If you're going to be staying for a week or more, you might want to consider renting a cottage or house—an arrangement that gives you a chance to settle in and get a real taste of island living. Many visitors, especially those with children, find renting more relaxing than staying in a hotel or an inn. With your own kitchen, you'll save money by eating in; plus you can enjoy such homey summer pleasures as barbecues. Though decor can vary from chichi to weatherworn, most cottages come equipped with all you'll need to ensure a comfortable stay. Steer clear of a house without linens; it's a sign of bad things to come. The better houses come fully accoutered: not just with basics but with luxury touches like cable or satellite TV, a CD player, gourmet kitchen implements, beach chairs, and bikes.
Finding a great cottage or house can be tough, however, especially since so many are rented a year or more in advance by returning guests. The time to start your search is a summer ahead, though you can occasionally find a property as late as spring. A good way to shop is to stop in and visit Realtors when you happen to be in town. Be prepared for a bit of sticker shock, though. Prices are generally about twice what you'd have to pay on Cape Cod or even the Vineyard. In summer, very rustic (read shabby) rentals start at about $1,200 a week and can run to many times that ($3,500 and up) for multibedroom or waterfront properties.
Country Village Rentals (10 Straight Wharf. 508/228-8840 or 800/599-7368. www.cvrandr.com) knows its clientele, who like to flit to sweet spots like Stowe and St. Bart's. Lucille Jordan Real Estate (8 Federal St. 508/228-4449. www.jordanre.com) has a broad rental inventory; check the photos lining the storefront windows. The Maury People (35-37 Main St. 508/228-1881. 508/228-1481. www.maurypeople.com), associated with Sotheby's, has more than 1,000 private homes in its rental inventory, including historic and beach homes; service is not only knowledgeable but personable. Preferred Properties (76 Easton St. 508/228-2320 or 800/338-7715. 508/228-8464. www.preferredpropertiesre.com) is a Christie's affiliate whose offerings range "from cottages in the sand to castles on the cliff."