Condo vacation rentals in Crisfield

An Assateague Adventure

Please give us the opportunity to host you in our modest home drenched in colors inspired by our island sunsets. Located along Eel Creek which feeds into Little Oyster Bay, this 2BR/2BA condo is on the top floor, providing breathtaking marsh views from the condo, and your private side deck to enjoy coffee in the morning or a beverage to close our your evening. Pool & bbq area. Birding paradise. Located on Coach’s Lane at the Assateague Inn- it provides easy pier access for fishing and crabbing.

Water view at Ocean Pines Yacht Club Condo

Steps to 2 pools, 2 marinas, tiki bar and OP Yacht Club. Live music Thursday-Sunday evenings from 6-10pm, (in season). Beach day? Ocean City 15 min drive or walk to the marina and hop on a boat with friends and head across the bay into OC. Assateague Island is a 20 min drive. Crabbing? Fishing? Walk to one of the many Ocean Pines canals or ponds. Golfing? The links are just across the Parkway. Wedding party? Be footsteps away from make lasting memories. Free beach parking on 49th included

*+Updated 5* Bayside 3BR Condo by Sun Ridge pool+*

Roomy 3 Bed, 2 Bath Condo in the heart of Bayside. Sleeps up to 8 people. Well-stocked kitchen, comfortable living area and a screened in porch. Dedicated high speed internet & 3 streaming TV's. Elevator access with one reserved, covered parking spot. Additional parking in front of bldg. STEPS from the Sun Ridge Community Pools and Rec. Center- complete with a splash pad, 2 pools, sports courts and more! Passes for use of the pool & rec. facilities are sold at cost for either 3 or 7 day use.

Condo Bayside Resort, Fenwick Island

Beautiful, updated condo at the Bayside resort in Fenwick Island, DE. Only minutes from the beach and borders the Bay. Located on the border of DE and MD with easy access to Ocean City and all the beach towns including Bethany, Dewey Rehoboth, and Lewes. The Bayside resort offers an abundance of amenities such as golf, 4 outdoor swimming pools, indoor pool & fitness center, tennis & pickleball courts, hiking trails and more. PLEASE NOTE: Guest passes are $20 per person for resort amenities.

The Little Paradise-Waterfront, pet-friendly Studio

Le Petit Paradis is our cozy 300 sqft, 2nd floor studio apartment on Marsh Island, Chincoteague and we're excited to share it with you! 🏝 Expansive water views 🌅 gorgeous sunsets 🐶 pets welcome (no pet fee) 🛋 modern furnishings that maintain the "stuck in time" charm of the Island 📱 standard amenities (including WiFi and smart TV) 🛌 Linens and toiletries included 🦆 Plentiful wildlife (ducks, turtles, island cats & more) No balcony but there is a shared dock / patio grill.

The Solomons Sunrise Suite

Centrally Located to all that Solomons Island has to offer! This 2 Bedroom 2 Bathroom Luxury suite is equipped with a gourmet kitchen, a very large family room with vaulted ceilings, and a covered rear porch with views of Back Creek, The Patuxent River, & a glimpse out to the Chesapeake Bay. Elegant Furnishings make this bnb feel more like an upscale executive suite in a luxury hotel! Both bedrooms boast attached bathrooms, the largest of which has a tiled shower & separate soaking tub!

Station House West: Upscale Condo in Cambridge, MD

Welcome to the Station House, a freshly renovated condo nestled in the heart of downtown Cambridge, Maryland, with its fabulous downtown pubs, galleries, and boutiques and close to the Harriet Tubman Center, Blackwater Wildlife Refuge, and Sailwinds Park. Located in the historic Four Corners building, the space offers the perfect blend of charm and modern comfort. The property is thoughtfully furnished and fully stocked to create a unique and comfortable home away from home.

Harbor Hangout • Boat Days + Family Nights

Welcome to Harbor Hangout! Freshly renovated 4BR/4.5BA condo in West Ocean City, Maryland - perfect for families and fishing crews! Walk to Ocean City Fisherman’s Marina for easy tournament days, then dine at Crab Alley, Sunset Grille, The Shark on the Harbor, or Harborside Bar & Grill. Minutes to beaches, Boardwalk, Assateague Island, plus events like White Marlin Open, Sunfest, and the Ocean City Air Show. Spacious, kid-friendly, and built for boat mornings + family nights.

Sunset Bay Villas 219 waterfront condo

Amazing views- Welcome Bird Watchers, Nature and Beach Lovers! Designer condo with direct views of the Intracoastal Waterway Chincoteague Channel and Wallops Long term rental from October-May with government per diem per person and special offers for long term occupancy. Max. occupancy per Chincoteague town fire code is 8. This includes adults, children (2 and older) and infants (children under two). Government ID issued required to be shown on or before check in date.

NEW! Entire Townhouse, Minutes from Downton OC!

Stop right there!! This 2-bedroom, 1.5 bathroom beautifully renovated in 2022 - entire townhouse w/ a private outdoor patio is the perfect space for your Ocean City vacation. You are less than a 5-minute drive to the beach & downtown Ocean City Inlet. Walking distance to OC's most famous local bars/restaurants; Sunset Grille, Brass Monkey, Crab Alley, Harborside, and Sunset Marina. Tanger Outlets are less than 1 mile away! Access to community pool and free parking!

Walk to Main St: Condo w/ Pool Access in Crisfield

Community Pool | Marina On-Site | Walk to Ferry Terminal Rest and relaxation await at this 3-bedroom, 2-bath vacation rental condo in Crisfield, Maryland. Enjoy the serenity of the morning with scenic water views of Daugherty Creek while sipping coffee on the private screened balcony. Then, peruse the local shops, hop on the ferry to explore Smith Island, or spend an afternoon lounging at Crisfield’s Wellington Beach. Your next getaway is just a click away!

It's 5 O'clock Somewhere|Stunning Waterfront Condo

Welcome to “It’s 5 o’clock Somewhere” on Marsh Island—your cozy retreat with panoramic views of Chincoteague and Black Narrows Channels. Perfect for 2 guests, this unit features a queen bed, full bath, kitchenette, Smart TV, and private sun porch. Enjoy shared amenities like a dock, grill, picnic table, and laundry. Relax, unwind, and take in the coastal beauty—just minutes from downtown Chincoteague. No pets. No smoking.