WELCOME TO OUR ON-LINE AVAILABILITY & BOOKING SERVICE!

Search for your perfect rental & book it on-line with your credit card. IT'S THAT EASY!!

IMPORTANT SEARCH GUIDELINES:
1. If searching by Arrival Date, you must enter a Friday, Saturday or Sunday date. Each day will show different results.

2. When selecting your Length of Stay, you must select in increments of 7 nights during the in season (Memorial Day - Labor Day). You may select any length of stay during the off season.

Availability is updated in real-time, so it is the most current information we have. Once you have completed your reservation, a Guest Rental Agreement (signature required) and Reservation Confirmation will be emailed to you. We look forward to hosting your Chincoteague Island vacation!

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  1. Sea Charm

    In Town Location and Fenced Yard

    Charming in-town 3 bedroom home with a day-bed alcove, 2 baths, large fenced yard, carport and screened porch. Located on a quiet street, but a short walk to downtown shopping, movies and restaurants. Expanded Master Bedroom with claw foot tub and king size bed. Amenities also include outside (hot/cold water) shower and 2 TVs. Please Note: Linens and/or towels are optional and can be provided upon your arrival - please inquire about our linen packages. This property is NO SMOKING & NO PETS. Read more »
    • Chincoteague Island
    • In Town
    • Single Residence
    • Sleeps 8
    • 3 beds, 2 bathrooms
    • View Details
    Sea Charm
    6298 Mumford St
    Chincoteague Island VA
    37.9327186, -75.3752226
  2. Crossroads

    Waterfront * Sunset Views * Private Setting

    Peace and tranquility is what Crossroads (formerly known as Sunset Cove) offers. Totally re-done in 2019, this beautiful 4 bedroom waterfront home in the Smugglers Cove area is nestled on the northwestern shores of Chincoteague Island offering a world class view of Chincoteague Bay along with its own private peninsula, pristine woods and marsh. On the first level is a great room, with large waterfront windows, a stone fireplace and comfortable seating. A long family dining table and open, modern kitchen with island and counter seating opens to a breakfast area overlooking the bay. A master bedroom (King), with private deck access and en suite bath, and a powder room complete the floor. The second level has three more bedrooms (2 Queens/2 Twins) and leads to the third level bonus/entertainment room with water-view windows. Two decks and a screened porch wrap around half of the house, each with water and unsurpassed sunset views. The property’s own peninsula jutting into Chincoteague Bay offers complete privacy, a shallow water boat slip and awe-inspiring views. Note: This property has a 7 night minimum during all seasons. Linens and/or towels are optional and can be provided upon your arrival - please inquire about our linen packages. This property is NO SMOKING & NO PETS. Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 8
    • 4 beds, 2.5 bathrooms
    • View Details
    Crossroads
    4446 Shady Lane
    Chincoteague Island VA
    37.9539217, -75.3469762
  3. Avalon

    Oyster Bay I Community * Waterside Screened Porch

    Avalon is a charming 4 bedroom, 2.5 bathroom home situated on a bulkheaded waterfront lot on Oyster Bay! There is a large great room that boasts two family rooms, a dining area and large kitchen. From the gas fireplace, to the 16' cathedral knotted pine ceilings, this home is bright, warm and inviting. Avalon offers two queen bedrooms with screened porch access (one private) and two twin bedrooms. Offering over 600 sq. ft. of screened porch - you could live outdoors! The first level also offers a full size futon and 1/2 bath. Avalon is one of our most popular offerings; it books quickly! Please note: Linens and/or towels are optional and can be provided upon your arrival - please inquire about our linen packages. This property is NO SMOKING & NO PETS. Read more »
    • Chincoteague Island
    • Oyster Bay
    • Single Residence
    • Sleeps 10
    • 4 beds, 2.5 bathrooms
    • View Details
    Avalon
    5421 Hibiscus Court
    Chincoteague Island VA
    37.945001, -75.3502309
  4. Diving Duck

    Waterfront * Golf * Swimming * Fine Dining

    If you're looking for the complete vacation package, look no further! This 4 bedroom home features a spacious open floor plan with wall-to-wall sliding doors and windows, allowing natural light to permeate throughout the home. Downstairs you'll find the living room and great room with access to the waterside deck, a large dining area, kitchen with all the counter space you'd ever need, a half bathroom, and the master bedroom with private bath (with custom tile shower and soaking tub). Upstairs features a landing area with sofa and foosball table, 3 more bedrooms and another full bathroom. Under the house, you'll find the perfect spot for a game of ping pong. Aptly named, 'Diving Duck' is the perfect spot for watching the ducks and wildlife pitch in the bay just out the back door. There's even a floating dock perfect for launching canoes and kayaks! And as if all of that is not enough, the Captains Cove community features swimming pools (2 outdoor, 1 indoor), a fitness center, marina club restaurant and 9-hole golf course. (Small fee applies for usage of community amenities.) This rental home is approximately 20 minutes to Chincoteague/Assateague Island (the beach) and 30 minutes to Ocean City, MD (beach & boardwalk attractions). What more could you ask for? Book your stay at 'Diving Duck' today! Please note: Linens and/or towels are optional and can be provided upon your arrival - please inquire about our linen packages. This property is NO SMOKING & NO PETS. Read more »
    • Captain's Cove
    • Captain's Cove
    • Single Residence
    • Sleeps 15
    • 4 beds, 2.5 bathrooms
    • View Details
    Diving Duck
    3224 Salty Way
    Greenbackville VA
    37.9901597, -75.4154453
  5. Island Girl

    Bright, open floor plan * Contemporary Waterfront

    Spacious waterfront home with water views from every window! The Great Room includes comfortable living and dining areas and a modern, fully stocked kitchen w/ breakfast bar. Amenities include central heat & air, private outside shower, wood stove, grill, screened porch and lots of deck space! And there's a new dock for guests to be able to launch kayaks and canoes! Island Girl is the perfect spot for your beach vacation; you won't be disappointed! Please Note: Linens and/or towels are optional and can be provided upon your arrival - please inquire about our linen packages. This property is NO SMOKING & NO PETS. Note: The bed sizes are 3 queens and 4 twins. Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 10
    • 4 beds, 2 bathrooms
    • View Details
    Island Girl
    5498 Warren Street
    Chincoteague Island VA
    37.9525084, -75.3436886
  6. Sunset Bay Villa 212

    Beautiful Condo - Elevators, Pool, Fitness Room

    A waterside condo that offers you all of the comforts of the Sunset Bay Villas. Enjoy the community pool and fitness center! Located on the edge of beautiful Chincoteague Bay, Sunset Bay Villas are distinctive condominium homes that offer nothing less than the finest amenities. This unit boasts over 1,700 square feet of living space with 3 bedrooms. Spacious waterfront balcony, private master bedroom suite with tub and tile shower, open kitchen, and large rooms. Conveniently located to our historic downtown area, you can walk to dinner, movies, shopping, galleries & more. Please note: Linens and/or towels are optional and can be provided upon your arrival - please inquire about our linen packages. This property is NO SMOKING & PET FRIENDLY (with fee). This unit does not include a boat slip, however, use of the marina is included. Read more »
    • Chincoteague Island
    • Sunset Bay Villa
    • Condo
    • Sleeps 6
    • 3 beds, 2 bathrooms
    • View Details
    Sunset Bay Villa 212
    6321 Captain's Lane #212
    Chincoteague Island VA
    37.9322012, -75.380982
  7. Grandview

    Luxury Bayfront Home with Dock! Pet Friendly!

    Enjoy stunning sunsets from this 5 star home at water's edge. Relax with the amazing water view from the north side of the island. Every bedroom is a suite, to ensure all of the adults have the right amount of privacy and a quiet place to stow away with a book. The dining area is big enough to accommodate large family dinners and the kitchen has been newly remodeled and upgraded! With a breakfast bar and wide open living area, you can be sure to have lasting family moments together. Have your cameras ready to capture the changing tides, wildlife and those crazy family moments that are sure to happen in this lovely home. Grandview offers every amenity from a screened porch, an open deck, long pier with a dock, ceiling fans throughout, wireless internet and much much more! This home also includes the use of 2 bicycles and 2 kayaks. Please Note: Linens and/or towels are optional and can be provided upon your arrival - please inquire about our linen packages. This property is NO SMOKING & PET FRIENDLY (with fee). Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 10
    • 4 beds, 4 bathrooms
    • View Details
    Grandview
    5064 Wildcat Lane
    Chincoteague Island VA
    37.9618304, -75.3381306
  8. Moments in the Mist

    Pet Friendly * Just Blocks from the Beach * Quaint Seaside Community

    Welcome to "Moments in the Mist" located in the historically-rich town of Cape Charles on the Eastern Shore of VA! As one of our newest vacation home offerings, we know you'll be delighted by the coastal-chic decor and furnishings in this newly remodeled home. The location is ideal for most - "Moments in the Mist" is located on a quiet residential street just far enough from town that you can enjoy the peace and quiet, but close enough that you're just a few blocks from the beach and downtown area. As you enter this fabulous vacation home, the first floor features an open air country-style front porch (perfect for sitting with coffee or a cool drink!), the living room with a new flat-screen smart TV (for streaming your favorite shows), a dining room with a table big enough for the whole family, a spacious kitchen with additional high-top seating area, and a sliding door that leads out to the expansive back deck and back yard. There's plenty of outdoor space here! The downstairs also features a new 1/2 bath (powder room). The second floor features 3 bedrooms and a new full bathroom with a beautifully tiled shower (no tub). And, to complete the full vacation package, this rental includes the use of a golf cart for conveniently scooting around town and to the beach! Bring your furry family members along; "Moments in the Mist" is pet friendly! The quaint, beach town of Cape Charles features a beautiful beach, theater, library, golf cart & bike rentals, fishing charters and a variety of restaurants & shops (even a local brewery and distillery!). It's just 3 miles from one of the Modern Wonders of the World - The Chesapeake Bay Bridge Tunnel! The location makes it easy for day trips to Busch Gardens in Colonial Williamsburg, or Ocean Breeze Fun Park in Virginia Beach! Please note: Linens and towels are included with your reservation. This rental home is NO SMOKING and PET FRIENDLY (with additional fee). Read more »
    • Cape Charles
    • Cape Charles
    • Single Residence
    • Sleeps 6
    • 3 beds, 1.5 bathrooms
    • View Details
    Moments in the Mist
    635 Jefferson Avenue
    Cape Charles VA
    37.2723421, -76.0112875
  9. Sunset Bay Villa 312

    Beautiful Condo - Elevators, Pool, Fitness Room

    Villa 312 is a beautiful 3 bedroom villa featuring a master bedroom suite with luxury bath, gourmet kitchen with center island which is great for entertaining, laundry room with washer/dryer and a waterside balcony overlooking Chincoteague Bay. There are tvs in all the bedrooms, and a computer desk to work from. Villa 312 will sleep 8, and features lots of extras including beach gear and baby gear for your use, as well as a 14' boat slip. Your rental also includes the use of the Sunset Bay pool and fitness area. Located adjacent to our historic downtown area, where you'll find gourmet food shops, boutiques, a public library, galleries and fine dining - all with a short stroll. Come and enjoy a Sunset Bay vacation! Note: This villa has access to a 14' boat slip. Linens and/or towels are optional and can be provided upon your arrival - please inquire about our linen packages. This property is NO SMOKING & NO PETS. Read more »
    • Chincoteague Island
    • Sunset Bay Villa
    • Condo
    • Sleeps 8
    • 3 beds, 2 bathrooms
    • View Details
    Sunset Bay Villa 312
    6321 Captain's Lane #312
    Chincoteague Island VA
    37.9327866, -75.3813864
  10. My Island Escape

    New construction * Shared Dock * Immaculate!

    Tucked away on a quiet lane off of North Main is where you will find My Island Escape. This brand-new home is absolutely immaculate! Luxury finishings, tastefully appointed furniture and décor make for a flawless backdrop to your next vacation. The living room at My Island Escape features ample comfortable seating and a flat screen television, and flows into the fully equipped, gourmet, eat-in kitchen that features a large island and plenty of space for cooking, dining, and enjoying meals with the family. The master bedroom features a Queen size bed with an en suite highlighted by a large soaking tub, double vanity, and separate glass stand up shower. The two other bedrooms in the home are close by a full bathroom located off the hallway. Another bonus in this home is the spacious laundry room complete with a full-size washer and dryer, iron and an ironing board, and connects to a convenient half bath. Outside, you will find deck space with outdoor furniture, and a picnic table with umbrella for outdoor dining. If you are looking for a clean, relaxing, upscale rental with great attention to detail – look no further and escape to My Island Escape! Please Note: Linens and/or towels are optional and can be provided upon your arrival - please inquire about our linen packages. This property is NO SMOKING & NO PETS. This rental features shared dock access. Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 7
    • 3 beds, 2 bathrooms
    • View Details
    My Island Escape
    5061 Demarco Lane
    Chincoteague Island VA
    37.9513169, -75.3518393
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800-668-7836 | rentals@chincoteagueresort.com | http://www.chincoteagueresort.com | 6426 Maddox Blvd, Chincoteague Island, VA 23336