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Top 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, (172)
"Beautiful cabin situated at the back of a farm, very peaceful. Very spacious and inviting. Only a half hour to Chincoteague and an hour to Ocean City. Nice porch with a swing and 2 chairs to sit out in the morning with a cup of coffee (coffee maker provided). We loved having a pool table for our evening entertainment. Only thing we didn't like was the very tiny kitchen, absolutely no counter space at all :( "
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 £143
includes taxes & fees
31 Aug - 1 Sept
Cottage near the Bay

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

9.6 out of 10, Exceptional, (22)
"Perfect base to go out and explore and fish the Chesapeake. "
Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly

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

10.0 out of 10, Exceptional, (15)
"Hubs and I were looking for a relaxing getaway and boy did we find it. This cottage was perfect. "
The price is £200
includes taxes & fees
1 Sept - 2 Sept
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock

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

9.2 out of 10, Wonderful, (156)
"Beautiful spot. Location location location! Can’t wait to go back"
Remote Secluded Waterfront Estate OPEN for Chincoteague Pony Week. Only 37 Mi

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

Beautiful Bayfront with Sanctuary Private Beach

9.2 out of 10, Wonderful, (21)
"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

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

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

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.

Charming Cottage - Ultimate Relaxation Destination

10.0 out of 10, Exceptional, (119)
"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

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

10.0 out of 10, Exceptional, (57)
"What an amazing home and property!! We just returned from a great stay and cant say enough about this gorgeous house! From the beautiful decor, well stocked kitchen, barn full of toys, there isnt a thing that was overlooked by the owners! Cant wait to return!"
Waterfront Estate - Amazing Views And Sunsets - Pet Friendly - New rate for 2025

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

2.0 star property
10.0 out of 10, Exceptional, (3)
"Had an amazing time here very piecefull and beautiful "
Par-Lon - Private Raised Waterfront Home on the Pocomoke River

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

10.0 out of 10, Exceptional, (32)
"Beautiful panorama!"
The Porter's Barn - fancy little waterfront home with deep-water boat dock and firepit

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

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

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!

Inviting Waterfront Cottage on Cedar Creek

10.0 out of 10, Exceptional, (37)
"We had a wonderful stay. We enjoyed the kayaks and the firepit as well as a few local restaurants. The house was clean and the host was very responsive. "
Inviting Waterfront Cottage on Cedar Creek

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

8.8 out of 10, Excellent, (28)
"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.

Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

10.0 out of 10, Exceptional, (26)
"Wonderful stay and beautiful accomodations"
The price is £241
includes taxes & fees
21 Aug - 22 Aug
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
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

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.