Crisfield Holiday Rentals from €166: Search Short-Term Rentals

Q: 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.

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Holiday Rentals in Crisfield

"great, peaceful "

includes taxes & fees

24 Aug - 25 Aug

"Beautiful property"

"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"

"It was very good, very clean and cozy. I would recommend the place for sure."

"Gorgeous views, clean and well appointed condo, peaceful and relaxing. Great stay!"

"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 :( "

"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!"

"Perfect base to go out and explore and fish the Chesapeake. "

"Hubs and I were looking for a relaxing getaway and boy did we find it. This cottage was perfect. "

includes taxes & fees

1 Sept - 2 Sept

"very clean and neat, quiet. just what i needed"

"Great place for a weekend away - house was beautiful and hosts were always quick to answer"

"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!"

"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! "

"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"

"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."

"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!"

"The house is absolutely beautiful and the view is spectacular ! If by chance you forget to bring something with you dont worry they have it all right down to the lotion. The neighbors are great too ! Loved our stay."

"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!"

"Smith island is lovely! This house was perfectly located and furnished and the owner super helpful."

includes taxes & fees

20 Aug - 21 Aug

"Had an amazing time here very piecefull and beautiful "

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Top Crisfield Hotel Reviews

Econo Lodge Pocomoke City Hwy 13

10/10 Excellent

"Rooms are comfortable and clean. It’s decent place to stay if your passing through Pocomoke and need to rest for the night. "

The Charlotte Hotel & Restaurant

10/10 Excellent

"This is a quaint b&b-style hotel in a charming town. The room was comfortable and sufficient. There's no fridge or kettle in the room, but there's a Keurig downstairs and baked goods from the bakery next door. There was a pub across the street, and we thought the festivities might keep us up, but everyone turned in early and it wasn't an issue. Overall, a very pleasant stay."

Find out more about Crisfield

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

Crisfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Crisfield. 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Crisfield 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 Crisfield holiday rentals we have selected for you start as low as €166 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Crisfield rentals

At Expedia, we put the best Crisfield 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 Crisfield 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 Crisfield 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 Crisfield. 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

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 Jersey 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.

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Holiday Rentals in Crisfield

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Holiday Rentals in Crisfield

Cottage near the Bay

Walk to Main Street: Family-Friendly Crisfield Gem

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

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

Waterfront Chesapeake Bay Condo w/ Boat Slip!

Cabin at Holdens Creek on Eastern Shore of VA

Historic home on Smith Island w/ dock!

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

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

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Beautiful, Waterfront, Luxury

Beautiful Bayfront with Sanctuary Private Beach

Pet-Friendly Smith Island Cottage w/ Golf Cart!

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

Awesome private off grid cabin with creek view.

Charming Cottage - Ultimate Relaxation Destination

Waterfront Maryland Retreat w/ Dock & Bay View!

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

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

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

Top Crisfield Hotel Reviews

Econo Lodge Pocomoke City Hwy 13

Best Western Plus Pocomoke City

The Charlotte Hotel & Restaurant

Regal Inn

The Whitehaven Hotel

Studio 6 Suites Pocomoke City, MD

Onley Inn

Cottage near the Bay

Motel 6 Pocomoke City, MD

Find out more about Crisfield

Frequently asked questions