Sag Harbor vacation rentals—beautifully furnished, luxury homes

The Custom House Museum is the preserved home and office of Henry Packer Dering—Sag Harbor’s early customs master and postmaster—interpreting the harbor’s role as a federal Port of Entry after 1789. Seasonal tours by Preservation Long Island lead through Georgian-era rooms, maritime exhibits, and new research that surfaces the lives of enslaved people who lived and worked in the house. Visit Custom House Museum

Sag Harbor Cinema is a nonprofit, state-of-the-art triplex on Main Street with a variety of programming—new releases, restorations and 35mm one-offs, filmmaker Q&As, and thoughtful community series—presented in a polished, walkable setting steps from the harbor. Visit Sag Harbor Cinema

Shop local produce, artisanal goods, and unusual crafts at this vibrant seasonal market, supporting local farmers and vendors. Visit Sag Harbor Farmer's Market

Mashashimuet Park is Sag Harbor’s central green space—with playgrounds, athletic fields, courts, and easy access to Otter Pond and the Long Pond Greenbelt. The park opens at 6 a.m. and winds down at sunset, keeping it ideal for a morning loop, a casual game, or a low-key afternoon outdoors. Visit Mashashimuet Park

Long Beach (Foster Memorial Beach) curves along Noyac Bay with calm, shallow water, soft sand, and a gentle entry that’s ideal for relaxed swims, paddleboards, and kid-friendly afternoons. West-facing sunsets here are wide and spectacular. It’s an easy beach day with big sky and smooth water. Visit Long Beach

Elizabeth A. Morton National Wildlife Refuge protects 187 acres on a peninsula between Noyack and Little Peconic Bays—bay beaches, marsh, ponds, and maritime forest that shelter migratory birds, shorebirds, and wintering waterfowl. Walk the easy Wild Birds Nature Trail to overlooks and a quiet stretch of sand; in nesting season, portions of the beach close to protect piping plovers and terns. Visit Elizabeth Alexandra Morton National Wildlife Refuge

Sag Harbor’s grand, old-world landmark on Main Street—an 1846 inn restored to quiet elegance with a white-tablecloth dining room and one of the world’s great wine lists. Expect classic service, a proper dress code, and meals from breakfast through late dinner; the cellar holds a long-running Wine Spectator Grand Award, making the room as much about the list as the plate. Reserve ahead, then linger over oysters, a martini, and something from the deep book in a setting that defines village poise. Visit The American Hotel

Le Bilboquet in Sag Harbor is a polished, harborside French dining room, known for white-tablecloth service, marina views, and a firm “dress to impress” code (no beachwear). Expect classics—oysters, Niçoise, Dover sole, the house Cajun chicken—and a lively terrace that feels made for golden hour over the docks. Reservations are essential, and the scene skews elegant from lunch through late. Visit Le Bilboquet

Grindstone Coffee & Donuts offers fresh brioche and cake donuts made in small batches with European-style butter and in-house glazes, plus properly pulled espresso. Flavors rotate (classics and limited runs), and the shop is open year-round, making it an easy morning stop before a harbor walk or beach day. Visit Grindstone Coffee & Donuts

The Shopping Cove is a tucked-away cluster of boutiques where you can slip from coffee and a newspaper to a haircut, then browse handmade clothing (including Indian textiles), chic jewelry, and design services—all within a few quiet steps of the harbor. Visit Sag Harbor Shopping Cove

Explore a wide range of toys, home decor, and children’s books. Visit The Wharf Shop

TWP is a refined womenswear boutique by designer Trish Wescoat Pound, offering impeccably made American sportswear—tailored shirting, polished suiting, elevated essentials, and luxe knits—rendered in fine Italian fabrics and produced in New York. Visit TWP