Crisfield Holiday Rentals

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Holiday Rentals in Crisfield

Cottage near the Bay

9.0 out of 10, Wonderful, (36)
"We enjoyed our stay. The host was very responsive to our needs and I appreciate her flexible schedule"
The price is AU$288
includes taxes & fees
14 July - 15 July
Cottage near the Bay

Walk to Main Street: Family-Friendly Crisfield Gem

10.0 out of 10, Exceptional, (1)
"Beautiful property"
Walk to Main Street: Family-Friendly Crisfield Gem

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

10.0 out of 10, Exceptional, (6)
"It was very good, very clean and cozy. I would recommend the place for sure."
Come, sit back and relax at the "Catch of the Bay"

Waterfront Chesapeake Bay Condo w/ Boat Slip!

10.0 out of 10, Exceptional, (11)
"Gorgeous views, clean and well appointed condo, peaceful and relaxing. Great stay!"
Waterfront Chesapeake Bay Condo w/ Boat Slip!

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

8.0 out of 10, Very good, (3)
"Great location. Needed to be cleaned a bit better. Lots of dust. Fridge and the utensils needed to be cleaned….. One small tv in the living room was not enough. Needed a tv in the bedroom. Good overall. "
Walk to Main St: Condo w/ Pool Access in Crisfield

Cabin at Holdens Creek on Eastern Shore of VA

9.6 out of 10, Exceptional, (168)
"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

Serenity Cottage: Central to state parks, historic towns, MD & VA beaches

10.0 out of 10, Exceptional, (7)
"Great location close to main road but quiet and removed from the busy tourist area of the island. Clean property with all the necessities. Quick and easy communication with property manager.."
Serenity Cottage: Central to state parks, historic towns, MD & VA beaches

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

10.0 out of 10, Exceptional, (11)
"The place is amazing. The pictures on the site do not do the property justice as it is absolutely amazing. Can’t wait to stay there again."
The price is AU$471
includes taxes & fees
17 July - 18 July
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock

Beautiful Bayfront with Sanctuary Private Beach

9.2 out of 10, Wonderful, (19)
"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

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

9.4 out of 10, Exceptional, (19)
"Perfect base to go out and explore and fish the Chesapeake. "
Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly

Waterfront Historic Gem w/ Kayaks & Fire Pit

8.0 out of 10, Very good, (2)
"Great house. Clean. Had everything we needed."
Waterfront Historic Gem w/ Kayaks & Fire Pit

Awesome private off grid cabin with creek view.

9.6 out of 10, Exceptional, (14)
"Exactly what we were looking for! Indoor stove ready to go upon our arrival. Very cold weekend but the stove works really well to keep it warm inside. Gas grill outside. Everything you need to do basic cooking inside. Would absolutely stay again!"
Awesome private off grid cabin with creek view.

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

10.0 out of 10, Exceptional, (32)
"I have to admit, I didn’t want to leave - so I stayed another night.The Barn itself is just absolute perfection…. Not to mention the beyond beautiful setting!I haven’t been that relaxed in years."
The Porter's Barn - fancy little waterfront home with deep-water boat dock and firepit

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Pet-Friendly Smith Island Cottage w/ Golf Cart!

10.0 out of 10, Exceptional, (17)
"The island is a beautiful and peaceful. Everyone there is so friendly and helpful. The cottage was a very clean and comfortable place to stay. We had 3 adults and 2 huskies and the home was very spacious. It is close to the docks, restaurant, and grocery store. We enjoyed our stay. If you’re looking for a peaceful and relaxing getaway this is the place to go! "
Pet-Friendly Smith Island Cottage w/ Golf Cart!

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (38)
"This property was perfect for a family of 4. It was very clean, the kitchen was well stocked and the neighbors were amazing and helpful. Visit the arcade by the marina right before sunset!"
Historic home on Smith Island w/ dock!

Waterfront Maryland Retreat w/ Dock & Bay View!

9.8 out of 10, Exceptional, (8)
"Beautiful sunset views and well accommodating house. "
Waterfront Maryland Retreat w/ Dock & Bay View!

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

10.0 out of 10, Exceptional, (56)
"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

IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

10.0 out of 10, Exceptional, (16)
"Took my grandson for a weekend trip to Smith Island to celebrate his HS graduation. My daughter, also, accompanied us, since I am a 90 year old "Grammy", and need some assistance. Our cottage was clean, comfortable and had all of our needs. The host, Kim, was extremely attentive, and made our dinner the night we arrived so we could just relax. I would highly recommend Idle Hour as the place to stay on Smith Island. Pat Reynolds, Ellicott City, MD"
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

9.8 out of 10, Exceptional, (8)
"Smith island is lovely! This house was perfectly located and furnished and the owner super helpful."
The price is AU$426
includes taxes & fees
14 July - 15 July
Get away to relax on Smith Island in the Chesapeake Bay with golf cart included
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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Frequently asked questions

Are there holiday rentals in Crisfield?

Yes, there are holiday rentals close to the most popular sights in Crisfield, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Crisfield has a good selection of seafood restaurants. Make sure you have time to check out the waterfront while you're in the area.

What are some of the best holiday rentals that Crisfield has to offer?

Cottage near the Bay: This highly rated holiday home rental in Crisfield 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. Our travellers also rate Walk to Main Street: Family-Friendly Crisfield Gem as a favourite home for rent in Crisfield.

How many holiday rentals will I find in Crisfield?

Choose from 4 Expedia holiday rentals in Crisfield for a memorable holiday.

What’s there to see and do in Crisfield?

Wellington Beach and Park and Big Island are a couple of scenic spots to enjoy the outdoors, whereas J. Millard Tawes Museum is one of the cultural attractions. Somers Cove Marina and Crisfield City Dock are other places to visit while you're in town.

What’s a holiday rental in Crisfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Crisfield. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for family gatherings.