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. Shackeau East

    Loyal Following - Shackeau was Rebuilt in 2016

    Check out the NEW Shackeau East! This charming Piney Island waterfront cottage has some of the most amazing views of Assateague Island and has just been newly renovated! With many upgraded amenities, you will fall in love all over again with this great cottage. It is nestled in the tall pines of Pine Drive this house is perfect for that romantic getaway you've been looking for. The living room boasts a great brick wood burning fireplace, and direct access to a spacious screened porch with those amazing views we mentioned before. Call or book online now; this property rents quickly! Read more »
    • Chincoteague Island
    • Piney Island
    • Single Residence
    • Sleeps 4
    • 1 beds, 1 bathrooms
    • View Details
    Shackeau East
    7047 Pine Drive
    Chincoteague Island VA
    37.9247929, -75.346886
  2. 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
  3. Bay Mist

    Community Pool & Water Access!

    Bay Mist is a nice two bedroom town home that features water and lighthouse views. The first floor has a large dining/kitchen area, living room with TV and a half bath. Upstairs features a master suite bedroom (with newly remodeled bathroom) and a private balcony that offers lighthouse/water views, as well as a second full bath (also remodeled) and another bedroom with a double bed and two twins. Lighthouse Estates offers a community pool and water access/shared dock for guests. No smoking/No pets Read more »
    • Chincoteague Island
    • Eastside
    • Townhouse
    • Sleeps 6
    • 2 beds, 2.5 bathrooms
    • View Details
    Bay Mist
    7665 East Side Drive # 7
    Chincoteague Island VA
    37.9194408, -75.3697455
  4. 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
  5. Lighthouse Estates #11

    Community Pool & Waterfront Dock!

    Great 2 bedroom, 2.5 bath townhome in Lighthouse Estates community off East Side Drive. This home features all amenities including central air, washer/dryer and new kitchen appliances. In addition, there is a community pool as well as water access and a dock (shared) to fish and crab from. This is a popular rental - don't wait to book! Read more »
    • Chincoteague Island
    • Eastside
    • Townhouse
    • Sleeps 6
    • 2 beds, 2.5 bathrooms
    • View Details
    Lighthouse Estates #11
    7665 East Side Drive #11
    Chincoteague Island VA
    37.9194408, -75.3697455
  6. Tall Pines

    Charming, Pet Friendly, Popular Rental

    Located in lovely Piney Island within a short bike ride to the beach. This single story 2 bedroom, 1.5 bathroom house offers a large screened porch, fully equipped kitchen and spacious living room. Piney Island offers community water access great for launching kayaks/canoes. To top it all off, Tall Pines is pet friendly with and outdoor dog run in the yard. You won't be disappointed! Note: Water access is a shared with the community just a short distance from the rental home. Read more »
    • Chincoteague Island
    • Piney Island
    • Single Residence
    • Sleeps 6
    • 2 beds, 1.5 bathrooms
    • View Details
    Tall Pines
    5328 Oak Drive
    Chincoteague Island VA
    37.9253384, -75.3523271
  7. Daisey Cottage

    Cute Beach Cottage * Pet Friendly

    Quaint and charming island cottage with all the amenities! Located on the southern end of the island, Daisey Cottage offers everything you'll need for an enjoyable vacation - central a/c, dishwasher, WiFi, washer/dryer and more. And it's even pet friendly! Read more »
    • Chincoteague Island
    • South Ridge
    • Single Residence
    • Sleeps 7
    • 2 beds, 1 bathrooms
    • View Details
    Daisey Cottage
    3293 Ridge Rd
    Chincoteague Island VA
    37.9141686, -75.3891502
  8. Chincoteague Charm

    Main Street Home with 2nd Cottage

    Chincoteague Charm is a beautiful home located on North Main Street. It's just across the street from Chincoteague Bay and there is water access to the bay for kayaks & canoes. The home is very tastefully furnished, has a great kitchen/dining area with center island and quality stainless steel appliances, is air conditioned, and has a laundry area off the back porch. There is a fenced yard and gazebo in the back yard. It's a wonderful home for making family memories. A rental at Chincoteague Charm also includes the use of the guest cottage that sleeps 4, bringing the occupancy capacity to 12 people. Note: The water access with this rental is a natural grassy/marshy area and may be suitable for kayaks/canoes, however, that cannot be guaranteed. Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 12
    • 4 beds, 2.5 bathrooms
    • View Details
    Chincoteague Charm
    4662 Main Street
    Chincoteague Island VA
    37.9446039, -75.3623933
  9. Pony Pen

    Two Bedrooms * Fenced Yard * All Amenities

    Round-up the family and bring them for a memorable vacation at "Pony Pen"! This cute-as-a-button island cottage is located on the southern end of Chincoteague Island, not too far from Captain Bob's Marina, Curtis Merritt Harbor and Memorial (waterfront) Park. Features include 2 downstairs bedrooms, and an open-concept floor plan with the living room, dining area and kitchen. There's a fabulous enclosed front porch; perfect for sipping coffee and watching the island traffic. Off the back of the house you'll find a screened porch and fenced back yard. Perfect for letting the little ones run around and play yard games! As one of our newest vacation rental offerings, you'll want to book quickly. This one will go fast! Read more »
    • Chincoteague Island
    • South Main
    • Single Residence
    • Sleeps 6
    • 2 beds, 2 bathrooms
    • View Details
    Pony Pen
    7546 Beebe Road
    Chincoteague Island VA
    37.9132345, -75.3910626
  10. 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
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800-668-7836 | rentals@chincoteagueresort.com | http://www.chincoteagueresort.com | 6426 Maddox Blvd, Chincoteague Island, VA 23336