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. Southern Exposure

    Most Beautiful Views Deep Water Pier

    Southern Exposure is nestled along the natural shoreline of the Assateague Channel, offering some of the most beautiful water views on Chincoteague Island. Conveniently located in one of Chincoteague's most popular residential communities, you're only minutes from the beach and attractions - shopping, mini golf, restaurants and more! This ranch-style home features 4 bedrooms, and all your main living areas, on one level. Enjoy relaxing moments on the waterside screened porch or private deck overlooking the marsh and Assateague Channel. And you can crab/fish, kayak or dock your boat from the deep-water pier (with ladder and floating dock). It doesn't get much better than this! Read more »
    • Chincoteague Island
    • Piney Island
    • Single Residence
    • Sleeps 8
    • 4 beds, 2 bathrooms
    • View Details
    Southern Exposure
    7005 Pine Drive
    Chincoteague Island VA
    37.9260535, -75.345926
  2. Stingray

    Very Nice Condo Overlooking Lighthouse

    Luxurious 2nd-level waterfront condo with views you won't believe! Tastefully decorated with work of local artisans, features all amenities, as well as master bedroom suite with king bed & waterside balcony. Many extras like a flat screen TV and a Lazy Boy leather recliner. The open floor plan is great and features a breakfast bar between the kitchen & dining area! NOTE: Parking and dock restrictions apply. No smoking/No pets. Read more »
    • Chincoteague Island
    • Eastside
    • Condo
    • Sleeps 6
    • 2 beds, 2 bathrooms
    • View Details
    Stingray
    7622 East Side Drive #205
    Chincoteague Island VA
    37.9182314, -75.3717214
  3. Morning Song

    One Of Our Favorite Rentals!

    Nestled on the edge of Assateague Bay and overlooking the wild salt marshes of Assateague and Morris Islands is where you'll find this gem. With capacity for 10 guests, the 4 bedroom 3 bath contemporary ranch home features a pier and dock on deep water, screened porch and open deck area, a widow's walk, 2 fireplaces, a fully stocked kitchen including dishwasher, central heat and air and washer dryer. The open floor plan features bedroom suites on all sides making Morning Song a beautiful place to spend your summer vacation. Home has ramp access. Internet access provided. Read more »
    • Chincoteague Island
    • Oyster Bay
    • Single Residence
    • Sleeps 10
    • 4 beds, 3 bathrooms
    • View Details
    Morning Song
    5440 Deep Hole Road
    Chincoteague Island VA
    37.939142, -75.34735
  4. Admiral Benbow

    Fish & Crab at the Community Harbor!

    A very nice contemporary home located in Oyster Bay I. Located next to the community boat ramp - you have access to the water and the kids can fish and crab from the dock areas. This house has an outdoor ramp to the ground level. Don't miss out on the great screened porch for a family dinner. Bed sizes allow the perfect set up for families of all ages! Read more »
    • Chincoteague Island
    • Oyster Bay
    • Single Residence
    • Sleeps 8
    • 3 beds, 2.5 bathrooms
    • View Details
    Admiral Benbow
    5426 Pearl Drive
    Chincoteague Island VA
    37.9433329, -75.3476952
  5. 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 new 3 bedroom, 3 bathroom home boasts a first-floor master bedroom suite, all modern amenities and new furnishings. It is handlcap 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 8
    • 3 beds, 3 bathrooms
    • View Details
    Cockleshell Cottage
    5146 Deep Fern Court
    Chincoteague Island VA
    37.949885, -75.351645
  6. An Unfettered View

    Secluded Scenic Waterfront Retreat

    This beautiful 2BR ranch home has a quiet, out-of-the-way location on little Oyster Bay. The views of the bay are beautiful and expansive with a long pier straight from the back deck its perfect for crabbing, kayaking & canoeing. An Unfettered View features all amenities including a private master suite with full bath, central air, all appliances including dishwasher, washer/dryer, wireless internet service and a wonderful family room on the waterside of the home. Tastefully furnished and very accommodating, this is a great home. An Unfettered View is a wheelchair accessible home. Read more »
    • Chincoteague Island
    • In Town
    • Single Residence
    • Sleeps 8
    • 2 beds, 2 bathrooms
    • View Details
    An Unfettered View
    6254 Wagner Lane
    Chincoteague Island VA
    37.9337339, -75.3529337
  7. Ocean View Retreat

    5 Bedroom Waterfront with Boat Launch!

    Nestled on the eastern tip of Chincoteague Island, this spacious waterfront estate has been designed and meticulously constructed by a local craftsman. Enjoy the unobstructed views of Assateague Channel and the lighthouse while the sounds of nature delight your senses. Features include 5 bedrooms, a private suite downstairs and a large den/bonus room, all with TVs (including a master suite with private bathroom), 3 full bathrooms & 1 half bathroom, living room, formal dining room and ktichen with all appliances including a TV, expansive decks, large dock and private boat slip, widow's tower and and wireless internet. No details were spared in this 4,000 square foot beach retreat. You'll enjoy the quiet location and panoramic water views from every room. No smoking; no pets. Read more »
    • Chincoteague Island
    • Eastside
    • Single Residence
    • Sleeps 14
    • 5 beds, 3.5 bathrooms
    • View Details
    Ocean View Retreat
    7159 Sheepshead Lane
    Chincoteague Island VA
    37.9225272, -75.3619982
  8. Panorama

    Dock for Fishing and Crabbing

    Tastefully appointed first-floor condo situated on the Assateague Channel. Enjoy the unobstructed views of the channel and Assateague Lighthouse! Master bedroom suite with doors to waterside deck area, screened porch, open floor plan and more. Recently updated and refreshed, this is a great unit! NOTE: 2 parking spaces only. Boats, kayaks, canoes, and trailers of any kind are not permitted in the parking lot of this unit. Dock restrictions apply. Read more »
    • Chincoteague Island
    • Eastside
    • Condo
    • Sleeps 6
    • 2 beds, 2 bathrooms
    • View Details
    Panorama
    7622 East Side Drive #103
    Chincoteague Island VA
    37.9182314, -75.3717214
  9. Lighthouse Pointe

    AMAZING WILDLIFE right outside your door

    One of East Side's most popular rentals! Features include open floor plan with waterside balcony downstairs, and a spacious third level master bedroom suite with private waterside balcony. All levels have balconies or a deck! Very conveniently located - close to Memorial Park, restaurants and marina. Don't wait on this one, it rents quickly! Shared dock area for boat dockage, max. boat length 20 ft. Read more »
    • Chincoteague Island
    • Eastside
    • Townhouse
    • Sleeps 8
    • 3 beds, 2.5 bathrooms
    • View Details
    Lighthouse Pointe
    7718 East Side Road
    Chincoteague Island VA
    37.9199476, -75.3687755
  10. A Second Wind

    Modern & Magnificent * Beautiful Sunsets

    A luxury waterfront vacation rental home with community pool privileges. Located on Chincoteague Bay, right at the water's edge. Enjoy breathtaking views and beautiful sunsets! On the first floor you'll find a sitting area (Double-size pull out sofa), two bedrooms (Queen & 2 Twins) with a common full bath. There is deck access from the 1st floor foyer and bedroom overlooking the Chincoteague Bay. The second level features a large and bright open floor plan with yet another waterfront deck. The kitchen is equipped with beautiful granite counters, stainless steel appliances, breakfast bar, and everything else you'll need for your family meals. There's also laundry and powder room on the second level. The third floor is entirely a large master suite featuring a king bed, picture windows overlooking the bay, as well as a private balcony. Enter the master bath through french doors where you'll find a large Jacuzzi tub, double vanity and walk in shower. Enjoy a spectacular vacation at A Second Wind! Read more »
    • Chincoteague Island
    • South Main
    • Townhouse
    • Sleeps 8
    • 3 beds, 2.5 bathrooms
    • View Details
    A Second Wind
    3645 Main Street
    Chincoteague Island VA
    37.9273439, -75.3859178
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800-668-7836 | rentals@chincoteagueresort.com | http://www.chincoteagueresort.com | 6426 Maddox Blvd, Chincoteague Island, VA 23336