Condo vacation rentals in Crisfield

Ocean Pines Getaway with Marina View

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

Beautiful Bethany Bay Condo

Your home away from home... This beautiful, well-appointed condo is the perfect spot for a vacation getaway. Close enough to the action yet far enough away from the hustle and bustle, this condo is perfectly situated in Ocean View, Delaware on the Indian River Bay. Located in beautiful Bethany Bay, this community has amenities for the whole family such as a pool, 9-hole golf course, tennis, basketball courts & more. This unit offers a lovely view, but please note that there is no elevator.

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 Drinking Gourd: Stunning Cambridge Penthouse

The Drinking Gourd is a beautiful 2 bedroom, 1 bath penthouse located in the heart of the historic district of downtown Cambridge, MD. It features 15 foot ceilings, exposed brick, and original mahogany millwork throughout. The fantastic downtown pubs, galleries, museums, and boutiques are literally right outside the door, and the stunning Cambridge Marina is a short 4 blocks away. Cambridge has a wonderful food culture as well as local breweries and wine bars all within walking distance.

Eastern Shore Getaway: Bethany Bay

Fully furnished 2 Bed, 2 Bath condo near family friendly Bethany Beach, DE. Sleeps eight (one king, one queen sleeper, four twins). Refrigerator, washer/dryer, stove, dishwasher, toaster, Keurig coffee maker, Smart TVs, DVD, dishes, cookware. Sheets and towels provided. Guests bring food and toiletries. Community has tennis, pickleball, pool, playground, volleyball, basketball, small boat launch, and par 3 golf. 15 min to Bethany Beach, 35 min to Rehoboth. Great golf nearby.

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.

Bethany Beach Luxury Resort 2BR condo, 2nd floor

Your home-away-from-home features a covered patio and charming, beach-themed decor. The 2-bedroom, 2-bathroom space is located at the Bethany Bay Golf Resort and boasts fantastic amenities including a golf course, tennis and pickleball courts, a marina where guests can launch kayaks, a pool and hot tub, and more! Venture off the property and spend a day at the boardwalk, relax at the beach at Fenwick Island State Park, and sample local food! Close to the Freeman Arts Center.

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!

Bear Trap Dunes Condo - Perfect Location w/ Porch!

NEWLY RENOVATED FOR THE 2025 SEASON This lovely condo is located in the Village at Bear Trap Dunes just steps away from the golf course, clubhouse, pool, tennis, and fitness center. This condo offers a spacious living room and kitchen, 2 bedrooms, 2 full bathrooms (with a shower and tub in both), and a great screened-in porch and open-air deck to relax after a long day on the links, beach, or activities. Come enjoy our place with your friends and family!