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!

  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  7. 7
  8. 8
  9. 9
  10. 10
  11. >
  1. Sunset Bay Villa 116

    Beautiful Condo - Elevators, Pool, Fitness Room

    A beautiful ground-floor villa with walk out to marina. Luxurious master bedroom with private bath includes both a roomy tiled shower and whirlpool bath. Villa 116 will sleep 8 (beds for 6 plus a queen size air mattress), and includes a full laundry, all appliances, a gourmet kitchen, and more. There's also a pool and fitness room for your enjoyment! Tastefully furnished, you can relax, enjoy and entertain your family and friends in style. NOTE: This unit does not have a boat slip. Read more »
    • Chincoteague Island
    • Sunset Bay Villa
    • Condo
    • Sleeps 8
    • 3 beds, 2 bathrooms
    • View Details
    Sunset Bay Villa 116
    6321 Captain's Lane #116
    Chincoteague Island VA
    37.9327866, -75.3813864
  2. Wildflower

    Long Pier for Boating, Fishing and Crabbing,

    Beautiful waterfront home with shared pier plus floating dock on deep water!! Ground level is a large screened patio perfect for those summer time seafood feasts. The first level is great room boasting reclaimed barn board walls and wide plank pine floors with a separate den and full bath. There is a second screened porch overlooking that water from the great room. The second level has a large waterfront master suite with a private balcony, two more bedrooms and another full bath. Close to Memorial Park right across the street from a family restaurant! (Spiral staircase in home, may not be suitable for small children.) For larger groups for family reunions, check out nearby Moon Rising or Herbie's Hideaway! Read more »
    • Chincoteague Island
    • South Ridge
    • Single Residence
    • Sleeps 6
    • 3 beds, 3 bathrooms
    • View Details
    Wildflower
    7381 Hickman Lane
    Chincoteague Island VA
    37.9161709, -75.3852815
  3. Moondance

    Picture Perfect Location - Easy Kayak Launch

    Beautiful bay-front home overlooking Oyster Bay - a kayakers' paradise. Your group of 8 will enjoy the peace & quiet this home has to offer. There's a dock with floating boat launch for easy in/easy out. As you enter this home, on the main level you'll find a great open floor plan with stunning water views from every room. There's an open kitchen/dining/living area with fireplace and private bedroom (2T) and den downstairs. The second level offers 3 additional bedrooms (K/Q/2T) and 2 more full bathrooms. Come, stay, relax... this is the perfect spot! Read more »
    • Chincoteague Island
    • North Main
    • Single Residence
    • Sleeps 8
    • 4 beds, 3 bathrooms
    • View Details
    Moondance
    5148 Twilley Drive
    Chincoteague Island VA
    37.9519147, -75.3463511
  4. Pelican's Roost

    New Vacation Rental * Popular East Side Location * Water Views

    We're pleased to be able to offer "Pelican's Roost" as one of the newest additions to our fine selection of vacation rentals! As the middle unit in a triplex, Pelican's Roost offers fabulous water views and expansive porch and deck areas. You'll enjoy the bright and spacious open floor plan downstairs, featuring the kitchen, dining and living room areas. There's also a 1/2 bathroom and a sliding door that leads to the screened porch (perfect for outside dining or watching the kayakers float by...) and open deck areas. Upstairs you'll find a full bathroom and two bedrooms. The open, spacious master bedroom features a waterside sitting area, complete with glass deck railings, so that you can lounge inside or outside, and watch the tides and wildlife. Coming for the Pony Swim? This is the IDEAL location - enjoy spectacular views of where the ponies swim across the channel and their rest area! Tastefully furnished and appointed, you won't be disappointed at Pelican's Roost! NOTE: This rental does not have cable/satellite TV. The living room TV does have a plug-in for TV sticks and there is a DVD player. Read more »
    • Chincoteague Island
    • South Ridge
    • Townhouse
    • Sleeps 6
    • 2 beds, 1.5 bathrooms
    • View Details
    Pelican's Roost
    3412 Ridge Road
    Chincoteague Island VA
    37.9153675, -75.3856566
  5. Sunset Bay Villa 221

    Beautiful Condo - Elevators, Pool, Fitness Room

    COME AND ENJOY! You've earned it. Located on the edge of beautiful Chincoteague Bay, Sunset Bay Villa 221 is a luxury waterfront condominium that sleeps 8 with three rooms for sleeping. This unit boasts over 1,700 square feet of luxury living space with all amenities - waterfront balcony, master bedroom suite, wood floors, chef-quality kitchen, pool, fitness room, internet access, and large open rooms. Dock your boat -- there's a reserved boat slip in a protected marina available, all just steps away from your door! This corner unit is full of natural lighting for a more bright, open feel! And to top it off, you can even BRING YOUR DOG! Upper levels are serviced by an elevator - no lugging heavy bags up stairs! Note: One of the twin beds is a pull-out style bed. This rental is pet friendly for dogs only (2 max.). Read more »
    • Chincoteague Island
    • Sunset Bay Villa
    • Condo
    • Sleeps 8
    • 3 beds, 2 bathrooms
    • View Details
    Sunset Bay Villa 221
    6321 Captain's Lane #221
    Chincoteague Island VA
    37.9322012, -75.380982
  6. Blissful Way

    Great Screened Porch for BBQs!

    This lovely vacation rental home features 3 bedrooms and 2 bathrooms, including a 1st floor master suite with a queen bed. Blissful Way is very bright and airy with a large living room/Dining Area. Off of the kitchen is a screened porch great for family bar-b-ques. Upstairs you'll find two more large bedrooms with high cathedral ceilings and another full bathroom. Television and wireless internet is provided. This home is nestled on a quiet cul-de-sac, and Capt. Bob's Marina is very close by! It's only a 10-minute drive to the beach. Enjoy a blissful vacation at Blissful Way! Read more »
    • Chincoteague Island
    • South Ridge
    • Duplex
    • Sleeps 7
    • 3 beds, 2 bathrooms
    • View Details
    Blissful Way
    8152 Marsh Point Lane
    Chincoteague Island VA
    37.9095365, -75.3962687
  7. 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 (ID 4810983) or Sunset Dreams II (ID 3943138)! 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 10
    • 3 beds, 2.5 bathrooms
    • View Details
    Bayside
    3068 Main Street
    Chincoteague Island VA
    37.9135205, -75.3956594
  8. Admiral Benbow

    Fish & Crab at the Community Harbor!

    A very nice contemporary home located in Oyster Bay I. Located next to the community boat ramp - you have access to the water and the kids can fish and crab from the dock areas. This house has an outdoor ramp to the ground level. Don't miss out on the great screened porch for a family dinner. Bed sizes allow the perfect set up for families of all ages! Read more »
    • Chincoteague Island
    • Oyster Bay
    • Single Residence
    • Sleeps 8
    • 3 beds, 2.5 bathrooms
    • View Details
    Admiral Benbow
    5426 Pearl Drive
    Chincoteague Island VA
    37.9433329, -75.3476952
  9. Channel View

    Nice Rental * Great Price!

    Tastefully remodeled 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! 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
  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
  1. 1
  2. 2
  3. 3
  4. 4
  5. 5
  6. 6
  7. 7
  8. 8
  9. 9
  10. 10
  11. >
800-668-7836 | rentals@chincoteagueresort.com | http://www.chincoteagueresort.com | 6426 Maddox Blvd, Chincoteague Island, VA 23336