The 10 Best Boutique Hotels in Shelter Island (2025)

Nestled in the heart of Greenport, The Menhaden Hotel invites you to experience modern luxury intertwined with local charm. With its stunning rooftop terrace offering panoramic views of serene landscapes and bustling village life, this boutique hotel is a romantic haven for couples, adventure seekers, and wellness enthusiasts alike.

Rooftop Lounge & Bar - Unwind at our chic rooftop lounge, where each sunset paints the sky as you sip artisanal cocktails made from local ingredients, surrounded by the soft sounds of nature and gentle waves lapping nearby.

Sustainable Luxury - Embrace eco-conscious living with our thoughtfully curated amenities, from organic bath products to complimentary electric bike rentals, allowing guests to explore the scenic beauty of Long Island while reducing their carbon footprint.

Culinary Delights - Indulge your culinary curiosity with self-service breakfasts featuring warm croissants and delightful teas, complemented by a cozy cafe stocked with local snacks that invite you to savor every moment during your stay.

Guest Experiences - As you stroll through the inviting lobby filled with artful decor, the scent of freshly baked cookies wafts through the air, creating a comforting ambiance. Guests have often found themselves lingering at the front desk, captivated by the staff’s genuine warmth and personalized recommendations that feel like they’re part of the family.

Nestled at the water's edge in the charming village of Sag Harbor, Baron's Cove is a luxurious retreat that effortlessly marries modern elegance with coastal charm. From the moment you step into its thoughtfully designed interiors, the air is infused with the salty breeze of the sea, beckoning you to unwind in an atmosphere that feels both intimate and rejuvenating.

Romantic Oasis - With rooms that open onto private gardens and stunning sea views, every corner of Baron's Cove whispers romance. Imagine waking up to the gentle sound of waves lapping at the shore as you sip your morning coffee wrapped in the embrace of a plush bathrobe.

Culinary Delights - The on-site restaurant offers a taste of fresh American cuisine crafted with local ingredients, inviting you to savor delightful meals that nourish both body and soul. The cozy bar, complete with a crackling fireplace, becomes a beloved spot for evening relaxation after a day spent exploring.

Total Relaxation - Dive into the seasonal saltwater pool or take a leisurely stroll to nearby beaches, where free passes await you. This hotel is more than just a place to stay; it’s a sanctuary for wellness enthusiasts seeking tranquility amid natural beauty.

Guest Experiences - One guest relished the cozy ambiance of the hotel’s lounge, describing the comforting aroma of freshly brewed coffee wafting through the air as they sank into a plush chair by the fireplace. Another noted the unexpected joy of their room’s garden, where morning sunbeams danced upon petals, creating a serene escape right outside their door.

Nestled in the heart of Bridgehampton, Topping Rose House offers a serene escape infused with elegance and rustic charm. With its picturesque landscape defined by sprawling gardens and an air of intimacy, this upscale retreat invites couples and wellness enthusiasts alike to indulge in luxurious relaxation and culinary delights sourced directly from the hotel's own farm.

Spa Breaks - Experience rejuvenation at the on-site spa, where soothing scents fill the air and skilled therapists offer personalized treatments designed to melt away stress and tension.

Foodies - Savor each bite at the farm-to-table restaurant, where the melody of fresh ingredients blends harmoniously with seasonal flavors, creating an unforgettable dining experience that celebrates local bounty.

Romantic Break - Whisk your loved one away to beautifully appointed rooms adorned with Frette linens; here, intimate moments unfold against a backdrop of tranquil views and impeccable design.

Guest Experiences - One guest marveled at the serene ambiance, noting how the soft crunch of gravel underfoot and the sweet aroma of herbs from the garden mingled, creating an oasis of calm that lingered long after their visit.

Nestled amidst five acres of meticulously manicured grounds in the heart of Southampton, the Southampton Inn offers a serene escape infused with elegance and charm. From the moment you arrive, the intoxicating scent of blooming flowers dances on the summer breeze, inviting you to unwind in an oasis where every detail is crafted for your delight.

Romantic Getaways - With its intimate ambiance and enchanting gardens, Southampton Inn is the perfect setting for couples seeking a romantic retreat. Enjoy leisurely afternoons beside the shimmering outdoor pool or take advantage of our complimentary shuttle to nearby Coopers Beach, where sunsets paint the sky in hues of pink and gold.

Culinary Delights - Indulge in culinary artistry at Claude's, where each dish is a celebration of fresh, local ingredients. Whether savoring a delightful brunch in the courtyard or cozying up for dinner in the stylish dining room, guests are treated to flavors that evoke the very essence of coastal living.

Wellness & Relaxation - Rejuvenate your spirit in our tranquil library or enjoy spirited matches on the tennis court, all while surrounded by lush landscapes. The soothing atmosphere encourages relaxation and mindfulness, whether you prefer lounging poolside with a good book or indulging in leisurely strolls through the estate’s scenic paths.

Guest Experiences - One guest recounted the joy of returning to their pristine room after a day at the beach, where the soft linens and inviting aroma of freshly brewed coffee made them feel right at home. Many noted the charming fireplace in the lobby, a warm gathering spot where friendly staff offered personalized recommendations, making each visitor feel like part of the family.

Nestled in the enchanting embrace of East Hampton, Journey East Hampton invites you to escape into a world where modern luxury meets the serene charm of coastal living. With whispers of the ocean breeze and the promise of tranquil getaways, this boutique hotel is an idyllic haven for couples, wellness enthusiasts, and cultural explorers alike, all seeking a touch of elegance amid nature's beauty.

Boutique Beach Life - Experience a chic blend of modern design and coastal allure just moments from Indian Wells Beach, where each room’s soothing palette and stylish furnishings echo the nearby sands and sea, creating an oasis of relaxation.

Romantic Breaks - Unwind with your special someone as the sun sets over the horizon, complemented by evenings around the fire pit, where the aroma of roasting s'mores mingles with gentle laughter—the perfect recipe for cherished memories.

Active Holiday - Explore the picturesque surroundings on complimentary bikes, breezing along scenic paths and making spontaneous stops at local markets—where fresh produce and artisanal goods beckon with colorful splendor.

Guest Experiences - As you step into the lobby, the inviting scent of freshly brewed coffee envelops you, while the warmth of the staff's genuine smiles makes it feel like home away from home. Even the soft cotton sheets cradle you into a peaceful slumber after a day filled with adventure.

Nestled in the charming Village of Amagansett, The Roundtree is a hidden gem where modern luxury meets rustic charm. This exquisite retreat envelops you in an atmosphere of tranquility, offering intimate hideaways and meticulously designed spaces that beckon guests to unwind, explore, and indulge in life's simple pleasures.

Total Relaxation - Experience pure serenity as you sink into plush furnishings surrounded by lush gardens and fragrant blooms. The gentle rustle of leaves and the soothing scent of fresh air create an idyllic escape from the everyday hustle.

Romantic Break - With cozy separate cabins and thoughtfully curated decor, each moment feels like a personal love letter to romance. Perfect for couples seeking privacy, this enchanting setting invites whispered conversations against a backdrop of soft candlelight.

Boutique - Every corner of The Roundtree tells a story, adorned with unique artworks and curated treasures. The blend of contemporary design with local character creates a warm, welcoming ambiance that feels both luxurious and intimately familiar.

Guest Experiences - One guest noted the delightful surprise of finding complimentary snacks and aromatic Nespresso coffee waiting in their cabin, making mornings feel indulgent. Evenings transformed into magical moments as they gathered around the crackling bonfire, sharing laughter and stories under a canopy of stars.

Nestled in the heart of historic Essex, Connecticut, The Griswold Inn is a charming escape that effortlessly blends timeless elegance with contemporary comfort. Here, the air is rich with the scent of freshly brewed coffee and homemade breakfasts, while the sound of laughter fills the cozy lounges and the warm glow of candlelight beckons you to unwind beneath the exposed beams of this storied inn.

Historic Charm - As the oldest continuously operating tavern in Connecticut, The Griswold Inn boasts an enchanting ambiance filled with stories from yesteryear. Each corner whispers tales of travelers who once gathered here, offering a unique blend of nostalgia and luxury that's palpable in every detail.

Culinary Delights - Savor culinary creations that celebrate local flavors in the inn's elegantly appointed restaurant, where American cuisine meets attentive service. The breakfast spread is fresh and vibrant, featuring nutritious options that awaken the senses, ensuring guests start their day on a delightful note.

Intimate Atmosphere - With its inviting garden, chic shared lounge, and a tranquil terrace, The Griswold Inn provides serene spaces for relaxation or intimate conversations. The soft rustle of leaves and gentle hum of nearby conversations create an atmosphere that feels both exclusive and welcoming.

Guest Experiences - One guest fondly recalled the feeling of being embraced by the inn's history as they enjoyed live music in the Tap Room, where the aroma of hearty dishes mingled with laughter. Although the room was snug, the plush bed enveloped them in comfort, making it a cozy retreat after a day exploring nearby sights.

Nestled along the picturesque shores of Long Island Sound, Madison Beach Hotel, Curio Collection by Hilton is a sanctuary of elegance and tranquility. With its private beach access and charming coastal ambiance, this upscale retreat invites couples and honeymooners to indulge in romance while soaking in the breathtaking views of glistening waters and vibrant sunsets.

Romantic Escape - Immerse yourself in an intimate atmosphere where every detail, from plush room furnishings to soft lighting, sets the stage for romance. Whether lounging on the beach or savoring a candlelit dinner at the full-service restaurant, every moment here feels like a cherished secret shared between lovers.

Total Relaxation - Unwind in your spacious room, where serene sea views wash over you, creating a perfect backdrop for relaxation. The gentle sound of waves lapping against the shore will lull you into a state of bliss, encouraging you to leave behind the stresses of everyday life.

Spa Breaks - Rejuvenate your senses with luxurious spa treatments designed for ultimate indulgence. Feel the tension melt away as skilled therapists work their magic, leaving you refreshed and revitalized, ready to embrace the beauty of Madison’s tranquil surroundings.

Guest Experiences - As one guest recounted, they found themselves mesmerized by the stunning view from their room, where the horizon blended effortlessly with the colors of sunset, painting a picture perfect enough to rival any postcard. Even amidst a stormy day, the serene atmosphere enveloped them, making it easy to forget the world outside.

Nestled along the stunning shores of Montauk, Gurney's Montauk Resort & Seawater Spa offers a tranquil escape where luxury meets the rhythmic whispers of ocean waves. The air is imbued with a blend of salty breezes and the soothing scent of seawater, creating an intimate ambiance perfect for couples seeking romance or serenity seekers yearning for revitalization.

Total Relaxation - Indulge in holistic wellness at the ocean-fed seawater spa, where healing treatments and rejuvenating experiences await. Let the sound of gentle waves lull you into tranquility as you immerse yourself in the warm embrace of the indoor pool.

Romantic Break - Each room is a serene sanctuary offering breathtaking ocean views that capture both sunrise and sunset; the soft crash of the surf becomes your backdrop for idyllic evenings spent together, enhancing every moment of your romantic getaway.

Spa Breaks - Revel in the luxurious pampering provided by Gurney’s dedicated staff, whose attentive service ensures every detail—from personalized treatments to lounging in the sauna—is perfectly curated for an unforgettable retreat.

Guest Experiences - Guests rave about the inviting decor, noting how the fresh ocean air mingles with hints of sea salt, transporting them to a serene paradise. Families delight in the cozy one-bedroom apartments where laughter echoes off the walls, and children joyfully splash in the indoor pool, while parents unwind in the exquisite bathhouse.

Nestled in the serene embrace of Quogue, The Quogue Club invites you to indulge in a luxurious retreat where modern elegance meets intimate charm. With whispers of the ocean breeze and the gentle rustling of trees, this boutique haven promises an unforgettable getaway for couples and adventure seekers alike, all while surrounded by exquisite decor that captivates the eye at every turn.

Romantic Break - Rekindle love amidst charming surroundings, where candlelit evenings and plush bedding create the perfect backdrop for romance. The subtle scent of fresh blooms fills the air, enhancing those quiet moments spent together over a carefully curated selection of wines.

Spa breaks - Unwind with rejuvenating treatments that pamper your senses, from soothing massages to invigorating facials. Immerse yourself in a tranquil oasis as scents of eucalyptus and lavender envelop you, leaving behind the cares of everyday life.

Local exploring - Discover the rich tapestry of Quogue’s local culture, from quaint shops bursting with artisan crafts to vibrant markets brimming with fresh produce. Each stroll reveals hidden gems waiting to be explored, inviting you to savor the essence of this coastal town.

Guest Experiences - One guest fondly recalled waking up to the aroma of freshly brewed coffee wafting through the halls, blending seamlessly with the warmth of sun-kissed walls. While some rooms might feel cozy, the breathtaking décor and attentive staff ensure that even the smallest spaces feel like a sanctuary.