Holiday Homes in Crisfield

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Featured Holiday Homes in Crisfield

Our top choices for Crisfield holiday homes

Cottage near the Bay

9.0 out of 10, Wonderful, (43)
"great, peaceful "
The price is NZ$320
includes taxes & fees
7 Sept - 8 Sept
Cottage near the Bay

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (45)
"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!

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

Beautiful Bayfront with Sanctuary Private Beach

9.2 out of 10, Wonderful, (22)
"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

Blue Heron - A Breathtaking Eastern Shore Vacation Experience!

9.8 out of 10, Exceptional, (32)
"Had a very pleasant few days in this house celebrating a birthday. The area is relaxing and calm, beautiful views and the house was so cozy!"
Blue Heron - A Breathtaking Eastern Shore Vacation Experience!

Chesapeake Bay Retreat Private Dock + Beach

10.0 out of 10, Exceptional, (1)
"Came to the eastern shore for a wedding-could not have found a better property or owner! Great communication, property was better than advertised—we will be back!! Thanks so much to Genevieve for being so attentive and helpful!!!"
Chesapeake Bay Retreat Private Dock + Beach

Harbor Master-Waterfront 3 bedroom home with endless pool pickleball fenced yard

10.0 out of 10, Exceptional, (1)
"Peaceful, relaxing place with wonderful waterfront views. House is spacious and well-stocked, with a large fenced yard. We enjoyed catching fish and blue crabs right from the dock and kayaking on the river. Highly recommend. "
Harbor Master-Waterfront 3 bedroom home with endless pool pickleball fenced yard

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!

Home in historic Whitehaven Village.

10.0 out of 10, Exceptional, (5)
"We thoroughly enjoyed our time in Whitehaven. It was a nice place to unwind and unplug."
Home in historic Whitehaven Village.

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

9.8 out of 10, Exceptional, (12)
"The perfect place to wind down, reconnect with people, culture and a way of life we’ve strayed away from. The house was amazing! The town, the good people and the atmosphere just as much. "
The price is NZ$586
includes taxes & fees
11 Sept - 12 Sept
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

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

The Porter's Barn - fancy little waterfront home with deep-water boat dock and firepit

10.0 out of 10, Exceptional, (33)
"Beautiful panorama!"
The Porter's Barn - fancy little waterfront home with deep-water boat dock and firepit

Creek House - Waterfront Oasis on Holden's Creek

9.8 out of 10, Exceptional, (11)
"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

Family Friendly Waterfront Escape w/pier, gameroom, and fire pit!

9.4 out of 10, Exceptional, (6)
"The property was perfect for a very relaxing weekend. The house was exactly what we needed for our little group."
Family Friendly Waterfront Escape w/pier, gameroom, and fire pit!

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

10.0 out of 10, Exceptional, (57)
"First, the house is clean, well-stocked with the comforts of home, and architecturally stunning in a classic/traditional way. The sunsets are amazing. The breezes off the bay are refreshing. The whole property has a sense of peace. As a young man, I grew up fishing the many lakes, bays and marshlands of Louisiana …. also I worked and played on my grandfather’s farm in Virginia. This plays combines the two, magnificently. My wife, our two young boys, and the dog were at ease in this wonderful...
Waterfront Estate - Amazing Views And Sunsets - Pet Friendly - New rate for 2025

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 NZ$447
includes taxes & fees
15 Sept - 16 Sept
Cozy Barn Loft: Country Views & Central to Beaches

Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

10.0 out of 10, Exceptional, (26)
"Wonderful stay and beautiful accomodations"
The price is NZ$539
includes taxes & fees
7 Sept - 8 Sept
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

Vacation home near the beaches!.

10.0 out of 10, Exceptional, (2)
"Nice and clear peaceful place to enjoy your vacation!"
Vacation home near the beaches!.

Quaint Island Getaway

10.0 out of 10, Exceptional, (13)
"We enjoyed our stay. The property was clean and cozy."
Quaint Island Getaway

Waterfront Historic Gem w/ Kayaks & Fire Pit

8.6 out of 10, Excellent, (4)
"Great house. Clean. Had everything we needed."
Waterfront Historic Gem w/ Kayaks & Fire Pit
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

Find out more about Crisfield

Crisfield Holiday Homes information

Number of reviews
Accommodation
57 Holiday Homes
Lowest Price
NZ$320
Highest Price
NZ$586