Holiday rentals in Head of the Harbor

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Top-rated holiday rentals in Head of the Harbor

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Guest favourite

Flat in Stony Brook

4.93 out of 5 average rating, 41 reviews

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;)

Top guest favourite

Flat in Ronkonkoma

5 out of 5 average rating, 15 reviews

Hotel-Style Studio in Ronkonkoma

Suite 2283 is a hotel-inspired studio apartment in Ronkonkoma. Thoughtfully designed, featuring a private entrance, private fenced-in yard, patio with bistro set, onsite parking, AC, kitchen, Roku TV and free Wi-Fi. This stylish apartment is ideal for traveling medical and business professionals. Just minutes from the airport, hospitals, corporate parks, major roadways, restaurants, parks, the mall, nightlife at the new Station Yards complex at the LIRR hub, and, of course, Lake Ronkonkoma!

Guest favourite

Place to stay in Coram

4.99 out of 5 average rating, 109 reviews

T&T Unique Space

NEW ! Private renovated studio attached to a single family home. Private entrance queen bed w/full bathroom, sofa, 55”smartTV, kitchenette(no stove)free street parking in front of house.This is a drug free, non-smoking, no pets and no party unit. Minutes from Port Jefferson pier, LIRR, Connecticut Ferry, 15 min. to Mac Arthur airport. Shopping in Riverhead at Tanger Outlets a few exits from the LIE. 10min. to John T Mather Hospital & St Charles Hosp. Near Jakes 58 Casino and Top Golf.

Top guest favourite

Place to stay in Saint James

5 out of 5 average rating, 28 reviews

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.

Top guest favourite

Home in Stony Brook

4.99 out of 5 average rating, 133 reviews

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.

Top guest favourite

Tiny home in Centereach

4.96 out of 5 average rating, 114 reviews

The Oasis Tiny House

This Custom Built Modern Tiny House Is Private And Cozy. Our Location In Centereach Long Island, NY Is Just That...In The Center Of Long Island So Whether You Want to Visit The Local Beaches Or Treat Yourself To Some Well Deserved Shopping This Location Has It All, Museums, Shopping Malls, Tanger Outlets, Wine Country, The Hamptons, And New York City Are All Close By. It Is Also Conveniently Located Just A Few Miles From SUNY Stony Brook If You’re Planning To Visit The College

Superhost

Flat in Centereach

4.79 out of 5 average rating, 189 reviews

Spacious one Bedroom Apt with private entrance

Beautiful spacious Apartment w/ private entrance. 1 master bedroom w/Queen bed, dresser, closet & Flat screen T.V. Full kitchen & dining.Gas stove & oven. Living room W/Flat screen T.V, Sofa bed. Renovated bathroom w/shower. Ideal for a weekend get away or work trip. Located minutes from Stonybrook University/Hospital. Convenient to Long Island Airport &Long Island Railroad. If you’re looking for good food & shopping you’ll love it here. Unfortunately we no longer allow pets.

Guest favourite

Flat in Port Jefferson Station

4.91 out of 5 average rating, 128 reviews

The Elite Enclave

Welcome to our newly expanded and renovated Airbnb home! This elegant and modern space has been meticulously designed to provide travelers with a comfortable and unforgettable experience. Outfitted with state-of-the-art amenities and conveniences, every detail of this home has been carefully considered with your comfort in mind. Ideally located just an 8-minute drive from the Bridgeport & Port Jefferson Ferry. We are dedicated to making your stay with us truly exceptional.

Superhost

Flat in Centereach

4.68 out of 5 average rating, 361 reviews

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. Construction onsite currently and guests may experience some noise.

Guest favourite

Guest suite in Stony Brook

4.8 out of 5 average rating, 649 reviews

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.)

Guest favourite

Flat in Huntington Station

4.89 out of 5 average rating, 111 reviews

Clean Cozy Studio with Private Entrance.

Comfortable Safe Studio With Private Keypad Entrance in Huntington Area. Premium CABLE TV and All Amenities described are Included. There is Keurig coffee maker with cream and sugar so you can enjoy it. Cozy studio also has a toaster, microwave, refrigerator, own bathroom and small kitchenette that you can enjoy your own meals. You have a comfy King size Bed.

Top guest favourite

Guest suite in Lake Ronkonkoma

4.99 out of 5 average rating, 277 reviews

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!