Crisfield Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 13 - Aug 14
Tomorrow
Aug 14 - Aug 15
This weekend
Aug 15 - Aug 17
Next weekend
Aug 22 - Aug 24

Vacation Rentals in Crisfield

Cottage near the Bay
Dining

Cottage near the Bay

9.0 out of 10, Wonderful, (41)
"great, peaceful "
The price is ￥11,971
￥27,885 total
includes taxes & fees
Aug 17 - Aug 18
Cottage near the Bay
Walk to Main Street: Family-Friendly Crisfield Gem
Fridge, microwave, stovetop, dishwasher

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
Marina

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"
Terrace/patio

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!
Outdoor dining

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
Interior

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!
Beach

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.
Outdoor dining

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.
Home on Smith Island in the Chesapeake Bay with golf cart, kayaks and SUP
Interior

Home on Smith Island in the Chesapeake Bay with golf cart, kayaks and SUP

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 ￥29,494
￥46,345 total
includes taxes & fees
Aug 14 - Aug 15
Home on Smith Island in the Chesapeake Bay with golf cart, kayaks and SUP
Near Chincoteague & Assateague Island Charming 2-bedroom cottage
Outdoor dining

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
Outdoor dining

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!
Interior

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
Terrace/patio

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
Property grounds

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 ￥28,790
￥42,870 total
includes taxes & fees
Sep 1 - Sep 2
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock
Serenity Cottage: Central to state parks, historic towns, MD & VA beaches
Fridge, microwave, oven, stovetop

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
Exterior

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
Property grounds

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.
Outdoor spa tub

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
1 bedroom, desk, travel crib, WiFi

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 ￥19,287
￥38,306 total
includes taxes & fees
Aug 14 - Aug 15
Cozy Barn Loft: Country Views & Central to Beaches
Waterfront Maryland Retreat w/ Dock & Bay View!
Marina

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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Crisfield Hotel Reviews

Regal Inn

Regal Inn

10/10 Excellent
"I like it there"
Markice 2-night trip
Posted 18 hours ago
Regal Inn

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.