Vacation rentals in Head of the Harbor

Cottage in the heart of Stony Brook Village

Stay in a fully renovated 100-year-old cottage that blends historic charm with modern comfort. This is the perfect cottage 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. 2 Queen private bedrooms + full size sofa bed. Sleeps 5

Value · Family · Comfort

Newly done basement apartment Great location

Keep it simple at this peaceful and centrally-located place. A spacious private apartment located at our family home - has a separate entrance and driveway parking.. It is conveniently located off major roadway, which offer a quick access to the LIE, just a 5 minute ride to the Port Jefferson -Bridgeport ferry, and the scenic Port Jefferson Village and the LIRRalso Mather and St. Charles Hospitals 10 minutes to Stony Brook Hospital and University. Close to many restaurants and local beaches.

Value · Location · Kitchen

*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.

Family · Value · Hot tub

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‼️

Family · Location · Nearby

Rivazi Home | Boutique Retreat in Port Jefferson

Welcome to Rivazi Home, a beautifully renovated modern retreat in Port Jefferson. Wake up to sunlight through the trees, enjoy your morning coffee surrounded by nature, and spend your days exploring nearby beaches, the harbor, shops, local restaurants or unwind by the spa. A chef-inspired kitchen features premium appliances and expansive windows that bring the outdoors in. The perfect home base for wedding guests, graduation visitors, families, couples, and peaceful Long Island getaways.

Location · Family · Getting around

Port Jefferson Convenient, Cozy and Chic!

Bright, modern, newly renovated and landscaped space can sleep up to 6! Countless amenities including a kitchen with dishwasher, full size refrigerator. 3 bedrooms, 2 full baths, and common living space. Great for boaters or attending events in Port Jefferson, Stony Brook or anywhere on Long Island. We are a 1 minute drive or 10 minute walk from Port Jefferson Harbor and Ferry Dock. Centrally located on LI for easy access to LI rail road and bus routes.

Family · Location · Getting around

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.)

Value · Location · Comfort

Harborfront Star Walk to Harbor & Village

** Airbnb Fees are now included in the nightly Rate* **Coastal Retreat** Perfectly located just steps from the waterfront, placing you within easy walking distance of the marina, Harborfront Park, boutique shops, cafés, restaurants, and the ferry. Whether you’re here for a relaxing getaway, visiting Stony Brook, or exploring Long Island’s North Shore, this home offers the perfect blend of comfort, style, and location.

Location · Family · Bathroom

White Cottage East Setauket

Nestled in East Setauket, this charming White Cottage offers a cozy retreat surrounded by landscaped grounds. Inside, bright living areas with hardwood floors and large windows fill the home with natural light. The peaceful backyard is perfect for unwinding. Conveniently located near shops, schools, and scenic trails, this cottage offers the ideal escape on Long Island’s North Shore.

Location · Family · Quiet

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.

Family · Location · Condition

Summer Retreat: Heated Pool, Game Room, Playground

POOL CLOSES 1st-2nd WEEK OF OCTOBER 2026: Escape to the ultimate summer retreat! Enjoy a private saltwater heated pool, fire pit, game room, and family-friendly fun in this spacious Long Island oasis. Just minutes from Cedar Beach and perfect for groups, families, or couples. Relax, play, and make unforgettable memories—your perfect getaway starts here!

Location · Family · Indoor spaces

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!

Value · Family · Laundry