Crisfield Holiday Rentals

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Holiday Rentals in Crisfield

Cottage near the Bay
8.8 out of 10, Excellent, (49)
"great, peaceful "
The price is AU$295
includes taxes & fees
18 Oct - 19 Oct
Cottage near the Bay
Walk to Main St: Condo w/ Pool Access in Crisfield
9.2 out of 10, Wonderful, (7)
"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"
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
Whimsical Cottage with Gorgeous Views of the Bay, overlooking Russell Marina.
10.0 out of 10, Exceptional, (87)
"We had a great time at Colette’s and she was super communicative. Would recommend for a quiet, relaxing getaway!"
Whimsical Cottage with Gorgeous Views of the Bay, overlooking Russell Marina.
Cabin at Holdens Creek on Eastern Shore of VA
9.6 out of 10, Exceptional, (180)
"Beautiful, clean, quaint cabin.....only 25 minutes from Chincoteague island. Highly recommend. Thanks so much for the amazing place to stay!!!!"
Cabin at Holdens Creek on Eastern Shore of VA
The Porter's Barn - fancy little waterfront home with deep-water boat dock and firepit
10.0 out of 10, Exceptional, (35)
"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
Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly
9.6 out of 10, Exceptional, (22)
"Great clean place, beautiful views and fun activities!Owner is very responsive and communicates often. Bring your bug spray anywhere you go on the Eastern shore.Highly recommend for small family."
Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly
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
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 AU$302
includes taxes & fees
15 Oct - 16 Oct
A Little Serenity- A Cozy One Bedroom Escape in Quant Onancock,Mid-Eastern Shore
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock
10.0 out of 10, Exceptional, (17)
"Hubs and I were looking for a relaxing getaway and boy did we find it. This cottage was perfect. "
The price is AU$440
includes taxes & fees
15 Oct - 16 Oct
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock
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
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
Waterfront Retreat- Relaxing Family Fun! King Bed, Private Dock great 4 Fishing!
10.0 out of 10, Exceptional, (2)
"Very clean beautiful home lots of room. Family oriented. Beautiful view,plentiful parking space quiet peaceful relaxing pla e to stay. Highly recommend for a wonderful vacation or getaway. "
Waterfront Retreat- Relaxing Family Fun! King Bed, Private Dock great 4 Fishing!
Harbor Master-Waterfront 3 bedroom home with endless pool pickleball fenced yard
10.0 out of 10, Exceptional, (3)
"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
Beautiful, Waterfront, Luxury
9.6 out of 10, Exceptional, (5)
"Great place for a weekend away - house was beautiful and hosts were always quick to answer"
Beautiful, Waterfront, Luxury
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
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
Deal Island Bay Cottage
9.6 out of 10, Exceptional, (57)
"We got every year and stay here, it’s great! "
The price is AU$411
includes taxes & fees
14 Oct - 15 Oct
Deal Island Bay Cottage
Cozy Barn Loft: Country Views & Central to Beaches
10.0 out of 10, Exceptional, (18)
"Very clean and cozy home, they had all the necessary things we needed for our stay and we will certainly be staying there again if it’s available during our next visit. "
The price is AU$413
includes taxes & fees
14 Oct - 15 Oct
Cozy Barn Loft: Country Views & Central to Beaches
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

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 favourite 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 depend 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 AU$295 per night. Entering your travel dates in the search wizard might find you 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 Come, sit back and relax at the "Catch of the Bay" 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.