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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. Sunset Cove

    Peace and tranquility is what Sunset Cove offers! This beautiful 4 bedroom waterfront home in the Smugglers Cove area is nestled on the northwestern shoreline of Chincoteague Island. You'll find 3 bedrooms upstairs (Q/4T) and the fourth bedroom downstairs (Q). Enjoy all the modern amenities, including fireplace and outside shower, and open floor plan. The porches (screened and open) are the perfect place to watch the unsurpassed sunsets over the Chincoteague Bay at the end of the day. Note: This property has a 7 night minimum during all seasons. Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 8
    • 4 beds, 2.5 bathrooms
    • View Details
    Sunset Cove
    4446 Shady Lane
    Chincoteague Island VA
    37.9539217, -75.3469762
  2. Tern Inn

    Private Pier, Close to Park

    Tastefully remodeled and comfortably furnished, TERN INN is a delightful 2 bedroom townhome you'll find nestled on the shoreline of the Assateague Channel. Open floor plan, master bedroom suite with balcony, private pier and unobstructed views of the Assateague Lighthouse are just a few of the many features. You're also within walking distance to Memorial Park, Etta's Waterside Restaurant, boat rentals and more. It doesn't get much better than that! NOTE: This rental has dog breed restrictions. If you plan to bring a dog, please confirm with a reservationist. Read more »
    • Chincoteague Island
    • Eastside
    • Condo
    • Sleeps 6
    • 2 beds, 2.5 bathrooms
    • View Details
    Tern Inn
    4092 Channel Lane
    Chincoteague Island VA
    37.9170458, -75.3777001
  3. Sunset Bay Villa 212

    Beautiful Condo - Elevators, Pool, Fitness Room

    A stunning condo that offers you all of the comforts of the Sunset Bay Villa community. Enjoy the community pool and fitness center! This is one of the pet friendly units at Sunset Bay. Note: This villa does not have a boat slip. Read more »
    • Chincoteague Island
    • Sunset Bay Villa
    • Condo
    • Sleeps 6
    • 3 beds, 2 bathrooms
    • View Details
    Sunset Bay Villa 212
    6321 Captain's Lane #212
    Chincoteague Island VA
    37.9322012, -75.380982
  4. The Haven

    Waterfront * Lighthouse View * Room for everyone!

    As one of Chincoteague Resort's newest offerings, we're please to bring you "The Haven" located on the edge of the Assateague Channel! Enjoy spectacular views of the Channel and Lighthouse right from your own private living space! Downstairs features a kitchen, dining area, living room and half bathroom. The second level features 2 bedrooms - one is a master suite with King bed and private bathroom, and the other features a Queen bed. There is also a 2nd full bathroom on this level. The third level features a bedroom (Queen and 2 Twin beds) and a full bathroom. There are multiple decks and there's also 21' of dock space where you can fish, crab, kayak or tie up a small boat. Take a look and book today; this one won't last long! Read more »
    • Chincoteague Island
    • Eastside
    • Townhouse
    • Sleeps 8
    • 3 beds, 3.5 bathrooms
    • View Details
    The Haven
    7544 East Side Road
    Chincoteague Island VA
    37.9171245, -75.3738931
  5. 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
  6. Family Affair

    Fish and Crab From Your Back Door!

    Located on the southern end of the island, Family Affair is a town home with gorgeous views of tidal canal in the backyard easily viewed from both stories, including the spacious second-level balcony. Enjoy the water access (tidal canal) and surround yourself in nature from the shared pier, just feet from the back deck complete with a picnic table. Family Affair features all the modern amenities, including central AC, dishwasher, washer & dryer in unit, and wireless internet. This home is perfect for your next family vacation to Chincoteague Island! Note: The pier is shared with other adjoining townhomes and is on a small tidal canal. Read more »
    • Chincoteague Island
    • South Ridge
    • Townhouse
    • Sleeps 6
    • 2 beds, 2.5 bathrooms
    • View Details
    Family Affair
    3035 Ridge Road
    Chincoteague Island VA
    37.9094189, -75.397317
  7. Sunset Bay Villa 203

    Beautiful Condo - Elevators, Pool, Fitness Room

    Villa 203 is a new unit that has been professionally decorated and offers five-star luxury. Spacious and accommodating, the gourmet kitchen is perfect for cooking your favorite meals. It's well stocked and ready for your handiwork. There are three bedrooms, including a master bedroom suite with private luxury bath and private exit to the waterside balcony. A small laundry room within the unit houses your washer and dryer. Your stay also includes use of the Sunset Bay marina, pool and fitness areas. Come. Enjoy! Note: This property does not include access to a boat slip. Maximum of 1 small pet (under 50 lbs.). Read more »
    • Chincoteague Island
    • Sunset Bay Villa
    • Condo
    • Sleeps 6
    • 3 beds, 2 bathrooms
    • View Details
    Sunset Bay Villa 203
    6321 Captain's Lane #203
    Chincoteague Island VA
    37.9322012, -75.380982
  8. Bayside II

    Water Views & Great Spaces!

    Bayside II is a well appointed, WATER VIEW, 3-bedroom duplex located just off of South Main Street on the quiet southern end of the island. This spacious, nearly 2,000 sq ft. home offers a family of up to 8 an open floor plan with plenty of space to enjoy. The home has 3 decks - 2 facing the Chincoteague Bay, and a large rear deck to enjoy the evenings and the aroma from dinner cooking on the charcoal grill. Features include a spacious kitchen (with all appliances) adjoining the dining room, a bright and open living room with a fireplace and game/puzzle area, satellite TV, wireless internet, and a master bath with jetted tub. The downtown shops, Memorial Park, Pony Swim area, beach, and the sights and sounds of Maddox Blvd. are a short ride away, but far enough to get away from the hustle and bustle. Have a larger group? Combine Bayside II with any of our other adjoining homes - Sunset Dreams, Bayside or Sunset Dreams II. Note: Bayside II offers water views, however, this rental does not include water access or access to the dock. Read more »
    • Chincoteague Island
    • South Main
    • Duplex
    • Sleeps 8
    • 3 beds, 2.5 bathrooms
    • View Details
    Bayside II
    7516 Doe Bay Lane
    Chincoteague Island VA
    37.913325, -75.3948822
  9. Mermaid Crossing

    Complete Package - Great Amenities

    Comfortable, pet friendly home on large, side-creek lot with fantastic views from both the front and back of house! Excellent crabbing from dock! (Property sits on creek only suitable for kayaks, canoes and crabbing.) Just a short distance to Memorial Park and Fairgrounds. 2 living room areas, 2 full baths, well-equipped kitchen, dishwasher, washer/dryer, outdoor shower, 1-car garage, Direct TV, wireless internet, DVD, BBQ grill, 4 adult beach cruisers (bring your own helmet), 2 kayaks, crab traps and net, games, books, puzzles, and some beach gear! Read more »
    • Chincoteague Island
    • In Town
    • Single Residence
    • Sleeps 10
    • 3 beds, 2 bathrooms
    • View Details
    Mermaid Crossing
    3386 Hook Drive
    Chincoteague Island VA
    37.9221492, -75.3834261
  10. 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
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800-668-7836 | rentals@chincoteagueresort.com | http://www.chincoteagueresort.com | 6426 Maddox Blvd, Chincoteague Island, VA 23336