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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. Poole's Cove

    Bayfront Home Tucked Out of the Way

    Poole's Cove manages to be tucked away right on Main Street. This home has been decorated with an artists' eye and poet's heart. The set up of this home offers plenty of room for the whole family, but enough distance for quiet moments to yourself. The Master bedroom suite is located in the main part of the house. Just a few steps through a breezeway brings you to the second part of the home with 2 more bedrooms and bathrooms. The outside stairs will bring you up to a rooftop lounging area to catch some relaxing rays. Also upstairs is an office with the perfect reading nook to curl up and catch up on some reading. This house doesn't just offer you a stay it offers you the full experience. **IMPORTANT NOTE: Because of this home's unique floor plan and railing-less decks, it may not be suitable for younger children.** Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 6
    • 3 beds, 3 bathrooms
    • View Details
    Poole's Cove
    5019 Main Street
    Chincoteague Island VA
    37.9472472, -75.3580802
  2. Cove's Point

    Prime Waterfront Location * Pool * Boat Dock * Golf

    *Brand New Listing!* As one of our finest selections, we're pleased to be able to offer you this fabulous waterfront retreat - "Cove's Point"! Aptly named, this home is situated at Cockle Point and offers over 200 degree views of the Chincoteague and Horntown Bays. Enjoy the sunrise and sunset - the best of both worlds! The floor plan was strategically designed to take advantage of the location and capture unobstructed water views from every room. Enjoy the bright, open spaces with expansive windows. On the first floor you'll find the main living areas, including a sunroom, and a master bedroom suite with bathroom. The second floor features two more bedrooms and another full bathroom. Enjoy the coastal breezes from any of the 3 decks/balconies and 4 flat screen TV's with WiFi. Bring your boat - there's a private deep water pier that extends into the bay with a boat lift. Cove's Point is now PET FRIENDLY! In addition to all the fine features of this vacation home, you'll also enjoy all the community amenities that Captain's Cove has to offer! This includes 3 pools (2 outdoor & 1 indoor), tiki bar, fitness center, waterfront restaurant and marina club, boat launch, 9-hole golf course, kid's playground and so much more - all just minutes from the home! Read more »
    • Captain's Cove
    • Captain's Cove
    • Single Residence
    • Sleeps 10
    • 3 beds, 2.5 bathrooms
    • View Details
    Cove's Point
    37548 Bayside Drive
    Greenbackville VA
    37.9871732, -75.4095482
  3. A Sunshine Cottage

    Charming Chincoteague-Close to Downtown

    As one of our newest vacation rental listings, we're pleased to be able to offer you "A Sunshine Cottage"! With all the charm of a Chincoteague-style cottage, you'll be reminded of the days gone by. The front porch is the perfect spot to relax with a cool drink and book, and the convenient in-town location means you can stroll downtown after a day at the beach. Read more »
    • Chincoteague Island
    • In Town
    • Single Residence
    • Sleeps 4
    • 2 beds, 1 bathrooms
    • View Details
    A Sunshine Cottage
    6336 Jester Street
    Chincoteague Island VA
    37.9314724, -75.3795889
  4. Cozy View

    A true architectural delight, "Cozy View" is one of Chincoteague Island's unique gems. Conveniently located on North Main Street, this cottage is close enough to town, yet just far enough away to offer some peace and quiet. The stunning water views of the Chincoteague Bay and million-dollar sunsets are sure to please the senses. The main living level features a fabulous screened porch (perfect for lounging after a day at the beach or dining al fresco), the living room and a dining area (with drop-leaf table), kitchen, bedroom (two twin beds) and a full bathroom with tub and shower. The entire upstairs is a private master bedroom with en suite bathroom and access to the second-level sundeck. "Cozy View" was strategically and thoughtfully designed so that each room captures panoramic views of Chincoteague Bay. Come and enjoy a wonderful vacation at this comfortable and cozy escape! NOTE: This home will accomodate up to 5 guests with a queen bed, two twin beds, and a sofa in the living room (sofa is not a pull-out sleeper sofa). Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 5
    • 2 beds, 2 bathrooms
    • View Details
    Cozy View
    5052 Main Street
    Chincoteague Island VA
    37.946288, -75.3592654
  5. Wildflower

    Long Pier for Boating, Fishing and Crabbing,

    Beautiful waterfront home with shared pier plus floating dock on deep water!! Ground level is a large screened patio perfect for those summer time seafood feasts. The first level is great room boasting reclaimed barn board walls and wide plank pine floors with a separate den and full bath. There is a second screened porch overlooking that water from the great room. The second level has a large waterfront master suite with a private balcony, two more bedrooms and another full bath. Close to Memorial Park right across the street from a family restaurant! (Spiral staircase in home, may not be suitable for small children.) For larger groups for family reunions, check out nearby Moon Rising or Herbie's Hideaway! Read more »
    • Chincoteague Island
    • South Ridge
    • Single Residence
    • Sleeps 6
    • 3 beds, 3 bathrooms
    • View Details
    Wildflower
    7381 Hickman Lane
    Chincoteague Island VA
    37.9161709, -75.3852815
  6. Homestead

    Step Back In Time, Surrounded by Nature

    Set back across the street from Chincoteague Bay, Homestead sits on 5 acres and is a cozy 1890 cottage with the charm of yesterday and the comfort of today. Private, quiet, lots of room outside; it’s perfect for a retreat or family fun. Homestead sleeps 5 but is best suited for no more than 4 adults. A tidal pond in front, unspoiled woods in back make for your own nature preserve. How many different animals can you spot? *Brand new this year - The Homestead features a truly spectacular new addition of an open-concept family room, gourmet kitchen and dining area! This new area of the home was designed to preserve the natural landscape and capture all of nature's views - enjoy the natural lighting from over-sized windows and sliding doors, as well as skylights. A wall-mounted TV and fireplace complete the package!* Amenities that include bikes, beach chairs and umbrellas; games, crayons and colored paper; good parking and even herbs in the garden. Sit on the screen porch, feel the breeze from the bay or take an outside shower under the stars. As part of the property, you’ll vacation alongside the oldest home on the island, Captain Timothy Hill House, listed on The National Register of Historic Places. NEW FOR 2019: Homestead is undergoing a major renovation! Enjoy an additional full bathroom (2 total), a new kitchen/dining area, great room with gas fireplace, and 2 screened-in porches! The Homestead you've come to know and love will now be even better! Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 5
    • 3 beds, 2 bathrooms
    • View Details
    Homestead
    5122 Main Street
    Chincoteague Island VA
    37.9475987, -75.3572416
  7. Sunset Bay Villa 114

    Beautiful Condo - Elevators, Pool, Fitness Room

    Villa 114 is a beautiful, professionally decorated unit located close to the pool and fitness area. Spacious, light and bright, this ground-level unit features a private deck area with walk-out to the marina. The master bedroom has a private luxury bath with jetted tub and tiled shower; the gourmet kitchen will delight your senses; the center island entertaining bar is perfect for mixing drinks, and of course, the water views at sunset are breathtaking. Villa 114 will sleep 8; two of the three bedrooms have flat screen tvs, internet access, ipod docking and more. Treat yourself this year with a Sunset Bay vacation. Note: This unit does not have a boat slip. Read more »
    • Chincoteague Island
    • Sunset Bay Villa
    • Condo
    • Sleeps 8
    • 3 beds, 2 bathrooms
    • View Details
    Sunset Bay Villa 114
    6321 Captain's Lane #114
    Chincoteague Island VA
    37.9322012, -75.380982
  8. First Time

    Public Boat Launch Nearby!

    Fantastic 2 bedroom ranch-style home with a great location on East Side! This home features central air, washer/dryer, dishwasher, fireplace and more. Public boat launch located right across the street. Marina, Memorial Park and a seafood restaurant are all within a short distance. Large yard, deck, and covered outdoor area complete the package! Read more »
    • Chincoteague Island
    • Eastside
    • Single Residence
    • Sleeps 7
    • 2 beds, 2 bathrooms
    • View Details
    First Time
    7312 Turlington Lane
    Chincoteague Island VA
    37.9181764, -75.3725933
  9. Mallard's Walk

    Great Home Bring Your Kayak

    Enjoy the wonderful bay breezes from this charming waterfront home. Three bedrooms, great spacious kitchen, quiet porch to relax on and your own private pier/dock on Assateague Channel. Watch our world famous Chincoteague wild ponies grazing in the salt marshes of Assateague Island. No smoking and No pets. Wireless Internet and a fully enclosed outside shower with foot wash! NOTE: This rental features a large front yard, and the dock/waterfront access is across Eastside Road. Private pier. Read more »
    • Chincoteague Island
    • Eastside
    • Single Residence
    • Sleeps 6
    • 3 beds, 1 bathrooms
    • View Details
    Mallard's Walk
    7259 Mcgee Lane
    Chincoteague Island VA
    37.9194005, -75.3705005
  10. Sunset Bay Villa 116

    Beautiful Condo - Elevators, Pool, Fitness Room

    A beautiful ground-floor villa with walk out to marina. Luxurious master bedroom with private bath includes both a roomy tiled shower and whirlpool bath. Villa 116 will sleep 8 (beds for 6 plus a queen size air mattress), and includes a full laundry, all appliances, a gourmet kitchen, and more. There's also a pool and fitness room for your enjoyment! Tastefully furnished, you can relax, enjoy and entertain your family and friends in style. NOTE: This unit does not have a boat slip. Read more »
    • Chincoteague Island
    • Sunset Bay Villa
    • Condo
    • Sleeps 8
    • 3 beds, 2 bathrooms
    • View Details
    Sunset Bay Villa 116
    6321 Captain's Lane #116
    Chincoteague Island VA
    37.9327866, -75.3813864
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800-668-7836 | rentals@chincoteagueresort.com | http://www.chincoteagueresort.com | 6426 Maddox Blvd, Chincoteague Island, VA 23336