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. Amistad

    Grand Victorian on North Main * Great Screened Porch

    This beautiful Victorian is located on Main Street and just a short distance to town. The 4 bedroom home is spacious and very charming with much of it's original integrity still in place. Amenities include central heat & air, all appliances including washer/dryer, outside hot & cold shower, fenced yard, bedrooms on 2 levels and a dog park that is very close by. Downstairs there's a large kitchen, dining room with wine bar, 1/2 bath, living room, and master bedroom suite (Q) with full bath. Upstairs there are 3 more bedrooms, one with D, one with 2D and one with Bunk. There's also another full bath with tub. The 3rd level is a game room w/futon. There's room for everyone at this fabulous charmer - spend your vacation here! 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 10
    • 4 beds, 2.5 bathrooms
    • View Details
    Amistad
    4420 Main Street
    Chincoteague Island VA
    37.9401552, -75.3686013
  2. Drop Anchor

    Great Screened Porch * Southern Location

    "Drop Anchor" is a luxury duplex rental home nestled on a quiet cul-de-sac beneath the tall pines. Featuring all amenities, including a great open kitchen, large screened porch, wireless internet, gas fireplace (off season) and bedrooms on both levels. The upstairs master bedroom suite is spacious and inviting, and this home features updated electronics and beautiful windows throughout! Drop Anchor is located on the southern end of Chincoteague Island, close to the Curtis Merritt Harbor and Capt. Bob's Marina. And, you're just a short drive to town, however, far enough from the hustle & bustle to enjoy quiet evenings. Come and see for yourself - you won't want your stay to end! 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
    • South Ridge
    • Duplex
    • Sleeps 8
    • 3 beds, 2 bathrooms
    • View Details
    Drop Anchor
    8176 Marsh Point Lane
    Chincoteague Island VA
    37.9092648, -75.3958133
  3. Sundance

    Light, bright and airy - this beautiful home is very well maintained, tastefully furnished and boasts all amenities including screened porch, outside shower, all appliances including HE washer/dryer, tvs in every bedroom and more. Sundance features 4 bedrooms and 3 full bathrooms. The home is located just outside of town and offers a very quiet setting - perfect for relaxing and unwinding. There's a master bedroom suite (king) with private bath with soaking tub and separate shower. Blender; Toaster; Coffeemaker (Keurig); Stereo and DVD; Central Heat and Air; HE Washer & Dryer; Phone; Screened Porch; Outside Shower; Gas B- B-Q Grill; Beach umbrella and chairs (located in master closet in king bedroom). Gas Fireplace (only for late fall and winter guests - not available spring, summer and early fall). Parking for 2 cars only. 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
    • South Ridge
    • Single Residence
    • Sleeps 9
    • 4 beds, 3 bathrooms
    • View Details
    Sundance
    4138 Ridge Road
    Chincoteague Island VA
    37.9232535, -75.3754595
  4. 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
  5. Fore Shore

    Captain's Cove * Pet Friendly

    Fore Shore is a charming ranch style home located in the Captain's Cove community that features 4 bedrooms, 2 full bathrooms, and is pet-friendly! The living room of the home offers a flat screen TV and wood stove (off-season). Beyond the living room you find the dining room and kitchen. French doors lead you into a private office/sleeping space with a futon. There is a full bathroom located off the hall, in addition to 3 more bedrooms. The first bedroom features a double bed, the second features two twin beds, and the master bedroom features a queen size bed with an attached full bathroom. Fore Shore also has a large, bright sun room with sky lights and plenty of seating. The glass sun room doors take you out to the multi level deck complete with outdoor table and chairs, a grill, fire pit, and lawn space for kids and pets to run around and play. The Captain's Cove community offers 3 pools (2 outdoor & 1 indoor), tiki bar, Marina Club and restaurant, 9-hole golf course, kids playground, dog park and more! (Small fee applies for usage of community amenities.) And you're only 20 minutes from Chincoteague & Assateague Islands (the beach), and 30 minutes from Ocean City, MD (boardwalk & amusements). 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 8
    • 4 beds, 2 bathrooms
    • View Details
    Fore Shore
    2593 Captain's Corridor
    Greenbackville VA
    37.9968882, -75.4164504
  6. Bayside

    Breathtaking Sunsets * Waterfront Dock * Pet Friendly

    Luxury waterfront townhome overlooking Chincoteague Bay - witness some of the most beautiful sunsets you'll ever see! Long pier for fishing and crabbing. All amenities including modern appliances, central air and enclosed porch (with air conditioning). Need more room? Or is this rental home already booked? Try our sister homes right next door, Sunset Dreams (Homeaway ID 4976271) or Sunset Dreams II (Homeaway ID 4810983)! The convenient South Main Street location means you're just far enough from the 'hustle and bustle', but only a short drive from the downtown area featuring shopping, a waterfront park, library, movie theater, restaurants and so much more! High speed internet is included with this unit. Note: Pier is shared with the other 2 adjoining townhomes. 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; 2 dog limit). 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
  7. 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
  8. Waterman's Daughter

    Snipet Water Views * Bright & Clean * East Side Location

    We are excited to introduce our newest rental Waterman's Daughter! This stately townhome is located on a quiet lane off of East Side Drive. The first floor of the home features two bedrooms, both featuring full attached baths! A full size washer and dryer are conveniently located off the hall in between these bedrooms. As you make your way to the second floor of the home, you are greeted by a bright living space featuring a flat screen TV, fireplace, large windows, and doors that lead you out to the second floor balcony that features a table for two with a view. Right beyond the dining area of the home, you will find the fully equipped kitchen that features additional seating for three at the kitchen bar, a stove top oven, microwave, and dishwasher. The large Master bedroom is on the second floor of the home and features yet another full attached bath and wall-mounted flat screen TV. This home is truly the perfect setting for your next Chincoteague Island vacation; clean, relaxing, and accommodating! Call us or book online 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
    • Eastside
    • Townhouse
    • Sleeps 6
    • 3 beds, 3 bathrooms
    • View Details
    Waterman's Daughter
    7132 Assateague View Lane
    Chincoteague Island VA
    37.9226745, -75.3619541
  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! 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
    • 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. Charlotte's Morning Sun

    Custom Bayfront Luxury * Oyster Bay I * 2 Master Suites

    Set in the boutique residential community of Oyster Bay I, ‘Charlotte's Morning Sun’ is a stunning 5-star waterfront home that offers unobstructed water views and breathtaking vistas of Oyster Bay. Flowing generously over two levels, Charlotte features 4.5 bathrooms and 4 light-filled bedrooms, one of which has it’s own balcony that feels like it’s floating on water. The stylish design offers private and peaceful lounge and dining areas that embrace sweeping bay views that stretch uninterrupted to the horizon. A state-of-the-art chef’s kitchen, a generously-sized waterside screened porch as well as a large observation area allows effortless indoor outdoor living. On the first level you'll find the living room, observation area, chef's kitchen, dining area, 2 bedrooms and a wonderful waterside screened porch. Upstairs you'll find 2 more bedrooms, one with a private balcony. Outside, enjoy exclusive access to the bay via a private dock/boat-slip, or bathe in the outdoor beach shower surrounded by a grassy coastal garden. Just a short drive to the beach, local restaurants and shops, ‘Charlotte’s Morning Sun’ offers an opportunity to secure a luxury vacation home in an exceptional setting. Note: The Oyster Bay I community where this property is located offers a boat ramp that is exclusive to the homes in this community. Water depth may not be suitable for all boats and dock/ramp usability cannot be guaranteed. You can crab and fish at this community harbor area. 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 8
    • 4 beds, 4.5 bathrooms
    • View Details
    Charlotte's Morning Sun
    5321 Sunrise Shore Drive
    Chincoteague Island VA
    37.9197873, -75.3736245
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800-668-7836 | rentals@chincoteagueresort.com | http://www.chincoteagueresort.com | 6426 Maddox Blvd, Chincoteague Island, VA 23336