
Holiday houses in Head of the Harbor
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Top-rated holiday rentals in Head of the Harbor
Guests agree: these stays are highly rated for location, cleanliness and more.

Large and Beautiful Guest Suite
Large beautiful, bright guest suite in a private home. Separate driveway and private entrance. Cathedral ceiling, open floor plan, queen bed, full sofa bed, kitchenette with mini refrigerator, microwave/convection oven combo, Keurig coffee maker, TV with fire stick, gas fireplace (Nov.1 - April 1). Full bathroom with walk-in shower, towels. Washer/dryer. Beautiful covered back porch. Close to shopping, 2 miles from beach, 1 mile from SUNY Stony Brook, and LIRR. 5 miles from Port Jefferson ferry.

All Private Bright Spacious Close to All
DISINFECTED AND CLEANED BEFORE YOU ARRIVE! Spacious ground level PRIVATE apt with lots of natural light. Full kitchen/new stove/fridge/Keurig.Bedrm- queen sz bed, living rm -full sz sofa sleeper. Also available is queen air mattress w/ topper. Washer/Dryer. Minutes away to the Port Jeff Village shops&restaurants/Ferry/LIRR, hospitals, & Stony Brook. Small beaches 10-15min drive, large beaches,Shop Outlets & Wineries 25 -60 minute. PLEASE NOTE: Extra $2 Daily Fee for charging electric car.

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.

Cottage in the heart of Stony Brook Village
Totally renovated 100 year old charming but modern cottage steps from the Three Village Inn, Country House Restaurant, Stony Brook Village, Jazz Club, Sand St. Beach, Avalon Park, Carriage museum and the Long Island Music & Entertainment Hall of Fame. You will have the private upper floor of the cottage with a private entrance. There is a spacious porch and front yard with lounge chairs where you can watch the deer, chipmunks, birds, & rabbits. Short ride to Stony Brook University.

Private Cabin in Multi Acre Park
I have a professional cleaning company come between all guests. The property is the only house on the street abutting several acres of wooded park land. Get the feeling of nature/privacy similar to being up state NY yet centrally located to Sunken Meadow Parkway, Northern State, LIE. Also near food stores and other essentials. 400 MBPS Internet connection for those who need a reliable internet connection for work! Living room has a pull out queen couch if a 3rd bed is needed.

Charming Rustic 1BR with parking
Peaceful cozy 1 bedroom apartment with your own private entrance plus parking. In the best part of Stony Brook surrounded by nature. 5 min drive to beautiful local beach & 10 min walk to SBU. Close to restaurants & shops. Super comfortable king sized bed, 50" smart TV with Netflix, WiFi, amazing kitchen & bathroom. You are going to love staying here;) Coffee and green tea included. No: pets, smoking, food in bed, candles. No parties or checking in after 11pm.

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.)

Private charming Studio Cottage in Nesconset
Escape to this cozy studio cottage, perfect for couples or solo travelers. Enjoy a comfortable full-sized bed, a well-equipped kitchenette, and a welcoming seating area. Located in a peaceful neighborhood, you're just minutes from local parks, shops, and eateries. P.S. Cleanliness is my top priority to make every guest happy all towels and sheets are sanitized and washed every guest checks in before they're arrival.

Quaint Cottage on Long Island's South Shore.
The Cottage is a lovely space enclosed in hedges for privacy on a one acre property. I do have 3 dogs, they are kept in a separate gated area on the property. The cottage is located 3 miles from downtown Patchogue which is enjoying a renaissance. There are many restaurants and cultural activities as well as ferry access to Fire Island (Davis Park) in the warmer weather. We are also the "Gateway" to The Hamptons.

Charming “hotel inspired” Retreat
Relax and recharge at this peaceful, centrally located retreat. Your private room features a cozy full-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.

Private New Apartment
Open concept living. Cathedral ceilings. 1 Bedroom, Full Bath. Private parking. Patio. 5 minutes from train, 15 minutes to MacArthur Airport. Close to Stony Brook, South shore ocean beaches, and the north shore of Long Island. Perfect if you are planning on heading out east to the wineries!

Eco-friendly Private Apartment
We have created another quaint space where you can kick back and relax in this calm, stylish space. This one bedroom apartment has its own entrance, kitchen, bathroom, queen size bed, work area and it’s self check-in. All the amenities of a Super host.
Popular amenities for Head of the Harbor holiday rentals
Stay near Head of the Harbor's top sights
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Home sweet home

Cozy Cottage with all the conveniences.

“A Room for Professionals”

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- Times Square
- Rockefeller Center
- Madison Square Garden
- Bryant Park
- New York Public Library - Bloomingdale Library
- Grand Central Terminal
- Columbia University
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