Holiday rentals in Head of the Harbor

Cozy Apartment with King Bed - Separate Entrance

Enjoy your stay in this private, clean and comfy environment. Space offers a bedroom with a king size bed and a desk for at-home work. Living room includes a smart TV and a sectional. Unleash your inner chef! Access to kitchen utensils, dinnerware, and pots/pans. Free parking on premises. Convenient location with many necessities nearby (mall/gas station/restaurants). We are located 2 mins from I-495 and 15 mins from Macarthur airport. Great for visiting family in Port Jefferson, Patchogue, etc!

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, laundry access, lots of storage, amazing kitchen & bathroom. You are going to love staying here;) Bring favorite coffee/tea. No: pets, smoking, food in bed, candles. No parties or checking in after 11pm.

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.

1 bedroom w/ private wellness indoor lap pool

Exclusive private use of entire indoor pool and pool room, private driveway, 1 bedroom, 1 private bathroom. 5 minute walk to a picnic beach area. Your space includes a mini fridge, microwave, bar, keurig coffee maker, chaise lounges for chilling in all seasons. The pool is used as a wellness cold plunge in the winter months and lap training pool. It is not heated but the entire pool space is exclusive and private. Private side yard with Adirondack chairs, string lights and fire pit.

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.

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!

Modern style Spacious Getaway

This apartment offers a living room, dining area, bathroom, and a bedroom. The apartment is very spacious so you will never feel cramped and is stylish giving it a unique, creative vibe. The apartment is attached to the side of a house with the owners living on one side. The apartment is partitioned from the main house making it private. There is potential for noise sometimes. There are no hidden fees.

Cozy Riverside Cottage

This is a private cottage on its own lot with its own driveway and yard located in a quiet residential neighborhood. Several grocery stores and restaurants for delivery/pick up in the area. 400 MBPS Internet connection for those who need a reliable internet connection for work/movie streaming! Please note guest maximum is 4. There are no additional guests or visitors allowed.

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 studio with Private entrance

We have created this quaint space with our guest in mind in order to keep it simple at this peaceful and centrally-located place. Studio apartment with your own entrance, kitchen , bathroom, queen size bed and work area. Self check-in. All the amenities of a super host.