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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Browse Select Crisfield Vacation Homes

Cottage near the Bay
Enjoy cooking and dining in this well-equipped kitchen with a central island and dining table.

Cottage near the Bay

9.0 out of 10, Wonderful, (39)
"great, peaceful "
The price is CA $111
CA $258 total
includes taxes & fees
Aug 13 - Aug 14
Cottage near the Bay
Historic home on Smith Island w/ dock!
Enjoy serene views of the calm water from the dock, surrounded by a peaceful shoreline.

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!
Get away to relax on Smith Island in the Chesapeake Bay with golf cart included
Interior

Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

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 $273
CA $430 total
includes taxes & fees
Aug 11 - Aug 12
Get away to relax on Smith Island in the Chesapeake Bay with golf cart included
Beautiful Bayfront with Sanctuary Private Beach
Relax on the deck with a clear view of the surrounding grassy field and trees.

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
Walk to Main Street: Family-Friendly Crisfield Gem
Enjoy cooking in this well-equipped kitchen with a central island, oven, and stainless steel range hood.

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
Secluded waterfront getaway with hot tub,fire pit, and private dock.
Relax in the hot tub on the deck overlooking the serene lake and surrounding trees.

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
Cozy retreat with a central cabinet, comfortable bed, and woven rugs.

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 CA $180
CA $360 total
includes taxes & fees
Aug 13 - Aug 14
Cozy Barn Loft: Country Views & Central to Beaches
Home in historic Whitehaven Village.
Enjoy cooking in this well-equipped kitchen with a granite countertop, double oven, and range.

Home in historic Whitehaven Village.

10.0 out of 10, Exceptional, (4)
"Great stay! Nice and relaxing and owner fast response with questions!"
Home in historic Whitehaven Village.
Creek House - Waterfront Oasis on Holden's Creek
Enjoy meals in this dining area with a large table and six chairs, surrounded by a high ceiling and large windows offering views of the surrounding landscape.

Creek House - Waterfront Oasis on Holden's Creek

9.6 out of 10, Exceptional, (10)
"Beautiful Home, Great Location, Great Communication with Vrbo and the owner. All appliances were up to date and easy to use. "
Creek House - Waterfront Oasis on Holden's Creek
Inviting Waterfront Cottage on Cedar Creek
Relax in Adirondack chairs overlooking the serene lake.

Inviting Waterfront Cottage on Cedar Creek

10.0 out of 10, Exceptional, (37)
"We had a wonderful stay. We enjoyed the kayaks and the firepit as well as a few local restaurants. The house was clean and the host was very responsive. "
Inviting Waterfront Cottage on Cedar Creek
Waterfront Retreat- Relaxing Family Fun! King Bed, Private Dock great 4 Fishing!
Outdoor dining

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!
Harbor Master-Waterfront 3 bedroom home with endless pool pickleball fenced yard
Relax with a view of the water from this outdoor seating area, featuring two comfortable chairs and a small table.

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
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD
Enjoy meals in this inviting dining area with a long table for four, a chandelier, and a sign highlighting fresh local seafood.

Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

2.0 star property
9.8 out of 10, Exceptional, (8)
"Very clean and charming home we will be back again! "
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD
Waterfront Estate - Amazing Views And Sunsets - Pet Friendly - New rate for 2025
Enjoy a relaxing moment on the covered porch with a bench and Adirondack chairs.

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
Guests can enjoy a serene riverside view from the deck overlooking the calm river surrounded by lush greenery and trees.

Par-Lon - Private Raised Waterfront Home on the Pocomoke River

2.0 star property
10.0 out of 10, Exceptional, (3)
"Had an amazing time here very piecefull and beautiful "
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
Relax in a serene outdoor space with two Adirondack chairs on a spacious patio surrounded by tall pine trees.

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

10.0 out of 10, Exceptional, (32)
"Beautiful panorama!"
The Porter's Barn - fancy little waterfront home with deep-water boat dock and firepit
Family Friendly Waterfront Escape w/pier, gameroom, and fire pit!
Enjoy meals in the kitchen with a central island and dining area, featuring a refrigerator, dishwasher, and wooden countertop.

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!
Bayfront Beauty with Beach and Boatslip!!
Enjoy a room with a high ceiling, large windows, and a comfortable seating area.

Bayfront Beauty with Beach and Boatslip!!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Highly recommend, very communicative host, the place is better than shown. Great views, private boat slip. The community right next to it is nice with a little local pub. "
Bayfront Beauty with Beach and Boatslip!!
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and coffee maker, surrounded by a round table and four chairs.

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

10.0 out of 10, Exceptional, (25)
"Wonderful stay and beautiful accomodations"
The price is CA $209
CA $437 total
includes taxes & fees
Aug 13 - Aug 14
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
Quaint Island Getaway
Enjoy a serene beach experience with breathtaking ocean views.

Quaint Island Getaway

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

The Charlotte Hotel & Restaurant

The Charlotte Hotel & Restaurant

10/10 Excellent
"The room was just what we needed for over-night. Very comfortable king sized bed and a great shower. Quiet too. We would stay here again. "
Penny 1-night trip
Posted 3 days ago
The Charlotte Hotel & Restaurant