Vacation rentals in Crisfield

4.94 out of 5 average rating, 488 reviews

A ceramic vase filled with a bouquet of fresh flowers is placed on a wooden countertop. The arrangement includes white magnolia blossoms, yellow coneflowers, and small orange flowers, providing a natural touch to the bathroom's decor.

Tiny home in Accomac

Little Red House on a Farm - Quiet Rural Waterview

The Little Red House VA is a cozy tiny home on a 50-acre farm, surrounded by fields, woods, marsh, and a creek. Curated with hygge comfort and efficiency, you'll love the natural light and calm decor. • Escape the noise & reset in nature • Peaceful sleeping • Thoughtful interior design • Large full bath • Comfy patio for coffee, cocktails, and epic stargazing • Firepit with wood provided • Large private outdoor shower surrounded by woods • Wide open spaces • Fast WIFI • Superhost for 10+ years

4.95 out of 5 average rating, 237 reviews

Two white adirondack chairs are positioned on a wooden dock, facing a calm waterway. Soft pastel colors in the sky reflect on the water, creating a serene atmosphere. The surrounding landscape features trees and distant hills, enhancing the peaceful waterfront view.

Cottage in Onancock

Eastern Shore Romantic Waterfront Getaway Upscale

A waterfront getaway at the newly renovated Westview Cottage on Onancock Creek just off the Chesapeake Bay. Wake up to beautiful water views through floor-to-ceiling glass doors. A private, peaceful escape in the country conveniently surrounded by fields and wildlife complete with a dock for crabbing and fishing (seasonal) 4 MI to Downtown Onancock & Restaurants 4.5 MI to Walmart 25 Mi to Camp Silver Beach 35 MI to Chincoteague Island 39 MI to Cape Charles >save listing to your wishlist<<

4.99 out of 5 average rating, 263 reviews

Farm stay in Onancock

Private romantic pet friendly waterfront cottage

On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

A cozy seating area is featured on the porch, showcasing a wicker loveseat with bright yellow cushions. Natural light filters in through the nearby window, and the surrounding greenery offers a serene backdrop.

4.96 out of 5 average rating, 52 reviews

Catch of the Bay

Welcome to the completely remodeled catch of the bay cottage! You will enjoy calling this beachy yet rustic location with a farmhouse theme your home during your stay. The home offers three bedrooms and one bathroom - one king bed, one queen bed, and a set of bunkbeds. There’s also a pull out couch if that more so meet your needs. The home offers a remodeled and fully stocked kitchen, laundry area/mudroom on the inside, as well as a spacious backyard, fire pit in front and rear porches.

4.96 out of 5 average rating, 287 reviews

Cozy Home near Waterfront in Crisfield, MD

Our home is close to great views, restaurants and shopping, the beach and family-friendly activities. You’ll love the sunsets over the water and viewing working boats in the harbor. Great for couples, solo adventurers, business travelers, and families (with kids). Beach is walking distance and the boat launch is 1/2 mile away. New library, playground, fishing, crabbing and gorgeous sunsets are all close by. Owners live only 15 minutes away for anything you may need.

Superhost

The image displays a serene sunset over a body of water, with the sun positioned low on the horizon. Silhouettes of trees and vegetation can be seen along the far shore, contrasting against the warm hues of orange and pink in the evening sky.

Guest suite in Crisfield

4.75 out of 5 average rating, 210 reviews

The Serenity House

Regenerate at the Serenity House! Second floor apartment; three spacious queen bedrooms with SmartTV, equipped kitchenette, work space with WiFi, mudroom and laundry on the first floor. Large yard with big mature shade trees nestled in a quiet neighborhood. One corgi and two cats live on the property. The pets are not allowed into the guest rooms. Continental breakfast served in the shared space. Private entrance, off street parking available.

4.99 out of 5 average rating, 227 reviews

A wooden boardwalk extends toward a sandy beach, flanked by tall grasses and wetlands. The peaceful water is visible in the distance under a clear blue sky, with a few clouds adding texture to the scene.

Cottage in Westover

Rumbley Cottage on the Tangier Sound-Private Beach

Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

4.98 out of 5 average rating, 162 reviews

A bright landing area with a sloped ceiling features a teal accent table and a mirror, complemented by decorative items and a lamp. A soft, light blue throw is casually draped over the railing, and warm hardwood flooring adds a touch of comfort.

Home in Tangier

Watermans Hideaway, Tangier Island, Chesapeake Bay

The Waterman’s Hideaway is a two story, coastal inspired home located on main street at the center of town and a short walk from Tangier’s restaurants, gift shops and tour boat docks. Guests can enjoy the deck overlooking the spacious backyard or lounge under the shade tree at the front of the property where they can interact with the locals passing bye as they go about their daily routines.

5 out of 5 average rating, 104 reviews

Home in Tangier

Island Oasis, Tangier Island, Virginia

Island Oasis is a one story, waterfront, newly renovated home situated in the heart of town. The tour boat docks are directly behind property with a gift shop on site. Restaurant, ice cream/sandwich deck, grocery store, church, museum , etc are all within walking distance. Guests will have full access to home and a nice deck overlooking harbor.

A wicker loveseat is displayed on a porch, featuring a striped cushion and two decorative pillows with a floral design. A small round table accompanies the seating, with brick flooring seen beneath. Light is visible through a nearby door leading indoors.

4.86 out of 5 average rating, 22 reviews

Cozy Crisfield Cottage

Your family will be close to everything when you stay at this centrally-located cottage located in the heart of Crisfield MD. Minutes away from Wellington Beach, the new bike trail, boat and kayak launch, Crab & Cruise and other attractions. Approximately an hour drive to Ocean City, Assateague and Chincoteague Island.

Guest suite in Deal Island Historic District

A spacious wrap-around deck features a wooden picnic table and a charcoal grill, enhancing outdoor dining options. A lounge chair is positioned nearby, creating an inviting spot for relaxation. The deck's wooden flooring extends along the side of the house, with a view of the surrounding greenery.

4.9 out of 5 average rating, 113 reviews

Private guest suite near Deal Island Maryland

Nothing extraordinary here. What I have available, at a reasonable rate is a clean private suite. With self check-in using kwikset smart code touchpad electronic deadbolt. Private driveway with plenty of room for your truck and boat. Room and deck are handicap accessible using entry ramp or steps.

4.96 out of 5 average rating, 134 reviews

A historical marker stands prominently, detailing the significance of Smith Island in Maryland's history. The marker features the state seal and provides information about its founding and early settlements. Background elements include fields and structures, indicative of the island's rural character.

Home in TYLERTON

3 bedroom/2.5 bath Smith Island bungalow with dock

The Quietness of the island and the beautiful scenery around the waters edge. You will hear the birds and the waves and the wind. The island is void of loud noises, mostly nature. The home was built around 1860 and fully restored 2008. its perfectly imperfect!

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Popular amenities for Crisfield vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Crisfield

Cottage in Marion Station

4.71 out of 5 average rating, 38 reviews

Year Round Playground - Rare Rustic-Modern Getaway

BrittanyRating, 5 stars1 day ago

Had a mini friend vacation with 6 people total and we all immediately felt right at home. The layout of the home is extremely convenient-there’s a half bath next to the washer/dryer right near the door to the deck- it was perfect for fast bathroom breaks without getting the entire house wet! We spent most of our time in the pool area and game room, and both spaces had everything we needed! (Nadia, I hope you don’t mind we left a few pool new loungers behind!) We took advantage of pretty much everything aside from swimming in the lake (bugs were really bad, no one’s fault at all but be warned- you NEED to have bug spray.) The only critique I could give was the softness of the beds, they were all really firm and if you have any sort of sleeping and or back/pain problems, it could be evident the next morning. But overall it was an amazing time and the host was extremely courteous and genuinely caring! A lot of love goes into this spot and you can tell. We can’t wait to go back.

5 out of 5 average rating, 44 reviews

Cabin in Westover

Chalet Style Home, private country setting

AprilRating, 5 stars3 months ago

I recently stayed at Crooked Elm and was thoroughly impressed. The place was impeccably clean, and the attention to detail was evident in every corner. The host's responsiveness was top-notch! One feature that stood out was the guest binder. It was incredibly detailed, providing clear instructions on everything from using the fireplaces to local attractions and dining recommendations. This made it easy to settle in and feel at home. It had everything we needed for a cozy stay! Overall, my stay at Crooked Elm was delightful, and I highly recommend it to anyone looking for a cozy, well-managed retreat.

4.96 out of 5 average rating, 53 reviews

A large tree with fresh green leaves stands prominently on a grassy area. In the background, Onancock Creek is visible, with a wooden dock extending into the water. Clear blue skies complement the serene landscape, enhancing the outdoor view.

Guesthouse in Onancock

Holly Cove’s “Tiny” Guesthouse

HugoRating, 5 stars1 week ago

Just returned from an amazing two-day stay at Martha's guest home. While the house is small, it's thoughtfully designed and incredibly comfortable. The setting is absolutely beautiful and tranquil — just a short walk to the water, where we swam, paddled kayaks, and relaxed on the wooden pier. Evenings with bubbly and mornings with coffee by the water made for unforgettable moments. Although the guest house is next to the hosts’ property, it still felt wonderfully private. Martha and Buck were warm, welcoming, and always ready to help with anything we needed. This is a perfect spot to unwind and reconnect with nature. Highly recommended!

4.99 out of 5 average rating, 89 reviews

Two goats are positioned on a small white platform, displaying distinct black and brown fur. The goats stand against a backdrop of green grass and trees, with a wire fence delineating the area. The sky is clear and blue.

Loft in Pocomoke City

Cozy Barn Loft: Country Views & Central to Beaches

KristaRating, 5 stars2 weeks ago

We really enjoyed our stay at the loft! It was right like the pictures and it was very clean. the farm fresh eggs were a fun touch! :) The fun little touches, like the snacks on the table, the eggs in the fridge and the binder of local things to do were really appreciated! highly recommend this place!

4.94 out of 5 average rating, 50 reviews

An upper view reveals a rustic cabin interior with wooden walls and a high sloped ceiling. A ceiling fan hangs above, and a stone fireplace is visible adjacent to a sliding glass door leading outside. A dining table and rocking chair are situated nearby.

Cabin in Onancock

Awesome private off grid cabin with creek view.

DanielRating, 5 stars3 weeks ago

This place was as described. Very peaceful get away for my family and totally worth the price we paid. Teresa was quick to respond and recommended some place to eat. We will be back to experience the fall weather.

The exterior of a three-story home features a front porch with steps leading to the entrance. A lawn surrounds the house, while a tree without leaves stands in the yard. An American flag is displayed in front, and blue skies are visible above.

4.94 out of 5 average rating, 33 reviews

Myrtle Manor- Crisfield Maryland

MichaelRating, 5 stars1 month ago

My family absolutely loved the house. Very clean, very private with the backyard parking, and right in the center of town. Would rebook again and again!

5 out of 5 average rating, 11 reviews

Home in Saxis

Island Jewell Near Chincoteague

MichelleRating, 5 stars7 months ago

My husband and I booked a last minute anniversary trip and Denise's home was absolutely perfect. This little home was everything that you could want and more for peace and relaxation. Denise was helpful and responsive and accomodated a very late night check in with no problems!