Island Property manages the rental of well-maintained privately owned properties throughout the island. Though there are several rental companies, Island Property appears to manage the nicest properties which come in all sizes, locations, from "rustic" cabins to larger, elegant bayside homes. The staff at the rental office is very accomodating and professional.
Somewhat of a drag: rentals are generally Saturday to Saturday -- arrival by 3pm, check out by 11am. Garbage and recyclables aren't picked up at the rental home so you have to drop everything off on your way out of town at the waste management center.
Island Property has pictures for each property and search tool on their website based on what kind of home you are looking for (ie, number of bedrooms, location, equipment, etc). Islandprop.com. The site gives a pretty accurate rendering of what the properties actually look like - up-to-date photos, amenities listings, etc. We've selected and reserved our rentals based on reviewing the homes on the website.
"Watermark" is perfect for those who enjoy cooking as the home is equipped with nearly every kitchen gadget I have at home, good knives, pots and pans, etc. It is suprisingly well-furnished and styled with french-country prints and creative/pottery barn style furniture. Two bedrooms -- one loft style over the living room, and a more private room on the first floor. Both have their own bathrooms. The layout actually worked well for two couples. A big screened-in porch over looking a saltwater inlet has wooden furniture for lounging and dining. (Unfortunately, mosquitoes are a BIG nuisance in Chincoteague so if you want to spend time outside at nite, screens are necessities, or excessive protective coats of DEET are required).
Watermark is tucked away in a quiet area with just a few other homes. The inlet is great for crabbing and birdwatching. NB: It is a good 30 minutes bike ride to the beach.