Cozy Winter Getaways Near Southampton, NY

Winter in the Hamptons has a charm all its own. With summer crowds gone and fireplaces glowing in historic inns, cold-weather weekends become the perfect excuse to slow down, unwind, and rediscover the quieter side of the East End. Whether you’re craving a romantic escape, a peaceful reset, or a short staycation without leaving home turf, there are plenty of cozy winter getaways near Southampton that fit the mood. From boutique inns with crackling fireplaces to waterfront retreats where the ocean sets the soundtrack, these spots make winter feel like a season to savor. Best of all, every destination on this list is open to the public and within about a 30-minute drive of Southampton, making spontaneous winter escapes easy to plan.

The Southampton Inn (Southampton)

Sometimes the coziest getaway is right in town, and the Southampton Inn proves that you don’t need to go far to feel transported. This classic property offers warm, comfortable rooms and a relaxed atmosphere that feels especially inviting during the winter months. The quieter season means fewer guests, more personalized service, and a chance to truly enjoy the peaceful side of Southampton Village. Winter rates are often more flexible, making it a great choice for a quick overnight reset or weekend staycation. You can explore room options and seasonal specials at the Southampton Inn. It’s perfect for locals who want a break without leaving familiar surroundings behind.

Topping Rose House (Bridgehampton)

If your idea of cozy includes luxury with a rustic twist, Topping Rose House in Bridgehampton is hard to beat. This historic mansion-turned-boutique-hotel blends elegant design with warm fireplaces and a serene countryside setting. Winter is a particularly special time here, when the property feels more intimate and the spa becomes an irresistible cold-weather retreat. Guests love lingering over long dinners and waking up to frosty mornings in plush robes. To browse accommodations and spa offerings, visit Topping Rose House. It’s a winter escape that feels indulgent without being over the top.

Baron’s Cove (Sag Harbor)

Overlooking the harbor in Sag Harbor, Baron’s Cove delivers cozy waterfront vibes that shine in the off-season. With fireplaces, water views, and an on-site restaurant known for comfort-driven menus, it’s an ideal spot for a romantic winter weekend. The village itself becomes wonderfully walkable in winter, letting you browse shops and galleries without crowds. Many rooms feature balconies or patios, perfect for enjoying crisp air with a hot coffee in hand. You can explore seasonal packages and availability at Baron’s Cove. It’s the kind of place that makes you linger longer than planned.

The Baker House 1650 (East Hampton)

For a getaway that feels like stepping into another century, The Baker House 1650 in East Hampton offers historic charm paired with modern comfort. This elegant bed and breakfast is known for its fireplaces, spa tubs, and warm hospitality that’s especially inviting during winter. Guests often rave about quiet mornings, candlelit evenings, and indulgent breakfasts that set the tone for relaxed days. Winter weekends here feel slower, more intimate, and perfectly suited for couples seeking downtime. You can view rooms and winter availability at The Baker House 1650. It’s a timeless escape that turns cold days into something to look forward to.

The Roundtree Amagansett (Amagansett)

If privacy and understated luxury top your list, The Roundtree Amagansett offers a peaceful winter refuge just east of Southampton. This boutique property features cottage-style accommodations, fireplaces, and beautifully landscaped grounds that feel serene even in colder months. Winter guests enjoy quiet evenings, personalized service, and the sense of having the place almost to themselves. It’s an excellent choice for couples or solo travelers looking to unplug and recharge. To explore winter stays and amenities, visit The Roundtree Amagansett. It’s cozy, refined, and wonderfully calming.

Mill House Inn (East Hampton)

For travelers who appreciate thoughtful details and home-like comfort, the Mill House Inn in East Hampton delivers a warm, welcoming winter experience. This boutique inn is known for its attentive service, gourmet breakfasts, and relaxed atmosphere that feels perfect for cold-weather escapes. Winter brings a quieter pace, letting guests fully enjoy nearby beaches, shops, and trails without the bustle. The rooms themselves are designed for comfort, making evenings in just as appealing as outings. You can learn more about seasonal stays at the Mill House Inn. It’s ideal for those who want refined comfort with a personal touch.

Sag Harbor Inn (Sag Harbor)

Tucked into the heart of Sag Harbor Village, the Sag Harbor Inn offers cozy charm with easy access to shops, restaurants, and the harborfront. Winter stays here feel especially intimate, with fewer guests and more opportunities to enjoy the village at your own pace. The inn’s classic rooms and welcoming vibe make it a great base for exploring or simply relaxing with a book by the window. Many guests love strolling the docks in winter, when the harbor feels calm and reflective. To check availability and winter specials, visit the Sag Harbor Inn. It’s a simple, stylish escape that captures the essence of off-season Sag Harbor.

Wrap-up: winter escapes worth savoring

Winter in Southampton and the surrounding Hamptons offers a quieter, cozier version of the East End—one filled with fireplaces, peaceful villages, and beautifully relaxed weekends. Whether you’re drawn to historic inns, waterfront retreats, or boutique hideaways, these cozy winter getaways near Southampton prove that cold weather can be just as magical as summer. Each destination offers its own version of warmth, comfort, and charm, all within an easy drive from home. Keep this list handy for snow days, anniversary weekends, or those moments when you simply need a change of scenery. And as you plan your next seasonal escape, don’t forget that a smooth, comfortable drive sets the tone for the whole trip—Mercedes-Benz of Southampton is a trusted local partner when you’re ready to travel in style this winter.