Vacation rentals in Head of the Harbor

The Suite at North shore LI

This unique place has a style all its own. We have created a combination of a peaceful atmosphere with a sophisticated touch. Few minutes away from Stony brook Hospital and University, and other educational and hospital destinations. Few minutes away to many of the best restaurants on the North Shore LI. And of course if you are visiting to just enjoy the Island, this is the perfect location to any desire destination like wineries, beaches and so many places this beautiful Island has to offer.

Cozy Modern Getaway

Cozy Modern Getaway in Centereach! Perfect for students, medical visitors, and travelers. Relax in a bright living area with 55” Smart TV+PS5, dine at a 2-seat nook, and cook in the well-equipped kitchen with refrigerator, microwave, coffee maker, popcorn machine, cookware, dishes, glassware and more. Bedroom with fresh linens, (queen size bed), clean bathroom, fast Wi-Fi 300 , AC/heat, and free parking. Close to Stony Brook Univ 13 min, Port Jefferson Hospital 15 min, and Suffolk College 5 min

Stylish 2BR House Near Stony Brook University

Experience the ideal blend of style and convenience in this newly renovated 2-bedroom home just steps from Stony Brook University. Enjoy spacious upstairs bedrooms with charming dormers, dedicated workspaces, and a modern bath perfect for quiet study or restful nights. Downstairs, relax in the elegant living room or cook in the stunning chef’s kitchen with a premium gas stove. Walk to the SBU bus stop, stores, great dining, and the popular movie theater. Your perfect Stony Brook rental awaits!

*NEW LUX Northshore River KING, privacy deck/yard

Welcome to the perfect private space to unwind and relax. This completely remodeled King Suite comes with all the conveniences you'll need for a great stay - plus some little touches that we hope make you feel special. The Northshore Corner Oasis, is a fine retreat where you can recharge your batteries and plan your exciting Long Island adventures. 1 block from the beautiful Riverfront, enjoy a short walk to the pizzeria or the bagel shop, or both! Plus, your well-behaved pet is welcome.

Tranquility Getaway, Private Luxe Suite & Backyard

🌿 Welcome to Tranquility Getaway — a luxurious retreat nestled in the heart of Smithtown. Indulge in our Modern Newly Designed 2-bedroom Private Basement Luxe Suite, located on the left side of the property with a short staircase leading to your exclusive entrance on the lower level. Unwind in your private outdoor haven, featuring refined seating for four, a stone-top fire pit, and a solar-lit umbrella. THIS IS NOT THE ENTIRE HOUSE‼️ PLEASE REVIEW 📸 PHOTOS & HOUSE RULES BEFORE BOOKING‼️

Cozy studio w/ private entrance

Perfect for solo travelers or couples.This new, cozy studio is part of a larger home but fully self-contained w/ its own entrance. Inside, you’ll find: - A comfy living area with a pull-out twin bed and seating - A kitchen with essentials for light cooking - A private bathroom with shower, towels, and toiletries - High-speed Wi-Fi and a flat-screen TV Though attached to our home, your space is private. Located in a quiet neighborhood, close to attractions, restaurants, and transportation.

The Harbor House: Beachfront Home 1 hour from NYC

FEATURED #1 on Refinery29's "11 Best Beach Houses Near NYC" Welcome to Long Island’s iconic Gold Coast! Wake up to sweeping waterfront views and, if you’re lucky, catch a glimpse of our local bald eagle family soaring overhead! Explore nearby gems like the Vanderbilt Mansion & Planetarium, Caumsett State Historic Park Preserve, Del Vino Vineyards, and the lively Paramount Theatre. Stroll through Downtown Huntington or Northport Village for boutique shopping, great restaurants.

Cottage in the heart of Stony Brook Village

Stay in a fully renovated 100-year-old cottage that blends historic charm with modern comfort. Your private upstairs suite has its own entrance, perfect for couples, families, or small groups. Walk just ¼ mile to Stony Brook Village shops, restaurants, the fishing pier & beach, or watch the wildlife from your screened-in porch. Only an 8-minute drive to Stony Brook University & Hospital. Experience the perfect mix of village charm, modern amenities, and natural beauty.

Studio in Stony Brook

We have contactless check-in procedure & fully private entrance. Please contact with any questions! Large clean studio space that is totally private from the main residence. Private bathroom with toiletries included. Close to beaches, shopping, and SUNY hospital and campus by car or bus. Pull-out loveseat with twin size mattress available for an extra charge. (Book for “3 Guests” for this regardless of occupancy so we know to prepare the bed.)

The Rosevale Studio Suite

Located just about 10 minutes from the Long Island Rail Road and Long Island Mac Arthur Airport is The Rosevale Studio Suite which combines modern finishes with a cozy, warm charm. Enjoy a lovely lunch in your private patio where the sun hits so perfectly or have a night out at one of the many surrounding restaurants! With shops, beaches and more all located under 5 miles away, our suite is just perfect for your little get away!

Charming “hotel inspired” Retreat

Relax and recharge at this peaceful, centrally located retreat. Your private room features a cozy QUEEN size bed, desk and chair for work or study, TV for entertainment, and a coffee station with microwave and mini fridge for quick bites. Enjoy the privacy of your own bathroom and entrance, with easy on-street parking right in front of the house.

Relaxing Stay: Walk to SBU & Hospital

When you stay in our guest suite, you will have your own Private suite with own entrance, kitchenette, bedroom, bathroom, livingroom. Within walking distance Stony Brook University, train station, village center and Hospital. NON-SMOKING! Please contact the owner before booking. I'm happy to answer any questions you may have.