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. Sunset Bay Villa 312

    Beautiful Condo - Elevators, Pool, Fitness Room

    Villa 312 is a beautiful 3 bedroom villa featuring a master bedroom suite with luxury bath, gourmet kitchen with center island which is great for entertaining, laundry room with washer/dryer and a waterside balcony overlooking Chincoteague Bay. There are tvs in all the bedrooms, and a computer desk to work from. Villa 312 will sleep 8, and features lots of extras including beach gear and baby gear for your use, as well as a 14' boat slip. Your rental also includes the use of the Sunset Bay pool and fitness area. Located adjacent to our historic downtown area, where you'll find gourmet food shops, boutiques, a public library, galleries and fine dining - all with a short stroll. Come and enjoy a Sunset Bay vacation! Note: This villa has access to a 14' boat slip. Linens and/or towels are optional and can be provided upon your arrival - please inquire about our linen packages. This property is NO SMOKING & NO PETS. Read more »
    • Chincoteague Island
    • Sunset Bay Villa
    • Condo
    • Sleeps 8
    • 3 beds, 2 bathrooms
    • View Details
    Sunset Bay Villa 312
    6321 Captain's Lane #312
    Chincoteague Island VA
    37.9327866, -75.3813864
  2. Sunset Bay Villa 206

    Beautiful Condo - Elevators, Pool, Fitness Room

    Villa 206 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. Villa 206 will sleep 8, and there are a total of 4 TVs. A laundry room within the unit houses your washer & dryer. Your stay also includes use of the Sunset Bay marina, pool and fitness areas. Come. Enjoy! Note: This property does not have a boat slip, however, use of the marina is included. 7-night minimum stay is required during all seasons. Linens and/or towels are optional and can be provided upon your arrival - please inquire about our linen packages. This property is NO SMOKING & NO PETS. Read more »
    • Chincoteague Island
    • Sunset Bay Villa
    • Condo
    • Sleeps 8
    • 3 beds, 2 bathrooms
    • View Details
    Sunset Bay Villa 206
    6321 Captain's Lane #206
    Chincoteague Island VA
    37.9322012, -75.380982
  3. Cozy View

    Main St. Water Views! Perfect beach getaway!

    A true architectural delight, "Cozy View" is one of Chincoteague Island's unique gems. Conveniently located on North Main Street, this cottage is close enough to town, yet just far enough away to offer some peace and quiet. The stunning water views of the Chincoteague Bay and million-dollar sunsets are sure to please the senses. The main living level features a fabulous screened porch (perfect for lounging after a day at the beach or dining al fresco), the living room and a dining area (with drop-leaf table), kitchen, bedroom (two twin beds) and a full bathroom with tub and shower. The entire upstairs is a private master bedroom with en suite bathroom and access to the second-level sundeck. "Cozy View" was strategically and thoughtfully designed so that each room captures panoramic views of Chincoteague Bay. Come and enjoy a wonderful vacation at this comfortable and cozy escape! NOTE: This home will accomodate up to 5 guests with a queen bed, two twin beds, and a sofa in the living room (sofa is not a pull-out sleeper sofa). Linens and/or towels are optional and can be provided upon your arrival - please inquire about our linen packages. This property is NO SMOKING & NO PETS. Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 5
    • 2 beds, 2 bathrooms
    • View Details
    Cozy View
    5052 Main Street
    Chincoteague Island VA
    37.946288, -75.3592654
  4. Channel View

    East Side Location * Water Views

    Tastefully and simply adorned beach home featuring a reverse floor plan and spectacular views of the Assateague Channel and Lighthouse! Located on the popular East Side of Chincoteague Island, Channel View is conveniently located near a public boat ramp, restaurants and Memorial Park. And you're about a mile from the beach and downtown area! Downstairs there's 2 bedrooms, a den (twin sleeper sofa), a bathroom and screened porch. Upstairs you'll find a bright, airy kitchen, living room, bathroom and bedroom. Channel View also has a spacious yard for your outdoor activities. Come see for yourself - this may be your perfect vacation spot! Please note: Linens and/or towels are optional and can be provided upon your arrival - please inquire about our linen packages. This property is NO SMOKING & NO PETS. Read more »
    • Chincoteague Island
    • Eastside
    • Single Residence
    • Sleeps 6
    • 3 beds, 2 bathrooms
    • View Details
    Channel View
    7177 Wayne Road
    Chincoteague Island VA
    37.9223007, -75.3675297
  5. Avalon

    Oyster Bay I Community * Waterside Screened Porch

    Avalon is a charming 4 bedroom, 2.5 bathroom home situated on a bulkheaded waterfront lot on Oyster Bay! There is a large great room that boasts two family rooms, a dining area and large kitchen. From the gas fireplace, to the 16' cathedral knotted pine ceilings, this home is bright, warm and inviting. Avalon offers two queen bedrooms with screened porch access (one private) and two twin bedrooms. Offering over 600 sq. ft. of screened porch - you could live outdoors! The first level also offers a full size futon and 1/2 bath. Avalon is one of our most popular offerings; it books quickly! Please note: Linens and/or towels are optional and can be provided upon your arrival - please inquire about our linen packages. This property is NO SMOKING & NO PETS. Read more »
    • Chincoteague Island
    • Oyster Bay
    • Single Residence
    • Sleeps 10
    • 4 beds, 2.5 bathrooms
    • View Details
    Avalon
    5421 Hibiscus Court
    Chincoteague Island VA
    37.945001, -75.3502309
  6. 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
  7. Blue Point

    Popular Vacation Home * Pet Friendly * Large Screened Porch

    Come for an old fashioned family vacation. This wonderfully maintained classic Chincoteague-style home features a large screened porch and beautiful, spacious yard for those warm summer evenings. A great enclosed outside shower comes in handy for rinsing the sand off after a long day at the beach. Downstairs there is a family room with a wood stove, living room/library with a TV and an eclectic selection of books, a formal dining room, full bath and kitchen. Upstairs there are three bedrooms and a full bathroom. Bring your kids and pets along, there is plenty of room to play! Please note: Linens and/or towels are optional and can be provided upon your arrival - please inquire about our linen packages. This property is NO SMOKING & PET FRIENDLY (with fee). Read more »
    • Chincoteague Island
    • In Town
    • Single Residence
    • Sleeps 6
    • 3 beds, 2 bathrooms
    • View Details
    Blue Point
    3262 Colona Street
    Chincoteague Island VA
    37.924637, -75.3873969
  8. Grey Heron

    Beaiutiful Bayfront Home * Amazing Sunsets * Pet Friendly

    Grey Heron is an amazing contemporary waterfront home nestled on the shoreline of Chincoteague Bay. You'll love the floor plan; a terrific great room with wood floors flanked by a kitchen on one side and a fireplace on the other. And great windows throughout! There's also a "sitting room" with build in wrap-around benches and 180* water views. It's wonderful! Each room is designed so that there are unobstructed, panoramic views of the bay and marshes - including breathtaking sunsets! The first level also features two private bedrooms that share a full bath. The second story (accessible by the spiral staircase) is a master bedroom suite and bathroom. There are numerous balconies and a lot of outdoor space. The screened porch is perfect for dining alfesca and there ample deck area right off the living area. Grey Heron is located just north of town so you're not too far from restaurants, shopping, movies and more! Bring the 4-legged family members; Grey Heron is pet friendly! Please Note: Linens and/or towels are optional and can be provided upon your arrival - please inquire about our linen packages. This property is NO SMOKING & PET FRIENDLY (with fee). Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 8
    • 3 beds, 2 bathrooms
    • View Details
    Grey Heron
    5123 Main Street
    Chincoteague Island VA
    37.9479336, -75.3568049
  9. Willaway

    Ridge Road * Large Yard * Screened Porch *

    We are excited to offer one of our newest rentals in our inventory, Willaway! Located off of South Ridge, within walking distance of Tom's Cove, this sweet home sits tucked behind mature crepe myrtles situated on a large lot. Tastefully decorated, clean, and comfortable, Willaway features everything you're looking for in a rental. The living room features abundant seating with a large TV. The kitchen is equipped with a Keurig Coffee maker, dishwasher, full size refrigerator, gas range, microwave, and toaster oven. The Master bedroom features a King size bed, a flat screen TV, and an en suite with a stand up shower and separate large bathtub that connects to the mud room and laundry room that features a full size washer and dryer. The other end of the home features two more bedrooms, both featuring flat screen TVs, the first featuring a Queen bed, and the second featuring a bunk bed that features a Double bed on the bottom bunk, and a Twin bed on top bunk. Off the hallway on this side of the home is another full bathroom. Outside, you will find a large screened in porch with ample comfortable seating, deck space, a picnic table, and a propane grill; all perfect for outdoor dining with the family. The partially fenced in yard has plenty of room for children to run around, play, and enjoy the Chincoteague sunshine. When there's a will, there's a way- so book your stay at Willaway today! Please Note: Linens and/or towels are optional and can be provided upon your arrival - please inquire about our linen packages. This property is NO SMOKING & PET FRIENDLY (with fee). Read more »
    • Chincoteague Island
    • South Ridge
    • Single Residence
    • Sleeps 10
    • 3 beds, 2 bathrooms
    • View Details
    Willaway
    3104 Ridge Road
    Chincoteague Island VA
    37.9103232, -75.393831
  10. Cove's Point

    Waterfront Location * Pool * Boat Dock * Golf

    As one of our most popular selections, we're pleased to be able to offer you this fabulous waterfront retreat - "Cove's Point"! Aptly named, this home is situated at Cockle Point and offers over 200 degree views of the Chincoteague and Horntown Bays. Enjoy the sunrise and sunset - the best of both worlds! The floor plan was strategically designed to take advantage of the location and capture unobstructed water views from every room. Enjoy the bright, open spaces with expansive windows. On the first floor you'll find the main living areas, including a sunroom, and a master bedroom suite with bathroom. The second floor features two more bedrooms and another full bathroom. Enjoy the coastal breezes from any of the 3 decks/balconies and 4 flat screen TV's with WiFi. Bring your boat - there's a private deep water pier that extends into the bay with a boat lift. Cove's Point is now PET FRIENDLY! In addition to all the fine features of this vacation home, you'll also enjoy all the community amenities that Captain's Cove has to offer! This includes 3 pools (2 outdoor & 1 indoor), tiki bar, fitness center, waterfront restaurant and marina club, boat launch, 9-hole golf course, kid's playground and so much more - all just minutes from the home! Small fee applies for usage of community amenities. Please note: Linens and/or towels are optional and can be provided upon your arrival - please inquire about our linen packages. This property is NO SMOKING & PET FRIENDLY (with fee). Read more »
    • Captain's Cove
    • Captain's Cove
    • Single Residence
    • Sleeps 10
    • 3 beds, 2.5 bathrooms
    • View Details
    Cove's Point
    37548 Bayside Drive
    Greenbackville VA
    37.9871732, -75.4095482
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800-668-7836 | rentals@chincoteagueresort.com | http://www.chincoteagueresort.com | 6426 Maddox Blvd, Chincoteague Island, VA 23336