STRIVE TO BE THE BEST!
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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Other types of properties in Deep Creek you may be interested in

Hampton Inn & Suites Exmore - Eastern Shore

2.5 star property
8.4 out of 10, Very good, (922)
"I loved it"
The price is AU$125
includes taxes & fees
6 Dec - 7 Dec
Hampton Inn & Suites Exmore - Eastern Shore

Holiday Inn Express and Suites Exmore, Eastern Shore, an IHG Hotel

2.5 star property
8.2 out of 10, Very good, (688)
"We stop here every year on our way through to the Outer Banks. Clean, comfortable, friendly & reasonably priced. Perfect for a quick overnight stay. Oh, breakfast is a nice plus too!"
The price is AU$141
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn Express and Suites Exmore, Eastern Shore, an IHG Hotel

Onley Inn

2.0 star property
6.6 out of 10, (694)
"Outdated but clean "
The price is AU$128
includes taxes & fees
25 Nov - 26 Nov
Onley Inn
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find holiday rentals in Deep Creek?

Yes, there are holiday rentals close to the most popular sights in Deep Creek, 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 Creek has to offer?

Creek House - Waterfront Oasis on Holden's Creek: This holiday home rental outside of Deep Creek is located on a river, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

What can I see and do in Deep Creek?

While exploring the area, visit family-friendly sights like SouthEast Expeditions, or get outside and enjoy nature at Parramore Beach. Hang Glide Virginia and North Street Market are a couple of places you'll find in the wider area.

What are holiday rentals like in Deep Creek?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Deep Creek. Holiday rentals offer amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for a small group gathering.