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Top Holiday Rentals in Crisfield

Cottage near the Bay

9.0 out of 10, Wonderful, (43)
"great, peaceful "
The price is £143
includes taxes & fees
17 Aug - 18 Aug
Cottage near the Bay

Walk to Main Street: Family-Friendly Crisfield Gem

10.0 out of 10, Exceptional, (2)
"Beautiful property"
Walk to Main Street: Family-Friendly Crisfield Gem

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

8.6 out of 10, Excellent, (4)
"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"
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"

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!

Cabin at Holdens Creek on Eastern Shore of VA

9.6 out of 10, Exceptional, (172)
"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 :( "
Cabin at Holdens Creek on Eastern Shore of VA

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (43)
"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!

Awesome private off grid cabin with creek view.

9.6 out of 10, Exceptional, (15)
"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.

Kayak friendly home on the Chesapeake Bay with paddle board and golf cart

9.8 out of 10, Exceptional, (11)
"Smith island is lovely! This house was perfectly located and furnished and the owner super helpful."
The price is £262
includes taxes & fees
17 Aug - 18 Aug
Kayak friendly home on the Chesapeake Bay with paddle board and golf cart

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

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

9.6 out of 10, Exceptional, (21)
"Perfect base to go out and explore and fish the Chesapeake. "
Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly

Pet-Friendly Smith Island Cottage w/ Golf Cart!

9.8 out of 10, Exceptional, (19)
"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!

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

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

10.0 out of 10, Exceptional, (15)
"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 £218
includes taxes & fees
1 Sept - 2 Sept
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock

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

10.0 out of 10, Exceptional, (13)
"This property was perfectly located in between Chincoteague Island and Janes Island State Park which were both destinations that I wanted to visit on my Spring Break. The property is rural and quiet. "
Serenity Cottage: Central to state parks, historic towns, MD & VA beaches

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

10.0 out of 10, Exceptional, (17)
"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

Beautiful Bayfront with Sanctuary Private Beach

9.2 out of 10, Wonderful, (20)
"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

Secluded waterfront getaway with hot tub,fire pit, and private dock.

10.0 out of 10, Exceptional, (8)
"This is such a lovely place for families to unwind and enjoy time together!"
Secluded waterfront getaway with hot tub,fire pit, and private dock.

Cozy Barn Loft: Country Views & Central to Beaches

10.0 out of 10, Exceptional, (18)
"Loft was spotless, and had everything we needed. "
The price is £201
includes taxes & fees
24 Aug - 25 Aug
Cozy Barn Loft: Country Views & Central to Beaches

Waterfront Maryland Retreat w/ Dock & Bay View!

9.8 out of 10, Exceptional, (9)
"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."
Waterfront Maryland Retreat w/ Dock & Bay View!
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

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.