Condo holiday rentals in Crisfield

Signature Retreat at The Peninsula | Newly Release

Important scheduling note: From Memorial Day through Labor Day, this home operates on a Saturday-to-Saturday schedule with a 7-night minimum stay. Peak-season availability is limited and typically reserved well in advance. Positioned within the gated Peninsula on Indian River Bay, this premier Signature Home is curated for guests who seek a refined coastal experience—where quality, comfort, and setting are thoughtfully aligned. With two private bedrooms and two full baths, the residence is ideally suited for couples, small families, and extended stays that benefit from both elegance and ease. The interior is calm, polished, and intentionally designed. An open, well-balanced layout allows natural light to move easily through the space, creating an environment that feels welcoming from the moment you arrive. Living and dining areas are arranged for relaxed gatherings and unhurried evenings, while the bedrooms are set apart to provide privacy and truly restorative rest. The kitchen is fully equipped for everyday use, supporting everything from casual breakfasts to longer stays without compromise. Elevator access within the building adds a level of convenience that guests appreciate, particularly for multi-week visits or arrivals with luggage. This is not a high-turnover rental. It is a professionally managed Signature Home, prepared to elevated standards and offered within a highly sought-after community where demand consistently exceeds supply. Comparable residences within The Peninsula that allow full guest access and meet this level of care are limited. Guests who recognize the fit tend to secure their dates early, as availability—especially during peak summer and golf season—does not remain open for long. Need to Know: Hotel-quality linens and bath towels are professionally provided for the home based on registered occupancy levels, ensuring the residence is properly prepared for your stay. Secure, keyless entry is provided, with a personalized door code issued prior to arrival for a smooth and private check-in experience. Parking accommodations include one reserved, covered space located beneath the building and clearly marked with the unit number. Additional vehicles may park in designated community parking areas. Gated community arrival: Guests are required to stop at the security gate upon entry to check in and receive access authorization. HOA operations notice: Community amenities are restricted on Saturdays due to scheduled turnover. This policy is established by the HOA and applies without exception.

Le Petit Paradis-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.

A Kozy Waterfront Condo

From the balcony of this "Kozy Waterfront Condo", enjoy relaxing sunsets overlooking the "Deep Harbour Marina" and a birds-eye-view of the Choptank River Lighthouse. The condo is in a gated community and close to most of what Cambridge has to offer. Downtown historic Cambridge and the Dorchester County Visitor Center are 1/4 mile away. A favorite of tourists, downtown Cambridge offers a variety of fun activities such as free concerts, festivals, restaurants, and an array of local shops.

Another Day in Paradise

ANOTHER DAY IN PARADISE CHINCOTEAGUE - Sunset Bay Villas #103 Owner Operated by: Annie Switzer Unit 103 has hardwood floors, granite counter tops, beautiful decor, and amazing water views! This first floor condo in Sunset Bay is located in a private corner of the community. It is professionally decorated with a relaxing, spa-like feel and an open layout in the main living area. There is a wall mounted gel fuel fireplace and a great private deck with a spectacular bay view.

Waterfront Chincoteague Island

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.

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!

The Tarryn Elizabeth Unit A

What better way to enjoy a getaway or family vacation than on a peaceful quiet island where the beach is clean and spacious and some of best fishing and crabbing in the world! Rent a four wheeler and drive on the beach 24/7 or lounge on the porch and soak in the sun, and not to mention the unlimited hi speed Internet with smart TVs in all 3 rooms for all your relaxing needs if you should choose to stay in the home!

Sunrise Sonata by Seaside Vacations & Sales

Sunrise Sonata is a fabulous 1st Floor Waterfront Vacation Rental on Chincoteague Island. This adorable Condo sleeps 4 and is located directly on the Assateague Channel, where the famous Chincoteague Pony Swim happens each year!

Assateague Inn 213 by Seaside Vacations & Sales

Relax and unwind at The Assateague Inn on Chincoteague Island. Assateague Inn 213-2R is an adorable Double Studio with 2 adjoining rooms that sleeps 4 with lovely water views and an Outdoor Pool.

Assateague Inn 204 by Seaside Vacations & Sales

Relax and unwind at The Assateague Inn on Chincoteague Island. Assateague Inn 204 is an adorable Studio that sleeps 4 with lovely water views and an Outdoor Pool.

Wharfside Suites Condo

Spacious condo located in the heart of downtown Chincoteague Island, VA. All linens, dishes and amenities are included and you are just minutes from the beach.