***6368 Pine Drive-Piney Island*** Brand new Piney Island home. Spacious design open and bright with large screened porch and two covered porches offer views of Assateague in the distance. Close to Edie's Folly. Acess to community boat dock.*** This Property provides Linens & Towels.*** Bed...

***6346 Chester Park DriveI*** Lovely 4 bedroom, 2.5 bath home located in quiet neighborhood is within walking distance to Maddox Blvd and shopping and restaurants. Home sleeps 8 and has nice back patio, screened in gazebo room, outside shower and large gas grill. This home is providing linens...

Jay's Retreat is part of of the owner managed properties of O'Connor Properties. We have hosted over 100 guests in Jay's over the last 2 years and have graciously received many five star reviews. * Perfect for a romantic getaway * Families love crabbing from our dock and kayaking in the bay...

Come stay and relax at this quiet retreat. This listing is a newly remodeled home which is tastefully decorated. There are three color themed bedroom's; which have two queens and two twin sized beds. There is serenity all around you, come sit on the screened in porch and relax while listening to...

5203 Wild Pony Court. Oyster Bay II community. 2 story house located on secluded cul-de-sac. 3 bedrooms, 2 1/2 bathrooms, kitchen, laundry, living, and dining rooms, screened porch, wrap around porch, handicapped ramp, master bedroom on main floor. Private back yard and parking. Located on the...

Totally updated but traditional 'home away from home' facing the Chincoteague Channel on Chincoteague Island, minutes from the quaint downtown and the Assateague National Seashore and Wildlife refuge. Relax in this spacious, clean, and beautifully furnished home with water views of the sunset from...

The Moorings North is an unique architecturally designed luxury 5 bedroom home in the heart of Chincoteague Island. The house is elegantly decorated and has mesmerizing panoramic views of Chincoteague Bay. It is conveniently located in walking distance to small shops, a coffee house, and...

Cute, colorful 2 bedroom cottage with front and back porches. Walking distance to charming old town Main Street shops and restaurants. Back yard with grill and picnic table. Outside shower. Have coffee on the sunny back porch overlooking private back yard. Lots of windows. Wifi. DVDs for...

Sweet Retreat is part of of the owner managed properties of O'Connor Properties. We have hosted over 150 guests in Sweet Retreat over the last 3 years and have graciously received many five star reviews. * Perfect for a romantic getaway * 3 bedrooms, 2 bath, marsh-view home, located in...

ANOTHER DAY IN PARADISE CHINCOTEAGUE BEAUTIFUL BAY FRONT CONDO WITH AMAZING WATER VIEWS Owner operated by: Annie Switzer Call 240/498/0074 *** Booking Fall 2018 *** PLEASE CONTACT OWNER BEFORE BOOKING SUMMER 2019 Unit 213 - 'Sunset in Paradise' at Sunset Bay Villas *** Please see FKN 7097918...

Peaceful 3 bedroom/2 bathroom home located directly on Eel Creek. Appreciate the natural beauty of Chincoteague Island with gorgeous nature views from both the lower level screened in porch as well as the balcony off of the master suite. Enjoy relaxing mornings with the sunrise and breeze filled...

Sea Heart and Soul next to Sea Adventure and Soul are 2 miles from Assateague Island and 5 miles from beach front fun. AT $229.00 per night this Rental offers open spaces, a cozy, clean and comfortable place to stay along with amazing adventures for everyone to explore. Located just minutes from...

SEA ADVENTURE next to Sea Heart and Soul are 2 miles from Assateague Island and 5 miles from beach front fun. At $229.00 per night this Rental offers open spaces, a cozy, clean and comfortable place to stay along with amazing adventures for everyone to explore. Located just minutes from Assateague...

ANOTHER DAY IN PARADISE CHINCOTEAGUE BEAUTIFUL BAY FRONT CONDO WITH AMAZING WATER VIEWS Owner operated by: Annie Switzer Call 240/498/0074 *** Booking Fall 2018 & Beyond *** PLEASE CONTACT ME BEFORE BOOKING SUMMER 2019 Unit 103 - 'Another Day in Paradise' Unit 213 - 'Sunset in Paradise' 2nd...

Duck's Delight is our home in America's Happiest Seaside Town (2014 Coastal Living)! Entire home updated/renovated for the 2015 booking season! 4 bedroom (3 queen sized beds and 2 sets of bunkbeds), 2 bath Cape Cod in Chincoteague, VA., home of the Assateague ponies. Small fishing town on the...

***6242 Church Street*** Proud 3 story Traditional home located at the edge of town is rich in detail and history of the island. Beautiful renovations make this home just right for the whole gang. Just a few steps and walk to shopping and waterfront downtown plaza. Spacious rooms and large...

****5303 Meadow Drive**** Well appointed rancher in Piney Island, with large screened porch and private den with sleep sofa. Offers and water access!! Recently added all new appliances and floors for 2015 season. Very close to Assteague Island.*** Bed Sizes: 2 Queen, 2 Twin, 1 Queen Sleep...

****6300 Church Street **** Affordable vacation rental in historic downtown Chincoteague. Walk to shops, restaurants, fishing pier, waterfront park and farmers market. First floor bedroom, both bathrooms downstairs. Enjoy the back screened porch after the beach or relax in the front porch swing....

Epiphany on Deep Hole Creek. Deep Hole Creek Vacation Rentals Member, Chincoteague Chamber of Commerce Pets subject to approval and an additional fee. See DeepHoleCreek s ite for more info and photos.! Scroll down to email Blair & Martha (owners) . Or Call Blair & Martha at the number listed for...

***3400 Ridge Road*** Lovely 2 Bedrooms, 1.5 Baths duplex with water views. This duplex overlooks Assateague Island with great views for the Pony Swim. This is the Best way to watch the Pony Swim and not move from your porch! Sit and enjoy the views from 2 porches. The screened porch is off of the...

***6402 Teal Lane*** The unobstructed view of Eel Creek and Little Oyster Bay will get your attention at sunrise and sunset! Put your kayak in the water at the shared dock at high tide. Now has WiFi and 42' TV*** This Property accepts Weekly Rentals Only.*** Bed Sizes: 2 Queen, 1 Bunk Bed...

Enjoy the best of both worlds...Bay, Beach and Ocean by day and camp fire by night with air-conditioned / heated space to escape the elements when needed. Our home is comfy & cozy-newly built 1300 Square foot 2 story air-conditioned/heated home with 3 bedrooms to include 1 king sized bed, 1 queen...

***6314 Cropper Street*** Lovely renovated 3 story Victorian combines classic charm with affordable luxury located in the heart of downtown Chincoteague.*** Bed Sizes: 2 Queen, 2 Twin*** Prime Season Rates: $1000 weekly/$200 nightly. Off Season Rates: $800 weekly/$160 nightly. Additional...

***6204 Poplar Street*** Island Cottage has a great in town location! Easy walk to historic downtown's shops and retaurants. Perfect for a budget frienldy vacation. Has Wi-Fi.*** This Property accepts Dogs 35lbs and Under Only.*** Bed Sizes: 1 Queen, 1 Double, 1 Twin.*** 2019 Prime Season...

***4379 Ridge Road*** Lovely 2 bedroom home conveniently located on Ridge Road, not far from Maddox Blvd, with many great island attractions. Perfect house for a family of 4! This house offers extra space in the large sunroom. Bright and airy, the sunroom works for both cool and warm weather. The...

***4150 Grumpy's Lane*** Charming cottage located on a quiet, private lane. Close to town. Spacious sunroom addition! Newly added outside shower!*** Bed Sizes: 1 Queen, 1 Double Sleep Sofa*** 2018 Rates: Off Season Rates: $400 weekly/$80 per night. 2019 Rates: Prime Season Rates: $595...

***4473 Deep Hole Road*** This wonderful duplex has all the amenities you'd want including LOCATION!! Just off Maddox Blvd., you have easy access and can walk to everything! ***Electric Grill*** Bed Sizes: 1 Queen, 1 Twin Daybed w/Trundle, 1 Queen Sleep Sofa*** Prime Season Rates: $795...

Beautiful cottages located in the heart of Downtown Chincoteague with views of the Chincoteague Channel and Bay. The Key West Cottages are equipped with full kitchens, cozy living rooms, Queen bedrooms and large tiled showers. Amenities such as an indoor pool, hot tub and outdoor pool next door...

***4312 Main Street*** Enjoy the water view from this immaculate home offering spacious rooms and a quiet location off Main Street. All bedroom on the same level.*** Bed Sizes: 3 Queen, 1 Double Futon*** Prime Season Rates: $775 weekly/$155 per night. Off Season Rates: $600 weekly/$120 per...

***6559 Church Street*** Island home with large back yard and deck and Internet. Pet Friendly! Nearby is Chincoteague Crossing. 2 bedrooms and 2 baths downstairs/2 bedrooms upstairs.*** Bed Sizes: 1 Queen, 1 Double, 4 Twin*** Prime Season Rates: $795 weekly/$159 per night. Off Season Rates:...

***3702 Main Street**** Lovely victorian home with new open front porch and large well-appointed rooms. Newly renovated 2 full bathrooms. Newly installed hardwood floors. Also offering wireless internet! Walking distance to town and carnival grounds. Located across from Chincoteague Bay and near...

Leave all of your worries behind when you stay at this marvelous 3-bedroom, 2-bathroom Chincoteague Island vacation rental house! Boasting a year-round Florida room, space to sleep 8 guests, water views and a secluded canalside location with private pier, this quaint trailer-style property will...

***7200 Fiddler Bay*** Very nice waterfront townhome with remodeled chef's kitchen. Spectacular vistas of Assateague Island. Perfect spot for kayaking. 2 bedrooms and 2 baths upstairs (includes master bed and bath), half bath downstairs*** Bed Sizes: 1 Queen, 2 Twin, 1 Futon *** Prime Season...

***6312 Clark Street**** Island home renovated for your comfort. Close to town and Maddox Blvd. Back screened porch and second level loft sleeps the gang! With internet!*** Bed Sizes: 1 Queen, 1 Double, 4 Twin*** 2019 Prime Season Rates: $775 weekly/$155 nightly. Off Season Rates: $550...

***3584 Willow Street*** Pet Friendly, charming restored island home will make you smile! Relax in the screened porch after a day at the beach. Close to everything! A Short walk to the carnival and historic downtown with shops and restarurants. Large yard, perfect for children and pets. Close...

***4265 Pension Street*** Charming, traditional island home near town. Walking distance to shops, restaurants, and waterfront. Perfect for gathering family/friends!! Near Cattail Cottage, Miss Niccies, Time Out, and Rhinos Retreat. 4 bedrooms upstairs/2 baths downstairs. Bed Sizes: 1 Queen, 2...

***7141 Wayne Road*** Welcome to Blue Pearl Cottage, a lovely, sunny beach house, just minutes from fabulous beaches, wildlife and the quaint downtown of Chincoteague. This airy cottage nestled beside pine woods has a large wrap-around deck, a screened porch and offers privacy and quiet, with all...

***3849 Main Street*** Charming and spacious island home offering a first floor bedroom and Outside Shower. Close to center of town, near restaurants, shopping and nightly entertainment.***1 Bedroom & 1Bath downstairs/3 Bedrooms & 1 Bath-2nd floor/1 Bedroom-3rd floor.*** 20 Foot Boat slip rentals...

***3402 Ridge Road*** Lovely 2 Bedrooms, 1.5 Baths duplex with water views. This duplex overlooks Assateague Island with great views for the Pony Swim. This is the Best way to watch the Pony Swim and not move from your porch! Sit and enjoy the views from 2 porches. The screened porch is off of the...

SEA HARBOR: 1 mile from Assateague Island and 5 miles from beach front fun. Check-In 4pm Check-Out 12pm. This home offers large open spaces, a cozy, clean and comfortable place to stay along with amazing adventures for everyone to explore. It is furnished with many necessities so you can rest,...

***3545 Willow Street*** Very nice, comfortable 2 BR home will delight you with it's updated kitchen and new appliances. The large screened-in back porch with gas grill. Deck will accommodate outdoor entertaining. Centrally located, it is a short walk to town/shopping and the carnival grounds. 3...

New Chincoteague rental with panoramic views of Asseteague Island, ponies and lighthouse. Enjoy sunsets, crab, fish, swim, and kayak from shared dock with optional boat slip. 2 bedrooms (full and 2 twin bunks) (queen) pullout queen couch in living room. One full bathroom. Newly renovated with new...

***5277 Oyster Court- Oyster Bay I*** Oyster Bay I home will delight you with it's spacious bedrooms and lovely back sunroom. Small screen porch in front and a fish cleaning table belo, the home is set-up to enjoy. Offers wireless internet and satelite tv.*** Bed Sizes: 2 Queen, 2 Twin, and 1...

***6248 Ocean Boulevard*** Walk to restaurants, shopping, etc. from this in town home. Nearby is Atlantic Delight and A Sea Change. WiFi Available. Upstairs offers a master suite with a private bathroom and 2 bedrooms and a full bath. 1/2 bath downstairs.*** Bed Sizes: 1 Queen, 4 Twin*** Prime...

***6404 Pine Drive-Piney Island*** Nature lover’s dream! Tucked away in Piney Island with Assateague just a short bike ride away . You’ll love relaxing in the large screen porch or enjoy the water views from the second level deck. Community boat launch great for kayakers. Sleeps 9, screen porch,...

***5323 N. Hibiscus Drive-Oyster Bay II*** This spacious pet friendly home is located in the private community of Oyster Bay II. Enjoy your morning coffee from the large deck or screened porch. Wildlife abounds with deer, rabbits, ducks, geese, and lots of songbirds in this quiet retreat! Enjoy...

***6303 Chester Park***** Well appointed home located in quiet neighborhood offers first floor bedroom and bath. Offers internet access!*** Bed Sizes: 2 Queen, 2 Sets of Bunks(1 Twin & 1 Double on each)*** Prime Season Rate: $975 weekly/$195 nightly. Off Season Rates: $625 weekly/$125 nightly....