Crisfield Holiday Rentals

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Holiday Rentals in Crisfield

Cottage near the Bay
9.0 out of 10, Wonderful, (13)
"Come stay at this wonderful house in lovely Crisfield Maryland. You won't be sorry. The host is fantastic and gets back to you quickly if you have questions. Thank you for everything."
The price is NZ$324
includes taxes & fees
3 Jun - 4 Jun
Cottage near the Bay
Waterfront 3 bedroom condo. Spring is here!
10.0 out of 10, Exceptional, (19)
"Crisfield is home. The condo made visiting family easy. Thank you!"
Waterfront 3 bedroom condo. Spring is here!
Come, sit back and relax at the "Catch of the Bay"
10.0 out of 10, Exceptional, (3)
"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"
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Stylish Condo with a Great View
10.0 out of 10, Exceptional, (4)
"The property is in a great locationwith beautiful sunsets. It was perfect for a thanksgiving trip."
The price is NZ$567
includes taxes & fees
12 Jun - 13 Jun
Stylish Condo with a Great View
Simply the best...Beautiful condo overlooking the Chesapeake bay.
10.0 out of 10, Exceptional, (101)
"The condo was perfect. Checkin was easy, was as described and the view was amazing. Would recommend to anyone looking for a relaxing getaway"
Simply the best...Beautiful condo overlooking the Chesapeake bay.
Beautiful 3 bedroom waterfront condo, top floor- overlooking the Chesapeake Bay!
Beautiful 3 bedroom waterfront condo, top floor- overlooking the Chesapeake Bay!
Victorian Get Away
Victorian Get Away
BEAUTIFUL REMODELED "COTTAGE BY THE BAY" in CRISFIELD! WE STRIVE TO BE THE BEST!
10.0 out of 10, Exceptional, (3)
"The property was very beautiful! Enjoyed the stay and communication with the host was excellent!"
BEAUTIFUL REMODELED "COTTAGE BY THE BAY" in CRISFIELD! WE STRIVE TO BE THE BEST!
Breathtaking Top Floor Waterfront Condo with Wrap Around Balcony and Boat Slip
9.8 out of 10, Exceptional, (59)
"Great location and views. Condo was clean and exactly as the description says. Owners were quick to call back when I reached out. Would definitely rent again."
Breathtaking Top Floor Waterfront Condo with Wrap Around Balcony and Boat Slip
Beautiful Waterfront Condo w/ Community Pool!
9.8 out of 10, Exceptional, (9)
"Loved the condo. Well furnished, exceptionally clean and well stocked. Porches are perfect for relaxing, reading or a cocktail whatching sunset. Will be back for sure."
Beautiful Waterfront Condo w/ Community Pool!
Cozy Contemporary Home
The price is NZ$839
includes taxes & fees
1 Jun - 2 Jun
Cozy Contemporary Home
NEWLY REMODELED COZY APARTMENT with WATER VIEWS & AMAZING SUNSETS in CRISFIELD!!
NEWLY REMODELED COZY APARTMENT with WATER VIEWS & AMAZING SUNSETS in CRISFIELD!!
Beautiful Bayfront with Sanctuary Private Beach
9.2 out of 10, Wonderful, (10)
"House was exactly as advertised and expected. Would stay agian for sure"
The price is NZ$647
includes taxes & fees
2 Jun - 3 Jun
Beautiful Bayfront with Sanctuary Private Beach
Cabin at Holdens Creek on Eastern Shore of VA
9.6 out of 10, Exceptional, (145)
"We get together once a year, 5 guys, to hang out, catch up, shoot skeet, target shoot and fish. We do this at a different location every year. This location worked out great. It was private, allowed shooting and had enough room to sleep 5. We would use this cabin again!"
Cabin at Holdens Creek on Eastern Shore of VA
As close as you can get to the ocean south of Chincoteague
10.0 out of 10, Exceptional, (123)
"The house was perfect for our family’s long weekend stay in April 2024. The location is splendid for its views, water accessibility and peace and quiet. We kayaked to the barrier island (approx.15 min) and found many pristine whelk sea shells. We thoroughly enjoyed crabbing and fishing in the creek as well bird watching. The homeowners really have provided just about everything you could ask for as far as amenities and supplies. Additionally they were very helpful and informative when we had...
The price is NZ$820
includes taxes & fees
11 Jun - 12 Jun
As close as you can get to the ocean south of Chincoteague
Pet-Friendly Quantico Home w/ River Views!
10.0 out of 10, Exceptional, (2)
"Beautifully decorated and clean spacious waterfront house with plenty of amenities. Plenty of rooms and outdoor areas to enjoy."
Pet-Friendly Quantico Home w/ River Views!
Quaint Island Getaway
10.0 out of 10, Exceptional, (11)
"This is a charming place, full of really nice interior touches. The location gives you access to some great marshland so you are treated to a daily dose of great bird sightings, including ospreys, red-winged blackbirds, herons and others. The house has everything you need. The only advice I would give - to remind guests to clean off the grill when they are done using it. We had to clean it thoroughly as it had obviously not been cleaned in awhile. I suggest you add that to the short list of...
Quaint Island Getaway
Rock Hall on the water
9.4 out of 10, Exceptional, (42)
"We were scouting this house as a potential place to bring friends, and while we really liked the house there are a few things we noticed that might make us hesitant to bring a larger group. The ground floor was badly in need of vacuuming and there was hair in the shower drain. We never could connect to internet and had no cell service so couldn't even let anyone know. Finally, the water has a highly sulfur odor. Overall it seemed no-one had been in the house in a while and it needed some more...
Rock Hall on the water
Awesome private off grid cabin with creek view.
9.4 out of 10, Exceptional, (9)
"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.
Inviting Waterfront Cottage on Cedar Creek
10.0 out of 10, Exceptional, (25)
"Three family groups - 5 adults and one toddler - lot of room so not on top of each other - we cooked in all weekend - nicely equipped kitchen, roomy dining table (also great for games and cards). Thoroughly enjoyed the porch room - beautiful view. Walked around the yard with the toddler - spacious. Used the kayaks - nice to have that option. Took some walks - nice area. Next door neighbor - not close, but was playing loud music while setting up for a party, a minor irritant. During the party...
Inviting Waterfront Cottage on Cedar Creek
Don't see what you're looking for?
See all available properties in Crisfield
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.

Other types of properties in Crisfield you may be interested in

Cottage near the Bay
9.0 out of 10, Wonderful, (13)
"Come stay at this wonderful house in lovely Crisfield Maryland. You won't be sorry. The host is fantastic and gets back to you quickly if you have questions. Thank you for everything."
The price is NZ$324
includes taxes & fees
3 Jun - 4 Jun
Cottage near the Bay
Home of the Terrapin King
9.4 out of 10, Exceptional, (104)
"If you are looking for a home with history and charm that’s away from it all, the Home of the Terrapin King is it. Because the house is on a peninsula, you are away from the hustle and bustle of a typical town. There is plenty to enjoy some quality family/friend time. The house itself could use a little TLC as any rental would periodically need and considering it’s a 100+ year old house, but it is perfectly decorated in keeping with the Eastern Shore area. The views are incredible, especially...
Home of the Terrapin King
Waterfront 3 bedroom condo. Spring is here!
10.0 out of 10, Exceptional, (19)
"Crisfield is home. The condo made visiting family easy. Thank you!"
Waterfront 3 bedroom condo. Spring is here!
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Crisfield holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Crisfield. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Crisfield. Seeing all the best attractions is bound to make you fall in love with Crisfield. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Crisfield short-term rentals, that won’t be hard to do.

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 5 Expedia holiday rentals in Crisfield for a memorable holiday.

What’s there to see and do in Crisfield?

Enjoy the area's cultural attractions such as J. Millard Tawes Museum, or get outdoors into nature at a spot like Smith Island. In the wider area, you’ll find Somers Cove Marina and Tangier Island.

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.

Recent reviews of Crisfield properties
Expedia verified reviews