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. Pony View

    Pet Friendly! New kitchen!

    Enjoy one of the most amazing, unobstructed views of Assateague Bay and Island from the comfort of your own waterfront deck and second floor balcony! Watch the ponies in the distance on the island, abundant waterfowl, or maybe even catch a glimpse of dolphins in the bay. Two kayaks are also provided for you to enjoy a close-up view of the ponies and all the other amazing wildlife you will find in the bay. Many upgrades have been done to the home recently! The entire first floor including the kitchen was fully renovated in 2018, and a new full bathroom added on third floor in 2019. New carpeting will be installed throughout for the 2020 season. Ceiling fans have also been installed in all 3 bedrooms. The home has central air/heat, washer/dryer, BBQ grill and a fully stocked kitchen with microwave, dishwasher, crock-pot, steamer pots, etc. We have a deep-water dock with a public boat ramp just two docks down. There is off street parking for two vehicles in front of the home, and an extra spot for a boat trailer at the side of the property. We are pet friendly so your best friend can come fishing, too! Memorial park is in walking distance with volleyball, tennis courts and more. Come for a great stay at Pony View! NOTE: No smoking permitted. Linens and towels not included. Read more »
    • Chincoteague Island
    • Eastside
    • Townhouse
    • Sleeps 10
    • 3 beds, 3.5 bathrooms
    • View Details
    Pony View
    7554 Eastside Drive
    Chincoteague Island VA
    37.9173024, -75.373657
  2. Sunset Bay Villa 316

    Beautiful Condo - Elevators, Pool, Fitness Room

    This beautiful bayside villa, professionally decorated, features luxury amenities including a walk-out from the living room area to a private deck. The master bedroom suite is a dream come true - beautiful tiled shower, jetted tub and more. The gourmet kitchen will please your senses. This 3 bedroom villa will sleep 8 and features wireless internet. Sunset Bay Villas also feature a pool and fitness room for your enjoyment, as well as a large marina area. You can stroll to our historic downtown area for shopping, fine dining, movies and more. Come and enjoy! Note: This villa has access to a boat slip. Read more »
    • Chincoteague Island
    • Sunset Bay Villa
    • Condo
    • Sleeps 8
    • 3 beds, 2 bathrooms
    • View Details
    Sunset Bay Villa 316
    6321 Captain's Lane #316
    Chincoteague Island VA
    37.9327866, -75.3813864
  3. Sunny Shack

    Beautifully Furnished & Decorated * Pier * Sunset View

    Words cannot describe this top-of-the-line luxury townhome. The moment you walk in, you'll find a game room with pool table board games and a large flat screen TV. The second level is a spacious open floor plan with views of the water from just about everywhere. The chef's grade kitchen has stainless steel JenAir appliances & a beautiful granite counter tops with a large breakfast bar. The open deck off of the great room has a propane grill and a dining table. There are 3 bedrooms all with flat screen TVs and two bathrooms on this level as well. One is a master suite with a large bathroom queen bed and balcony. The second bedroom has two bunk beds, one with two twins and the second with a full/twin. The third bedroom also has a queen bed. Sunny Shack is a very popular and books quickly, don't miss the opportunity to share this home with family and/or friends. Note: The pier is shared with other adjoining townhomes. Read more »
    • Chincoteague Island
    • South Main
    • Townhouse
    • Sleeps 10
    • 3 beds, 2 bathrooms
    • View Details
    Sunny Shack
    3032 Main Street
    Chincoteague Island VA
    37.9107681, -75.3987811
  4. Island Retreat

    Fun and Affordable with Water Views!

    Island Retreat is a nicely appointed duplex home featuring 3 bedrooms and 2 bathrooms. Situated on Eel Creek with a large screened porch, this home offers amazing views of Chincoteague's wildlife. Downstairs is an open living room, dining area, a full bathroom and two bedrooms (Queen and Full/Twin Bunk). The entire upstairs is a private master suite with a it's own bathroom and balcony. Island Retreat offers Wireless Internet, TV in every room, fully equipped kitchen and more. Come and see for yourself! Please note: This home has 1 parking space. Read more »
    • Chincoteague Island
    • In Town
    • Duplex
    • Sleeps 7
    • 3 beds, 2 bathrooms
    • View Details
    Island Retreat
    6767 Megan Drive
    Chincoteague Island VA
    37.9282832, -75.3622335
  5. Captain Mike's Cottage

    Brand New Home * 3 Pools * Golf * Marina

    Clean, cool, comfortable and BRAND NEW! What more could you ask for?! As one of Chincoteague Resort's newest vacation rental listings, we're excited to be able to offer you 'Capt. Mike's Cottage'! Featuring all new furniture and amenities, and tastefully decorated in a beachy-chic theme, you'll be sure to enjoy a fabulous vacation in this wonderful home. There's a TV in the living room and 2 of the bedrooms for your enjoyment. Stainless steel appliances, granite countertops, custom vanities, and 2 adult bicycles complete the package! Located within the Captains Cove community, this rental includes access to the community amenities such as 3 pools (2 outdoor, 1 indoor), tiki bar, marina, restaurant, golf course, playground and more! (Small daily fee applies for pool and golf course use.) Free WIFI at the Marina Club! Read more »
    • Captain's Cove
    • Captain's Cove
    • Single Residence
    • Sleeps 8
    • 3 beds, 2 bathrooms
    • View Details
    Captain Mike's Cottage
    37283 Davey Jones Blvd.
    Greenbackville VA
    38.0064824, -75.4196168
  6. Sea Star

    One of our Most Popular Rentals!

    You cannot go wrong with this brand new beautiful vacation home!! Walking to restaurants, movies, shopping or anything else is just minutes away. Sea Star is a single story 3 bedroom 2 bathroom home that is tastefully furnished and decorated from top to bottom. The master suite boasts a queen bed and a beautiful bathroom with tiled walk in shower, dual vanity and a soaking tub. The great room is spacious and bright with a large kitchen and laundry room. There are two more bedrooms offering another queen bed and a twin trundle room. This home also features a brand new 14-50 NEMA outlet for charging electric vehicles! You won't be disappointed! Read more »
    • Chincoteague Island
    • In Town
    • Single Residence
    • Sleeps 6
    • 3 beds, 2 bathrooms
    • View Details
    Sea Star
    4333 Anderton Avenue
    Chincoteague Island VA
    37.9318987, -75.3690743
  7. Water's Edge

    Newly Remodeled and Fabulous!

    Water's Edge is an adorable Bay Front cottage in walking distance to Chincoteague's Historic Downtown. You'll be impressed by the charm of this home from the time you pull in the driveway. On the first floor you'll find a full bathroom with an open great room with expansive bay views. There is a large screened porch that leads to an open sundeck that is extended by a private deep water pier with a floating dock. The second level offers two bedrooms and one full bathroom. The master bedroom has a queen bed, private balcony and tower room with panoramic views. The second bedroom offers two bunk beds. Off of the hall is a large second level deck with breathtaking Sunset Views of the Chincoteague Bay. Don't miss the opportunity to book this little slice of heaven... (Note: Woodstove is not usable.) Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 7
    • 2 beds, 2 bathrooms
    • View Details
    Water's Edge
    4501 Main Street
    Chincoteague Island VA
    37.9418372, -75.3667824
  8. 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
  9. 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
  10. Hill House

    Big House with Convenient Location

    Welcome to Hill House! Wonderful traditional island home with fantastic upgrades! The kitchen has been renovated, along with the bathrooms. Excellent in town location, walk to dinner, movie, shopping & galleries. Hill House features 4 bedrooms and 2.5 bathrooms, with a first floor bedroom (double/twin Bunk) & 1/2 bath. Three more bedrooms on the second floor with a master suite (king) that offers a private staircase to the dining room. The third bedroom (queen) and fourth (two twins) are also located on the second floor. Hill House is now pet friendly as well! Read more »
    • Chincoteague Island
    • In Town
    • Single Residence
    • Sleeps 9
    • 4 beds, 2.5 bathrooms
    • View Details
    Hill House
    3884 Main Street
    Chincoteague Island VA
    37.9318542, -75.3800117
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800-668-7836 | rentals@chincoteagueresort.com | http://www.chincoteagueresort.com | 6426 Maddox Blvd, Chincoteague Island, VA 23336