The 16 Best Boutique Hotels with Entertainment in Long Island (2025)

Nestled along the serene shores of Port Washington, Fathoms Hotel & Marina invites you to experience a perfect blend of modern luxury and waterfront tranquility. Every sunset paints the sky in hues of orange and lavender, casting a magical glow over your intimate escape, where personalized service and charming details create a truly unforgettable setting for romance or relaxation.

Waterfront Tranquility - Breathe in the fresh sea air as gentle waves lap against the marina, offering you a peaceful retreat. Whether you're sipping cocktails on the terrace or enjoying a quiet moment in your room, the soothing sounds of nature envelop you like a warm embrace.

Chic Accommodations - Each beautifully designed room is a sanctuary, featuring plush bedding and tasteful decor that evokes comfort and sophistication. Feel the cool breeze through open balcony doors, inviting you to unwind and revel in the stunning views just outside.

Culinary Delights - Indulge your palate at the onsite bar, where expertly crafted cocktails and gourmet snacks await. The atmosphere buzzes with laughter and the clinking of glasses, creating a vibrant social scene that complements a delightful evening by the water.

Guest Experiences - As dusk settles, the hotel transforms into a haven of warmth, where Cindie and Steve's attentive hospitality shines through. Guests speak of lingering moments—like sinking into a comfortable chair, wrapped in a cozy throw while savoring the salty scent of the ocean breeze, all while watching the sun dip below the horizon.

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 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 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.

Nestled in the serene embrace of Woodbury, The Inn At Fox Hollow Hotel invites you to indulge in a luxurious retreat where sophistication meets comfort. Picture yourself wandering through lush gardens under a canopy of whispering trees, returning to an elegant suite that feels like your own private sanctuary, complete with a fully equipped kitchen and a cozy ambiance designed for relaxation.

Total relaxation - Unwind by the sparkling outdoor pool or luxuriate in the tranquil courtyard, where the sweet fragrance of blooming flowers dances on warm breezes, creating an idyllic setting for intimate conversations or peaceful solitude.

Foodies - Savor mouthwatering Italian dishes at the award-winning Volpe Restaurant, where each bite is a celebration of flavors, or delight in the complimentary weekday dinners that turn every evening into a culinary adventure, complete with the aroma of freshly prepared meals wafting through the air.

Spa breaks - Indulge in moments of bliss with soothing spa-like amenities, including a well-appointed fitness center and inviting hot tubs that beckon you to immerse yourself in warmth while enjoying gentle music that calms the senses.

Guest Experiences - Imagine the friendly laughter echoing in the hallways as staff members go out of their way to ensure your stay is exceptional—like the charming shuttle drivers who not only whisk you away but also share stories of local treasures, making each ride feel like a delightful conversation with a friend.

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 just moments from the pristine shores of Montauk, The Montauk Beach House invites you into a chic coastal retreat where modernity meets relaxed elegance. Imagine unwinding by a shimmering pool with refreshing cocktails in hand as the soft sounds of live DJ music set the perfect backdrop for romance and relaxation.

Beach Life - Dive into the quintessential Montauk experience with effortless beach access, where sun-soaked days blend seamlessly into balmy evenings spent strolling along the shore, soaking up the coastal charm.

Boutique - Discover an alluring mix of style and comfort in our uniquely designed accommodations, featuring airy spaces that boast stylish decor and thoughtful amenities to ensure your stay is both luxurious and intimate.

Spa breaks - Indulge in wellness with options for relaxation and rejuvenation at nearby spas, or simply unwind by the poolside, where the scent of blooming gardens mingles with the warm sun, creating a serene atmosphere.

Guest Experiences - As you sip on a perfectly chilled cocktail poolside, the gentle breeze carries hints of fresh sunscreen and sea salt, while attentive staff float by, ensuring your glass never runs dry—a blissful moment punctuated by the rhythmic beats of chill tunes and laughter echoing around the vibrant space.

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 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 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 in the heart of New Haven, Luxury Furnished Apartments by Hyatus Downtown at Yale offers an exquisite retreat where modern elegance meets the warmth of home. As you step into your private haven, the soft textures and warm hues invite you to unwind, while the faint scent of fresh coffee wafts through the air—setting the stage for a tranquil escape or a romantic getaway.

Romantic Retreat - Ideal for couples seeking intimacy, each apartment features cozy nooks and inviting spaces that whisper romance, making it perfect for early morning coffees on the balcony or candlelit dinners amidst chic decor.

Wellness Haven - Recharge in our fitness room with yoga classes designed to harmonize body and spirit, then indulge in the serene ambiance of our garden—a peaceful sanctuary where you can breathe deeply and let the day's stresses melt away.

Cultural Exploration - With Yale University just over a mile away, guests can immerse themselves in a vibrant tapestry of art, history, and culture, all within walking distance—perfect for spontaneous museum visits or leisurely strolls through historic neighborhoods.

Guest Experiences - One guest marveled at how the spacious apartment felt like a welcoming embrace, with plush furnishings and soft linens creating a sanctuary after a long day. They were pleasantly surprised by the thoughtful hospitality, as a staff member had left a handwritten note inviting them to explore local markets just around the corner.

Nestled in the vibrant heart of New Haven, the Omni New Haven Hotel at Yale beckons discerning travelers with its blend of modern elegance and rich cultural heritage. Just a leisurely stroll from the historic Yale University, this sanctuary invites you to indulge in a symphony of sophistication and comfort, where every corner whispers tales of art, academia, and adventure.

Outstanding Location - At the crossroads of history and contemporary charm, the hotel is perfectly positioned for those who wish to explore eclectic neighborhoods filled with museums, art galleries, and unique boutiques—all just steps away from your elegant abode.

Romantic Break - With chic interiors and intimate nooks, the Omni sets the stage for romance, where couples can unwind together after a day of local exploration or savor candlelit dinners at nearby restaurants that inspire culinary passion.

Spa & Relaxation Lovers - An oasis of tranquility, the hotel features state-of-the-art fitness facilities and invigorating spa treatments designed to rejuvenate the body and soul, making it an ideal retreat for wellness enthusiasts looking to recharge amidst their adventures.

Guest Experiences - As you enter, the welcoming scent of fresh coffee wafts through the lobby, mingling with the soft murmur of laughter from fellow guests. You might even catch the front desk staff sharing a warm smile or a tip about the best local spots—like that hidden gelato shop around the corner that transformed one guest's afternoon into a delightful escapade.

Nestled in the charming town of Fairfield, Hotel Hi-Ho invites you to bask in a serene escape where romance meets modern convenience. With its effortlessly chic ambiance and intimate atmosphere, this four-star haven is perfect for couples seeking a tranquil getaway or adventure lovers exploring Connecticut's coastal treasures.

Romantic Break - Indulge in secluded moments at Hotel Hi-Ho, where romantic decor and cozy nooks create an intimate setting. Picture soft candlelight illuminating your dinner at the on-site restaurant, Barcelona, while shared laughter fills the air, weaving memories that linger long after your stay.

Total Relaxation - Unwind in stylish accommodations boasting a contemporary flair, where generous beds invite you to sink deep into plush comfort. The gentle hum of nature outside lulls you into serenity, making it an ideal retreat for wellness enthusiasts and honeymooners alike.

Artworks - Explore the local cultural scene just minutes away, with the Housatonic Museum of Art nearby offering a feast for the senses. Immerse yourself in the beauty of local artistry that complements your experience at Hi-Ho, enhancing your journey through Fairfield’s vibrant tapestry.

Guest Experiences - Guests have noted the delightful contrast of quiet surroundings punctuated by the occasional distant rush of traffic, creating a unique backdrop for moments of reflection. Many appreciated the pristine cleanliness and modern touches of their rooms, creating a welcoming ambiance that felt like a home away from home.

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 in the charming embrace of West Hartford, Delamar West Hartford exudes an air of sophistication and warmth, captivating guests with its elegant design and attentive service. Whether you’re indulging in a tranquil spa day or savoring exquisite American cuisine at the on-site restaurant, every corner invites you to unwind and relish the luxurious ambiance.

Spa Retreat - Experience pure bliss at our indulgent spa, where soothing aromas mingle in the serene atmosphere, making each treatment feel like a personal escape into tranquility. Guests leave feeling rejuvenated, their cares washed away as they bask in the luxury of holistic wellness.

Romantic Hideaway - Whisk your partner away to a haven of intimacy with beautifully appointed rooms that echo romance, complete with plush furnishings and warm lighting. The hushed whispers of laughter and clinking glasses from the bar add to the intimate allure, setting the stage for treasured memories.

Outstanding Location - Situated just minutes from cultural gems like the Mark Twain House and vibrant Elizabeth Park, the hotel serves as your gateway to local exploration. Stroll through picturesque streets, where historic charm meets modern convenience, creating a backdrop for unforgettable adventures.

Guest Experiences - A recent visitor marveled at the spaciousness of their room, perfectly cozy with luxurious textures that beckoned after a long day of exploring. Meanwhile, the delightful scent of freshly brewed coffee wafted down the hallway each morning, accompanied by the cheerful banter of friendly staff, making guests feel right at home.