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. A Getaway

    Great Screened Porch & Quiet Location

    A Getaway is a bright and cozy home nestled between pink Crape Myrtles in the private, secluded neighborhood of Oyster Bay II right off of North Main Street. This home features a 12 x 24 screened in deck that is perfect for outdoor gatherings, dinners, and making memories. With clean, functional living spaces, bright bedrooms, and great outdoor spaces, this home is the perfect getaway for you and your family! Read more »
    A Getaway
    5250 Pine Tree Way
    Chincoteague Island VA
    37.9479541, -75.3530019
  2. Aerie (Sunset Bay 120)

    Beautiful Condo - Marina, Pool, Fitness Room!

    Come and enjoy this beautiful 3 bedroom villa! Conveniently located next to to pool, this ground-level condo allows you to walk right out from your balcony to the marina/dock. Enjoy all of the Chincoteague Island decor, spacious open floor plan, and the master bedroom suite featuring a private bath with jetted tub and private exit to the waterside deck area. The open concept living area is spacious, and the laundry room houses a washer and dryer. This unit features wireless internet, and can sleep up to 6 guests. Come and stay a while; you're sure to capture fond vacation memories here at "Aerie!" Read more »
    • Chincoteague Island
    • Sunset Bay Villa
    • Condo
    • Sleeps 6
    • 3 beds, 2 bathrooms
    • View Details
    Aerie (Sunset Bay 120)
    6321 Captain's Lane #120
    Chincoteague Island VA
    37.932402, -75.38126
  3. Blue Moon

    4 Bedrooms * 2 Screened Porches * Pet Friendly

    Come and enjoy a nice, relaxing vacation at this charming island home. "Blue Moon" is centrally located on Chincoteague Island - it's not too far from downtown, a public boat launch, nature trails, and one of the island's most-loved fresh seafood shops! Downstairs features the living room/dining area combo, a lovely kitchen, full bathroom and 2 screened porches. On the second level you'll find 3 bedrooms and another full bathroom. The third level is the master bedroom suite with a King bed and full bathroom. If you enjoy the more traditional-style cottages, "Blue Moon" might be the one for you! Read more »
    • Chincoteague Island
    • In Town
    • Single Residence
    • Sleeps 8
    • 4 beds, 3 bathrooms
    • View Details
    Blue Moon
    5266 Deep Hole Road
    Chincoteague Island VA
    37.9371616, -75.3523199
  4. Bayside

    Sunsets * Waterfront Dock * Pet Friendly!

    Luxury waterfront townhome overlooking Chincoteague Bay. Beautiful sunsets! Long pier for fishing and crabbing. All amenities including all appliances, central air and enclosed porch (with air conditioning). Need more room? Bayside already booked? Try our sister homes right next door, Sunset Dreams (Homeaway ID 4976271) or Sunset Dreams II (Homeaway ID 4810983)! High speed internet is included with this unit. Note: Pier is shared with the other 2 adjoining townhomes. This rental allows dogs only and has a 2 dog maximum. Read more »
    • Chincoteague Island
    • South Main
    • Townhouse
    • Sleeps 8
    • 3 beds, 2.5 bathrooms
    • View Details
    Bayside
    3068 Main Street
    Chincoteague Island VA
    37.9135205, -75.3956594
  5. Island Estate

    Sleeps 12 * Waterfront * Pet Friendly

    Fabulous, fabulous, fabulous! If you're looking for a large space to have a family vacation or reunion, this is it. This beautiful waterfront home is located on a tidal creek and boasts over 3,000 sq ft of living space. All amenities - central air, all kitchen appliances and more. The formal dining room is great for large gatherings. Beautiful back deck area with private pool for your enjoyment. Island Estate is a PET FRIENDLY home. Note: Pool is open Memorial Day weekend through September 30th (weather permitting). Read more »
    • Chincoteague Island
    • South Main
    • Single Residence
    • Sleeps 14
    • 5 beds, 3 bathrooms
    • View Details
    Island Estate
    7465 Beebe Road
    Chincoteague Island VA
    37.9148623, -75.3922187
  6. Bay Daze

    Fish & Crab From Your Backdoor!

    Escape from the hustle and bustle of everyday life at this little slice of paradise nestled on the edge of the Chincoteague Bay! Bay Daze is a clean, comfortable and modern townhome (end unit) offering all the amenities you'll need for a perfect vacation! On the main level you'll find an open living space featuring a nice kitchen with breakfast bar, dining area, and living room with new furniture! There are water views from every room! Upstairs features 2 bedrooms (both suites with private bathrooms, balconies, and TVs) - one bedroom has a King bed and the other a King bed and trundle daybed. Drop your fishing line in the water right out your back door, or dock your boat for easy access. There is also a garage and on site boat trailer parking. The possibilities are endless at this waterfront property! Call today; this one books quickly. Note: This unit features a private boat dock (slip #5). Read more »
    • Chincoteague Island
    • In Town
    • Townhouse
    • Sleeps 6
    • 2 beds, 2.5 bathrooms
    • View Details
    Bay Daze
    6151 Marsh Island Drive
    Chincoteague Island VA
    37.9358861, -75.3778576
  7. 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 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 if you would like to take a closer look. Bring your boat to your dock with a public boat ramp just two docks down. We are pet friendly so your best friend can come fishing, too. There are two off street parking spaces. Memorial park is in walking distance with a skate park, volleyball, tennis courts and more. Enjoy the comforts of home with central air/heat, microwave, dishwasher, washer/dryer, and a master bedroom balcony. Read more »
    • Chincoteague Island
    • Eastside
    • Townhouse
    • Sleeps 8
    • 3 beds, 2.5 bathrooms
    • View Details
    Pony View
    7554 Eastside Drive
    Chincoteague Island VA
    37.9173024, -75.373657
  8. Cowboy Cottage

    Popular Rental * Pet Friendly

    Cowboy Cottage is a pet friendly home conveniently located a block from Maddox Blvd., and just a couple of blocks from downtown Main Street. This ranch-style home has an open floor plan and is handicap accessible with a ramp to enter the house and bedroom/bathroom accessibility. There is a large screened porch and a fenced in yard that is divided - one side is for your furry family members to run and in the second section there is a swing set and area for the kids. Book this one today! Read more »
    • Chincoteague Island
    • In Town
    • Single Residence
    • Sleeps 6
    • 3 beds, 2 bathrooms
    • View Details
    Cowboy Cottage
    6345 Clark Street
    Chincoteague Island VA
    37.9329181, -75.3680853
  9. Morning Song

    One Of Our Favorite Rentals!

    Nestled on the edge of Assateague Bay and overlooking the wild salt marshes of Assateague and Morris Islands is where you'll find this gem. With capacity for 10 guests, the 4 bedroom 3 bath contemporary ranch home features a pier and dock on deep water, screened porch and open deck area, a widow's walk, 2 fireplaces, a fully stocked kitchen including dishwasher, central heat and air and washer dryer. The open floor plan features bedroom suites on all sides making Morning Song a beautiful place to spend your summer vacation. Home has ramp access. Internet access provided. Read more »
    • Chincoteague Island
    • Oyster Bay
    • Single Residence
    • Sleeps 10
    • 4 beds, 3 bathrooms
    • View Details
    Morning Song
    5440 Deep Hole Road
    Chincoteague Island VA
    37.939142, -75.34735
  10. 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
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800-668-7836 | rentals@chincoteagueresort.com | http://www.chincoteagueresort.com | 6426 Maddox Blvd, Chincoteague Island, VA 23336