Vacation rentals in Crisfield

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Top-rated vacation rentals in Crisfield

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Top guest favorite
An aerial view highlights Rumbley Cottage's proximity to the shoreline and wetlands. The landscape features a mix of sandy beach, shallow waters, and expansive marshlands under a clear blue sky, offering a serene setting with natural beauty and tranquility.
Cottage in Westover
4.99 out of 5 average rating, 255 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

Three shorter stays available: July 19-21, October 23-26 and November 11-14. Message me so I can send special invite. 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. Many amenities: WE PROVIDE THE FIREWOOD AND STARTERS, kayaks, paddle boards, MB toiletries.

Top guest favorite
The exterior of a modern, single-story house features a light blue façade with contrasting dark shingles. A wooden staircase leads to the front door, while a small deck is visible to the left. A paved walkway runs along the well-maintained lawn.
Home in Crisfield
4.99 out of 5 average rating, 98 reviews

Marshall’s Retreat Chesapeake small town getaway

Modern 3 bedroom home centrally located in the heart of Crisfield, Md. Off & on street parking. Minutes from our towns new bike trail, boat & Kayak launch, park play ground,Wellington Beach, shopping, Ferry’s to The Islands, fishing piers, restaurants, Crab & Cruise (within walking distance), beautiful views. about an hour drive to Ocean City, Assateague or Chincoteague. Or stay in & relax watch Cable tv, Wifi. Please be sure to research the area online to make sure it’s right for your needs.

Top guest favorite
A Victorian cottage sits on a private island, surrounded by a serene lake. The green roof contrasts with the pastel exterior, while a footbridge leads to the shore. Lush grass and scattered trees create a peaceful landscape, with distant water views enhancing the setting.
Cottage in Hacksneck
4.95 out of 5 average rating, 152 reviews

Pretty Byrd Cottage, a Victorian Bayfront Getaway!

Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and a balcony that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!

Top guest favorite
A wooden deck is shown overlooking a serene pond, framed by lush trees. A dining table with chairs is set for outdoor enjoyment, while soft natural light reflects off the water's surface, creating a peaceful ambiance.
Farm stay in Onancock
4.99 out of 5 average rating, 334 reviews

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!

Top guest favorite
A rustic treehouse is elevated among tall trees, featuring a front porch with a railing and multiple windows. Below, a seating area is arranged with bright blue chairs and a black coffee table, surrounded by a natural forest setting.
Treehouse in Machipongo
4.98 out of 5 average rating, 115 reviews

The Waverly Treehouse

Reconnect with nature and sway with the trees in this rustic treehouse nestled away in the woods with a gorgeous view of Hungar's creek. Enjoy the view from the front porch or while relaxing around the fire pit. Visit the adorable beach town of Cape Charles, complete with a beautiful beach, brewery, distillery and plenty of restaurant options, or stop by the nearby vineyard for some local wine. Usage of dock, kayaks, grill, and fire pit all included. Beach towels and cooler also provided.

Superhost
Farm stay in Crisfield
4.85 out of 5 average rating, 34 reviews

Home of The Terrapin King

The LaVallette House is where the Maryland terrapin originated! Albert Tallmadge LaVallette Jr. launched the terrapin soup industry from this very site in 1887 (you can still see the old terrapin pins beside the driveway). In addition to the property’s historic charm, the location just can’t be beat. The five-bedroom house is completely private. Guests have to drive through wetlands to get to it, and the only neighbors in close proximity are the gulls and the fish in the Chesapeake Bay.

Guest favorite
A light-colored couch with striped black and white pillows is positioned in a spacious living area. A round, dark wood coffee table sits in front of the couch, accompanied by a soft area rug. Natural light enters through two nearby windows, illuminating the room.
Home in Crisfield
4.96 out of 5 average rating, 74 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.

Guest favorite
The exterior of a two-story house is shown, featuring a light-colored façade and multiple windows. A staircase leads to an entrance at the front. A well-maintained lawn surrounds the structure, and a friendly corgi is visible on the grass.
Guest suite in Crisfield
4.78 out of 5 average rating, 265 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.

Superhost
A charming two-story house is situated in a grassy area, featuring red shutters and a sign reading 'Island Breeze Vacation Rental' in front. Flower beds with vibrant blooms surround the sign. A porch with steps leads to the entrance of the home.
Cottage in Saxis
4.85 out of 5 average rating, 143 reviews

ISLAND BREEZE Near Chincoteague Island

Waterman’s fishing village Surrounded by water on three sides & Virginia Wildlife Refuge on fourth side. Walking distance to beach (located on Dennis Lane) Kayaking & Canoeing Wildlife Fishing Pier Boat Ramp Marina Public Pavilion Ice Cream Shop 1-Restaurant (Capt E’s Hurricane Grill & Tiki Bar) Museum Multiple Seafood Shanty’s (Steamed Crabs Available during season)

Top guest favorite
The exterior of the cottage is shown, featuring a welcoming entryway with stairs and a blue door. Two blue adirondack chairs are positioned on the well-maintained lawn, with a glimpse of the waterfront visible through large windows. Surrounding greenery enhances the outdoor setting.
Cottage in Smith Island
4.97 out of 5 average rating, 252 reviews

Levering Creek Cottage with private dock

Levering Creek Cottage is a waterfront property with a deep water dock that you can see from the back door. We are located on Levering Creek where you can sit on the dock watching watermen arrive with their daily catch, see nesting bald eagles, watch beautiful sunrise, fish and crab. We are also just steps away from most everything including the ferry.

Top guest favorite
A one-story white house is surrounded by a green lawn and is enclosed by a fence. The home features a peaked roof and small front porch, with large windows allowing natural light. A decorative sign is positioned in front, marking the property.
Home in Tangier
5 out of 5 average rating, 149 reviews

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.

Guest favorite
A charming two-story cottage features a traditional white exterior with black shutters framing multiple windows. A welcoming front porch is accessed by a brick pathway, while a mailbox stands at the edge of the neatly maintained lawn. Stately trees provide a backdrop.
Home in Crisfield
4.91 out of 5 average rating, 54 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.

Popular amenities for Crisfield vacation rentals

  1. Airbnb
  2. United States
  3. Maryland
  4. Somerset County
  5. Crisfield