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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. The Virginian

    Room for the Whole Gang - Crabbing

    Light, bright & airy, "The Virginian" is a wonderfully large vacation home that boasts a full ensemble of amenities along with a nice waterfront setting. Downstairs you'll find a large living/dining room combo and a nice modern kitchen. Off the kitchen is a private den area - a perfect spot to catch up on your reading! There's a half bath on the first floor. All bedrooms are on the second level. There's a master bedroom suite as well as another full bath on the second level. The Virginian features central heat and air, laundry facilities, garage and more. Located on a bulkheaded lot on a canal that comes up from Oyster Bay, you can through your crab pot in right outside the back door. NO SMOKING/NO PETS Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 11
    • 4 beds, 2.5 bathrooms
    • View Details
    The Virginian
    5065 Twilley Drive
    Chincoteague Island VA
    37.9506003, -75.3439689
  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. Langtree

    One of our Most Popular Rentals

    Your home away from home... enjoy the water views, bring your boat and use your own dock or just relax and listen to the whispering pines. Great views of Oyster Bay off the front deck. 3 Bedrooms, 2 full baths (plus another shower/bath downstairs), outside shower, washer and dryer, satellite TV, and PET FRIENDLY! Front and rear decks, both with water views, large screened porch. Sleeps 10 people. Note: This property has a 7 night minimum stay during all seasons. Read more »
    • Chincoteague Island
    • Oyster Bay
    • Single Residence
    • Sleeps 10
    • 3 beds, 3 bathrooms
    • View Details
    Langtree
    5388 Sunrise Shore Drive
    Chincoteague Island VA
    37.943186, -75.346406
  4. Aramabad

    Bike to the Beach! Walk to Dinner!

    This beautiful 4 bedroom, 2 bathroom home could be the ideal vacation home for your family and friends. Located on Oak Drive in Piney Island, this home is an easy bike riding distance to the beach and trails of Assateague Island. Aramabad has a completely renovated kitchen with granite counter tops and modern appliances. There are two bedrooms and full bathroom on the first floor. One offering a queen bed, and the second two twin beds. The second level offers two more bedrooms (queen and two twins) and another full bathroom. The two bathrooms were recently renovated as well. The outside is a private wooded lot with a great screened porch that exits to a fully enclosed outdoor shower. There is a comfortable covered front porch for enjoying coffee or relaxing after a day at the beach. Piney Island offers a shared community water access area perfect for launching kayaks and canoes. Read more »
    • Chincoteague Island
    • Piney Island
    • Single Residence
    • Sleeps 8
    • 4 beds, 2 bathrooms
    • View Details
    Aramabad
    5337 Oak Drive
    Chincoteague Island VA
    37.9253828, -75.3522658
  5. 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
  6. 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
  7. 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
  8. Blue Sea Star

    New Construction and Quiet Location!

    Welcome to Blue Sea Star! You'll fall in love with this fabulous 3 bedroom, new construction home from the moment you walk in the door. Bright open spaces, lots of windows, wood floors, first floor master bedroom/bathroom, and too much more to name! Located on a quiet cul-de-sac in Oyster Bay II Community, Blue Sea Star also features a screened back porch, open side and front porches, and a great backyard. As a pet friendly rental, you can even bring your four-legged family member! Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 12
    • 3 beds, 2.5 bathrooms
    • View Details
    Blue Sea Star
    5199 Pine Tree Way
    Chincoteague Island VA
    37.9476834, -75.3532993
  9. Drop Anchor

    "Drop Anchor" is a luxury rental home nestled on a quiet cul-de-sac beneath the tall pines. All amenities including a great open kitchen, screened porch, wireless internet, gas fireplace and bedrooms on both levels. The upstairs master bedroom suite is spacious and inviting, and this home features updated electronics and beautiful windows throughout! Read more »
    • Chincoteague Island
    • South Ridge
    • Duplex
    • Sleeps 8
    • 3 beds, 2 bathrooms
    • View Details
    Drop Anchor
    8176 Marsh Point Lane
    Chincoteague Island VA
    37.9092648, -75.3958133
  10. 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
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800-668-7836 | rentals@chincoteagueresort.com | http://www.chincoteagueresort.com | 6426 Maddox Blvd, Chincoteague Island, VA 23336