Crisfield Holiday Rentals

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Holiday Rentals in Crisfield

Our top choices for Crisfield holiday rentals

Cottage near the Bay

8.8 out of 10, Excellent, (46)
"great, peaceful "
The price is NZ$318
includes taxes & fees
1 Oct - 2 Oct
Cottage near the Bay

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

9.0 out of 10, Wonderful, (6)
"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

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"

Charming Cottage - Ultimate Relaxation Destination

10.0 out of 10, Exceptional, (124)
"Very nice cute cottage, well stocked. only downfall is that windows don't open in some of the rooms due to age and excess paint."
Charming Cottage - Ultimate Relaxation Destination

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

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (45)
"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!

Cabin at Holdens Creek on Eastern Shore of VA

9.6 out of 10, Exceptional, (180)
"Thank you for your hospitality!! Your rental property is absolutely amazing! We love cabins and yours made us feel so at home. We are looking forward to visit again!"
Cabin at Holdens Creek on Eastern Shore of VA

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

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

10.0 out of 10, Exceptional, (33)
"Beautiful, private, relaxing! We loved our stay! The only thing and reason we say 4 stars is we would have loved privacy curtains on the large and small windows. "
The Porter's Barn - fancy little waterfront home with deep-water boat dock and firepit

Creek House - Waterfront Oasis on Holden's Creek

9.8 out of 10, Exceptional, (12)
"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

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

10.0 out of 10, Exceptional, (3)
"Very convenient location and Steve was very attentive to our needs - even the dog enjoyed the stay."
The price is NZ$333
includes taxes & fees
29 Sept - 30 Sept
A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore

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

10.0 out of 10, Exceptional, (57)
"Enjoyed the well stocked home filled with everything from kayaks, sun umbrellas and chairs to big spray. Had a wonderful time!"
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, (18)
"Micky and Kim were great hosts and the house was awesome. They were very accommodating. Will definitely be back! "
IDLE HOUR, a tranquil 3 bedroom 1.5 bath cottage WITH DOCK

Waterfront Historic Gem w/ Kayaks & Fire Pit

8.6 out of 10, Excellent, (4)
"Great house. Clean. Had everything we needed."
Waterfront Historic Gem w/ Kayaks & Fire Pit

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

Chesapeake Bay Retreat Private Dock + Beach

10.0 out of 10, Exceptional, (3)
"Wonderful house and phenomenal lot. Very well appointed and extremely well stocked. The lot is absolutely amazing…private, serene and gorgeous views on the water. We’ll definitely return."
Chesapeake Bay Retreat Private Dock + Beach

Whimsical Cottage with Gorgeous Views of the Bay, overlooking Russell Marina.

10.0 out of 10, Exceptional, (85)
"We enjoyed our stay at the Farmhouse! The owners were great to communicate with, they give wonderful advice of things to do and places to eat on the Eastern Shore! We would definitely recommend staying here if you are visiting the area! "
Whimsical Cottage with Gorgeous Views of the Bay, overlooking Russell Marina.

Beautiful Bayfront with Sanctuary Private Beach

9.2 out of 10, Wonderful, (24)
"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

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

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

10.0 out of 10, Exceptional, (2)
"What a great stay! Nice location and very quiet. Thoughtful kitchen amenities were appreciated. Definitely worth a return stay!!"
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 Crisfield Hotel Reviews

Find out more about Crisfield

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, 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 NZ$318 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.

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.