Find hotels in Westport, CT from CA $105

The best area to stay in Westport is the downtown area, particularly around Main Street and Post Road.This central district is the heart of Westport, offering a refined blend of upscale boutiques, art galleries, and diverse dining options. It's incredibly walkable, with the Saugatuck River winding through it, providing scenic views and opportunities for riverside strolls. You'll find everything from casual cafes to fine dining establishments here, alongside a well-curated selection of shops.For couples, downtown Westport provides an ideal setting for a relaxed and sophisticated getaway. You can enjoy an evening walk along the river, catch a show at the Westport Country Playhouse, or explore the various independent shops and art galleries, all within easy reach of quality accommodation.Families travelling with older children will also appreciate the convenience of downtown. The proximity to Compo Beach, just a short drive away, offers a pleasant day out by the water, while the numerous restaurants cater to different tastes.

The best time to go to Westport is during the warmer months, specifically from late spring (May) through early autumn (October), when the weather is most pleasant for enjoying outdoor activities and the town's coastal charm.May and June offer comfortable temperatures, usually in the low to mid-20s Celsius, making it ideal for walking around the town centre, exploring the shops along Main Street, or enjoying a meal at an outdoor cafe. The Saugatuck River is particularly inviting for boating or kayaking during this period, and many local events begin to kick off.July and August are the peak summer months, with temperatures often reaching the high 20s or even low 30s Celsius. This is great for spending time at Compo Beach, swimming in the Long Island Sound, or taking a scenic walk along the shoreline. Families will find plenty to do, from beach days to enjoying the numerous parks and playgrounds.September and October bring slightly cooler, crisp weather, typically in the high teens to low 20s Celsius, and beautiful autumn foliage, especially along the Merritt Parkway and surrounding residential areas. This is a great time for couples to enjoy a romantic getaway, perhaps with a scenic drive, a visit to a local farm, or a stroll through Sherwood Island State Park without the summer crowds.