Deep Creek Holiday Rentals

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Holiday Rentals in Deep Creek

Our top choices for Deep Creek holiday rentals

Cabin at Holdens Creek on Eastern Shore of VA

9.6 out of 10, Exceptional, (178)
"I like the fact that we were away from the hustle and bustle. The beaches are near by. And it was an overall great experience. Especially if you like secluded areas "
Cabin at Holdens Creek on Eastern Shore of VA

Cottage near the Bay

9.0 out of 10, Wonderful, (43)
"great, peaceful "
The price is AU$292
includes taxes & fees
7 Sept - 8 Sept
Cottage near the Bay

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

9.0 out of 10, Wonderful, (2)
"very clean and neat, quiet. just what i needed"
Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Remote Secluded Waterfront Estate OPEN for Chincoteague Pony Week. Only 37 Mi

9.2 out of 10, Wonderful, (157)
"We had an absolute blast over Memorial Day weekend! The house was the perfect getaway — peaceful, relaxing, and full of little adventures. The pier was a highlight for us. We caught 3 stingrays, 2 eels, fish, crab, and even oysters — such a fun variety that kept us on our toes!It was also such a treat to bring our dogs along and include our fur family in the fun. We enjoyed dinner every night in the screened-in patio and sipped coffee each morning on the upstairs deck — just the kind of relaxing...
Remote Secluded Waterfront Estate OPEN for Chincoteague Pony Week. Only 37 Mi

Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly

9.6 out of 10, Exceptional, (22)
"We enjoyed our stay - everything was provided and comfortable. We definitely recommend the location - could go kayaking, biking, and enjoy the back porch every day."
Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly

Beautiful, Waterfront, Luxury

10.0 out of 10, Exceptional, (4)
"Great place for a weekend away - house was beautiful and hosts were always quick to answer"
Beautiful, Waterfront, Luxury

Charming Cottage - Ultimate Relaxation Destination

10.0 out of 10, Exceptional, (123)
"I had stayed at this property in the past and was really glad to get to stay again. It is clean, quiet, and close to the town center of Onancock. Really looking forward to returning!"
Charming Cottage - Ultimate Relaxation Destination

Beautiful Bayfront with Sanctuary Private Beach

9.2 out of 10, Wonderful, (22)
"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

The Porter's Barn - fancy little waterfront home with deep-water boat dock and firepit

10.0 out of 10, Exceptional, (33)
"Beautiful panorama!"
The Porter's Barn - fancy little waterfront home with deep-water boat dock and firepit

Walk to Main Street: Family-Friendly Crisfield Gem

10.0 out of 10, Exceptional, (2)
"Beautiful property"
Walk to Main Street: Family-Friendly Crisfield Gem

A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore

10.0 out of 10, Exceptional, (2)
"Nice little cottage for short stay and great location "
The price is AU$292
includes taxes & fees
9 Sept - 10 Sept
A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore

Par-Lon - Private Raised Waterfront Home on the Pocomoke River

2.0 star property
10.0 out of 10, Exceptional, (4)
"The house was beautiful and our stay was great. Looking forward to future visits. "
Par-Lon - Private Raised Waterfront Home on the Pocomoke River

Creek House - Waterfront Oasis on Holden's Creek

9.8 out of 10, Exceptional, (11)
"This property was lovely in every respect—its site on Holdens Creek, its living and sleeping spaces, and its proximity to Assateague where we went for a day. We highly recommend it for a family group. "
Creek House - Waterfront Oasis on Holden's Creek

Awesome private off grid cabin with creek view.

9.8 out of 10, Exceptional, (16)
"Beautiful slice of heaven on the creek. Lots of wildlife and close enough to downtown that you can have a nice night out or just light a fire and enjoy nature."
Awesome private off grid cabin with creek view.

Walk to Main St: Condo w/ Pool Access in Crisfield

8.6 out of 10, Excellent, (4)
"My stay at this Condo was great. Loved the view and had everything we needed. Very nice place to stay if you visit the Eastern Shore. Beds were very comfortable and really enjoyed the sunsets here. They also had a pool but I didn't use it we were busy each day. Thanks for the great week at your Condo highly recommend to stay here. I give it 5 stars"
Walk to Main St: Condo w/ Pool Access in Crisfield

Entire 4-bedroom 2-bath Cabin with AC, Recreational rooms, WiFi in Crisfield, MD

8.6 out of 10, Excellent, (4)
"Our stay was amazing. The cabin was exactly as described. 9 family member stayed at the cabin comfortably. The view of the lake was breathtaking, the property was quiet and inviting with plenty of space for celebrating. We came to attend the Crab and Cruise experience which was a short drive from tge property. The surrounding city was quaint and friendly."
Entire 4-bedroom 2-bath Cabin with AC, Recreational rooms, WiFi in Crisfield, MD

Chesapeake Bay Retreat Private Dock + Beach

10.0 out of 10, Exceptional, (1)
"Came to the eastern shore for a wedding-could not have found a better property or owner! Great communication, property was better than advertised—we will be back!! Thanks so much to Genevieve for being so attentive and helpful!!!"
Chesapeake Bay Retreat Private Dock + Beach

Family Friendly Waterfront Escape w/pier, gameroom, and fire pit!

9.4 out of 10, Exceptional, (6)
"The property was perfect for a very relaxing weekend. The house was exactly what we needed for our little group."
Family Friendly Waterfront Escape w/pier, gameroom, and fire pit!

Waterfront Estate - Amazing Views And Sunsets - Pet Friendly - New rate for 2025

10.0 out of 10, Exceptional, (57)
"First, the house is clean, well-stocked with the comforts of home, and architecturally stunning in a classic/traditional way. The sunsets are amazing. The breezes off the bay are refreshing. The whole property has a sense of peace. As a young man, I grew up fishing the many lakes, bays and marshlands of Louisiana …. also I worked and played on my grandfather’s farm in Virginia. This plays combines the two, magnificently. My wife, our two young boys, and the dog were at ease in this wonderful...
Waterfront Estate - Amazing Views And Sunsets - Pet Friendly - New rate for 2025

Harbor Master-Waterfront 3 bedroom home with endless pool pickleball fenced yard

10.0 out of 10, Exceptional, (1)
"Peaceful, relaxing place with wonderful waterfront views. House is spacious and well-stocked, with a large fenced yard. We enjoyed catching fish and blue crabs right from the dock and kayaking on the river. Highly recommend. "
Harbor Master-Waterfront 3 bedroom home with endless pool pickleball fenced yard
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 Creek Hotel Reviews

Find out more about Deep Creek

Find out more about Deep Creek

Everything you need to know about Deep Creek 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 Creek holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Creek holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Deep Creek holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Deep Creek. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Deep Creek 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 Creek holiday rentals we have selected for you start as low as AU$292 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Deep Creek rentals

At Expedia, we put the best Deep Creek 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 Creek 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 Creek 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 Creek. 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 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?

Cottage near the Bay: This holiday home rental outside of Deep Creek is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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 Tangier Island 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.