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. June's Retreat

    One of Chincoteague's Finest Estate Homes

    June’s Retreat is Chincoteague Island’s premier luxury vacation rental home, nestled on serene waterfront marshlands just north of town off of Main Street. This custom designed and decorated home leaves no detail unnoticed. From the bright spacious rooms with floor-to-ceiling windows to the expansive wrap-around verandas, you’ll feel as though you’re one with nature and your surroundings. Downstairs features a chef’s quality kitchen, private billiards room, waterside glass atrium, living room, private den, formal dining room, sitting room and a bathroom. Upstairs you’ll find 4 bedrooms with bathrooms (en suite), a sitting area and balcony. The panoramic views of Chincoteague Bay are unobstructed and unsurpassed. Come and see for yourself; we promise you won’t be disappointed! Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 12
    • 4 beds, 5 bathrooms
    • View Details
    June's Retreat
    5389 Main Street
    Chincoteague Island VA
    37.9522546, -75.3493612
  2. Blue Pointe Bayside

    Bayfront Luxury & Amazing Sunsets

    Spectacular waterfront home on the end of a cul-de-sac! Bright, airy and immaculate! Four decks, (one off of the stunning 2nd floor - Private Master Suite). Dramatic cathedral ceiling in the cozy, waterfront living room. A screened porch to host an outdoor dinner. Central heat, a fireplace (pellet stove) and Central A/C makes this the perfect vacation house all year. A sunny, well equipped, eat in kitchen for the gourmet cook. Down-Draft cook top and gas grill perfect for any meal. Beautiful sunsets on the Chincoteague Bay. Water views from every room! Detached game room and TV/Playstation area with 2 sleeper sofas and full bath! Large, hot water outside shower and an oyster shell path to the water so you can easily walk out to the bay to crab, fish and kayak. Internet Service! Beach and fishing/crabbing supplies provided. Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 8
    • 3 beds, 3 bathrooms
    • View Details
    Blue Pointe Bayside
    5038 Bay Colony
    Chincoteague Island VA
    37.9529158, -75.352438
  3. Gone Coastal

    Beachy Getaway with Master Suite

    Tastefully remodeled and decorated, 'Gone Coastal' is the perfect motto for this beach getaway! Located close to downtown - movies, shopping, restaurants and more. And you're only about 2 miles to the entrance to the beach! This rental features all modern amenities (central a/c & all appliances) and comfortable furnishings. There's an open balcony out front, and a screened in grilling deck out back. The master bedroom suite upstairs features it's own private screened porch. Loaded with extras; you won't be disappointed! Note: No boats or trailers are allowed at the complex. Read more »
    • Chincoteague Island
    • In Town
    • Townhouse
    • Sleeps 8
    • 2 beds, 2.5 bathrooms
    • View Details
    Gone Coastal
    4410 Eastwinds
    Chincoteague Island VA
    37.9264464, -75.3650442
  4. Conch Shell

    Beach Bungalow - Bring Your Kayak!

    The house is located on Pine Drive on Piney Island, closest neighborhood to the beach and convenient for shopping and dining on Maddox Blvd. This wonderful waterfront beach bungalow features a wrap around deck with views of Assateague and the light house. You can bring your boat, jet skis or kayaks and keep them tied up out front. There is a spacious living room for entertaining and a nicely remodeled kitchen! Your rental also includes water access (a short walk from the home) to a tidal creek that comes up from Oyster Bay - it's a great place for the kids to crab or to launch a kayak or canoe. Read more »
    • Chincoteague Island
    • Piney Island
    • Single Residence
    • Sleeps 7
    • 3 beds, 1 bathrooms
    • View Details
    Conch Shell
    7143 Pine Drive
    Chincoteague Island VA
    37.9237753, -75.3505016
  5. 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! This unit 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
  6. Heron's Cove On Salt Meadow

    Secluded Waterfront with GREAT Amenities!

    Peaceful and stunning waterfront home! Located on a quiet side-street, Heron's Cove features a reverse floor plan with all bedrooms on the first floor, and the main living-level on the second floor. This allows you to capture and maximize the fabulous bay views! The second floor also features a great room with cathedral ceilings, fully equipped kitchen, gas fireplace and screened gazebo. In addition, there's multiple open decks and a shared dock into Little Oyster Bay. There are three bedrooms that each have a king size bed, and one bedroom that has two sets of bunk beds. Each bedroom has a private bath. Luxurious comfort while surrounded by Chincoteague's natural beauty and wildlife! Read more »
    • Chincoteague Island
    • Oyster Bay
    • Single Residence
    • Sleeps 10
    • 4 beds, 5 bathrooms
    • View Details
    Heron's Cove On Salt Meadow
    6289 Hancock Lane
    Chincoteague Island VA
    37.9329542, -75.3545377
  7. Catch Of The Day

    Great Vacation Home

    Catch of the Day is very comfortable and affordable duplex home that will cater to all of your vacation needs. This can be your home away from home - near the beach! The first level offers a large living room, a bedroom (D), an eat-in kitchen, 1/2 bath and very nice screened porch. There are two bedrooms on the second floor, one with a queen bed and the second with two twins, and there is a full bathroom. Read more »
    • Chincoteague Island
    • In Town
    • Duplex
    • Sleeps 6
    • 3 beds, 1.5 bathrooms
    • View Details
    Catch Of The Day
    6005 Hill Lane
    Chincoteague Island VA
    37.9393363, -75.3487093
  8. Cockleshell Cottage

    1st Floor Master & Pet Friendly!

    Nestled on a quiet cul-de-sac in a private community just off North Main Street (Oyster Bay II) is where you'll find the charming Cockleshell Cottage! This modern 3 bedroom, 3 bathroom home boasts a first-floor master bedroom suite (Queen), all amenities and comfortable furnishings. Upstairs features 2 more bedrooms (Double and Double/pull-out Twin trundle), and a full bathroom. Cockleshell Cottage is handicap accessible. Relax and enjoy the breeze on the open front porch or back screened porch. Call us today; this home books fast! NO SMOKING, PET FRIENDLY with restrictions. Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 10
    • 3 beds, 3 bathrooms
    • View Details
    Cockleshell Cottage
    5146 Deep Fern Court
    Chincoteague Island VA
    37.949885, -75.351645
  9. Joint Venture

    Great Fun Spots Nearby - Bike to Beach!

    Joint Venture is the perfect townhouse for an affordable vacation! Take a short stroll or bike ride to ice cream, mini golf or any of the shops on Maddox Blvd. Bike or drive to the beach from the property! Joint Venture offers a water view of Little Oyster Bay (tidal creek) that can be enjoyed any time of year. This property offers Wi-Fi and is pet friendly! Don't miss out! Read more »
    • Chincoteague Island
    • In Town
    • Townhouse
    • Sleeps 6
    • 2 beds, 2.5 bathrooms
    • View Details
    Joint Venture
    6388 Teal Lane #9
    Chincoteague Island VA
    37.9313574, -75.3590104
  10. Coastal Breeze

    Amazing Decks & Bay Views!

    Coastal Breeze is a modern 3 bedroom, 2 bathroom single-family home located just off of North Main Street. You know as soon as you walk into this house that you are at the beach. There are tiled floors throughout the entire house with the exception of carpet in the bedrooms. The first floor offers 2 bedrooms (1K and 1Q), 2 full bathrooms, sitting area with a sleep sofa, and a large deck. The second floor boasts an open floor plan with a screened porch and open deck off of the living room with views of the Chincoteague Bay. There is an additional bedroom on the second floor with a trundle bed (2T). There is a TV in the living room and a TV in the master bedroom. Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 8
    • 3 beds, 2 bathrooms
    • View Details
    Coastal Breeze
    5061 Bay Colony Lane
    Chincoteague Island VA
    37.9529532, -75.3510683
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800-668-7836 | rentals@chincoteagueresort.com | http://www.chincoteagueresort.com | 6426 Maddox Blvd, Chincoteague Island, VA 23336