Southampton vacation rentals—beautifully furnished, luxury homes

The Southampton History Museum anchors village heritage across several beautifully kept sites, from the Rogers Mansion museum complex to the 1680s Halsey House & Garden, the working Pelletreau Silver Shop, and Conscience Point’s historic landing and nature walk. Expect compact, well-curated exhibits, seasonal tours, and programs that make local history feel close—architecture, decorative arts, maritime stories, and quiet gardens within a few elegant minutes of Main Street. Check the calendar before you go; select interiors and exhibitions rotate with restoration and events. Visit Southamptom History Museum

Southampton Arts Center is the village’s polished hub for exhibitions, film, performance, talks, and community programs. Expect free gallery admission, and an easy, walkable visit you can pair with boutiques and a late lunch. Check what’s on before you go; shows and events turn over frequently. Visit Southampton Arts Center

A family-owned Long Island standby with two locations—its Normandy chateau–style flagship in Water Mill and a North Fork outpost in Southold—pouring a broad range from Merlot and Chardonnay to distinctive bottlings like Pinot Meunier, Vidal ice wine, and a blueberry port. Tastings are relaxed and straightforward with indoor–outdoor seating and easy access off Montauk Highway or the Wine Trail. A polished, unfussy stop to add a flight and a few bottles to your Hamptons day. Visit Duck Walk Vineyard

The only Native American–owned and –operated museum on Long Island, presenting over 10,000 years of Shinnecock history through artifacts, exhibits, and seasonal programs. Built of Adirondack white pine and set on the reservation, it pairs galleries with outdoor cultural spaces and community events—the perfect way to understand where you’re visiting. Visit Shinnecock Cultural Center & Museum

Try your hand at surf fishing in front of the oceanfront dunes on this barrier beach. It’s a favorite spot for scenic picnicking and outdoor enthusiasts. Visit Shinnecock East County Park

Flying Point Beach in Water Mill is a scenic Southampton Town ocean strand—dunes and soft sand fronting the Atlantic, with Channel Pond just behind for a quiet backdrop. A polished, low-key choice for long walks and unhurried swims. Visit Flying Point Beach

Attend summer concerts or relax at the pond in this scenic park at the heart of village gatherings and community events. Visit Agawam Park

Hank’s Pumpkintown is a polished fall outing—apple and pumpkin picking paired with three interactive corn mazes and 30+ farm attractions, from wagon and tractor-train rides to giant slides and playgrounds. Expect a busy-but-well-run scene with a market for cider donuts, pies, and roasted corn, plus special events on weekends. Visit Hank's Pumpkintown

Relax over Italian coffee and pastries in a luxurious setting reminiscent of European cafes. Visit Sant Ambreous Southampton

75 Main is Southampton’s see-and-be-seen Main Street dining room—day-to-night energy, polished service, and a menu that leans Italian/New American (seafood, steaks, salads, brunch, and late cocktails). The scene is lively and hours stretch from morning espresso to a midnight close in season. A reliable stop when you want a spirited room steps from village shopping and the Parrish. Visit 75 Main

Savor the taste and aroma of quality coffee brewed from freshly roasted beans in a community-oriented and warm environment. Visit Hampton Coffee Company

Fivestory is a quietly luxe multi-brand boutique bringing its Upper East Side sensibility to Southampton—think impeccably edited womenswear, fine jewelry, accessories, and home pieces, with personal styling on request. It’s the right stop for a perfect shirt, a travel-ready set, or something special for dinner. Visit Fivestory NY

Shop for distinctive furnishings with stylish accents at the oldest department store in America. Visit Hildreth's

alice + olivia brings polished-playful aesthetic to the Hamptons—tailored blazers and trousers, statement minis, fluid maxi dresses, luxe knits, and event-ready sets in saturated color and refined prints. The boutique offers a calm, well-edited try-on experience with on-the-spot styling, so you can pull a dinner look or an entire weekend wardrobe in one stop. Visit alice + olivia