Crisfield Vacation Rentals

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Vacation Rentals in Crisfield

Cottage near the Bay

9.0 out of 10, Wonderful, (43)
"great, peaceful "
The price is CA $112
CA $262 total
includes taxes & fees
Aug 24 - Aug 25
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!

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

9.6 out of 10, Exceptional, (22)
"Perfect base to go out and explore and fish the Chesapeake. "
Charming Waterfront Cottage with Boat Ramp and boat docking - Pet Friendly

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

10.0 out of 10, Exceptional, (15)
"Hubs and I were looking for a relaxing getaway and boy did we find it. This cottage was perfect. "
The price is CA $243
CA $367 total
includes taxes & fees
Sep 1 - Sep 2
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock

Charming Cottage - Ultimate Relaxation Destination

10.0 out of 10, Exceptional, (119)
"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!"
Charming Cottage - Ultimate Relaxation Destination

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

Beautiful Bayfront with Sanctuary Private Beach

9.2 out of 10, Wonderful, (21)
"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

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!

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

10.0 out of 10, Exceptional, (18)
"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

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

Awesome private off grid cabin with creek view.

9.8 out of 10, Exceptional, (16)
"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.

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!

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & 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 CA $312
CA $478 total
includes taxes & fees
Sep 1 - Sep 2
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

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

10.0 out of 10, Exceptional, (57)
"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!"
Waterfront Estate - Amazing Views And Sunsets - Pet Friendly - New rate for 2025

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
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 vacation rentals in Crisfield?

Yes, we have vacation rentals close to the most popular attractions in Crisfield, or you can select a more remote option if you want a relaxing place to stay. Our travelers 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 vacation rentals in Crisfield?

Cottage near the Bay: This highly rated vacation home rental in Crisfield is equipped with a barbecue grill, 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 you can cook with friends or family. Our travelers also rate Walk to Main Street: Family-Friendly Crisfield Gem as a favorite home for rent in Crisfield.

How many vacation rentals will I find in Crisfield?

Choose from 4 Expedia vacation rentals in Crisfield for a memorable vacation.

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 vacation rental in Crisfield like?

Vacation rentals are private properties where you can stay for a few weeks or just a few days in Crisfield. Vacation rentals feature extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.