Holiday rentals in Middle Island

Private King Suite in Quiet, Cozy Setting

Separate apartment with private keyless entrance. Cozy one bedroom king suite and sofa with full pull out bed. Full kitchen and dining area. Bathroom with standing shower. Free parking on premise for up to 2 cars. Quiet, family friendly neighborhood. Located in the heart of Long Island. Close to everything! Wineries, Farms, breweries, golf, shopping, great dining. NYC is a only a train ride away! Conveniently located within a mile of groceries and laundromat. High speed WiFi, 55in smart tv

Value · Family · Comfort

Spacious 1Bedroom Apartment By Wineries & Beaches

Relax and unwind in this private, spacious 1-bedroom apartment designed for comfort, convenience, and a peaceful stay. Whether you’re here for a weekend getaway, visiting the North Fork wineries, or need a quiet place to work remotely, this space has everything you need. Enjoy fully private apartment with its own entrance and yard - giving you uninterrupted freedom. Comfortable bedroom, cozy living area & full kitchen Relax in or after a day exploring nearby beaches, wineries, and attractions.

Value · Family · TV

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 · Cleanliness

Charming 2 Bedroom apartment

Enjoy our charming 2 Bedroom apartment that is in a quiet and friendly neighborhood in a cul-de-sac. Private entrance on first floor of our house with 2 Bedrooms, 1 Bathroom, Living room, Dining area, and a Kitchen. Close to: Main highways (Sunrise HWY/Long Island Expressway), Grocery stores, Winery & Vineyards, Davis park ferry, Downtown Patchogue village (Restaurants, bars, breweries, shopping), Beaches, Top Golf, MacArthur airport, Long Island Community Hospital, St Joseph’s College.

Value · Location · Comfort

Long Island Getaway w/ Heated Pool & Lake

Long term bookings available for Summer 2026! Discounts for longer stays! Heated pool open May-Sept We welcome you to our beautiful home full of history, designed with high end comforts, and filled with activities and amenities. Take advantage of everything Long Island has to offer, situated a short drive away from East End LI - close to NYC, Hamptons, NoFo, beaches, wineries, breweries and more! Relax at home in the heated pool, light a bonfire, play games, and many other activities!

Location · Family · Amenities

Family Retreat with Heated Pool, Hot Tub, Sauna.

🛏 6 Bedrooms, 9 beds & 3 Full Baths 🏊‍♂️ Heated Pool & Relaxing Hot Tub 4-person Sauna 🏀 Half Basketball Court & 🏐 Volleyball Area 🏌️‍♂️ Private Golf Putting Green 🔥 Cozy Firepit & Outdoor Lounge Area 🛝 Swing Set & Kid-Friendly Yard 🍽 Fully Stocked Kitchen & Spacious Dining 🌐 High-Speed Wi-Fi & Smart TVs 10 min to Smith Point Beach & Boardwalk 15–20 min to Long Island Wine Country Nearby hiking at Wertheim Wildlife Refuge Short drive to Tanger Outlets & restaurants

Location · Family · Quiet

North Country Cottage

Located near Long Island's beautiful beaches, vineyards, and wedding venues, this cozy cottage in the woods provides a quiet and comfortable place to stay while visiting! A spacious patio extends the living area, adding space to enjoy the outdoors in front of the fire pit or outdoor dining table. This property is located behind the owners' home and uses a shared driveway. While the owner is close by to address any issues during your stay, your space allows for total privacy.

Family · Location · Grill

Private 2 bedroom basement w/ private entrance

Newly renovated, very clean, quiet, private basement apartment setup. Tv in living room and sperate TVs in each room with all streaming services (must use own log in) 1 King size bed 1 Queen size bed Only entire basement available. Reservation must be made by the person or persons staying in the listing. Booking for other people (Third party booking) is not allowed. NO visitors allowed inside listing. NO extra guests (unless it was booked that way) *HMO taxes applied*

Family · Value · Sleep quality

Stunning Guest Suite in Medford

Welcome to our stunning two-bedroom suite on the first floor of our high ranch home. Enjoy a quiet, self-contained retreat where your comfort and privacy come first. The second floor is private and occupied by the host. Our home is close to local shops and transport. You can enter the suite through our calm backyard, creating a calm and welcoming atmosphere. PLEASE CHECK THE PHOTOS and HOUSE RULES BEFORE BOOKING to ensure the space meets your needs. Enjoy your stay!

Location · Value · Check-in

Blue apartment in Long Island, Ny

Welcome to our blue apartment a Peaceful, comfy one bedroom apartment suitable for 4 people. Private bedroom has a Queen size bed with comfy mattress and two small closets to keep your belongs. Living room has two twin comfy beds, tv and desk. Kitchenette is equipped with necessities for a quick meal and coffee maker. You can also enjoy the shared backyard with the fire pit. Keep in mind if you stay past our check out time you will be charge an extra night.

Location · Value · Laundry

Peaceful 3BR Garden Cottage | Long Island Escape

🌿 Escape to a peaceful 3-bedroom retreat in Coram, perfect for relaxing, and exploring Long Island. Enjoy a bright sunroom, cozy living room, fully equipped kitchen, dining area, and private backyard with a charming gazebo. Nestled in a quiet neighborhood, yet just minutes from Stony Brook University and Hospital, Port Jefferson, beaches, parks, shopping, and dining. Perfect for families, healthcare travelers, visiting professionals, and peaceful getaways.

Location · Family · Decor

Medford Seclusive Getaway

A weekend getaway at Medford Seclusive offers a perfect escape for relaxation and recreation. Imagine checking in and settling into your comfortable accommodations. Perhaps a room overlooking a plush garden or the sparkling pool. You’ll spend the weekend enjoying a variety of activities, like playing a game of ping pong or cornhole. Evenings might involve a fire side chat at the outdoor fire pit. You’ll check out feeling relaxed and rejuvenated.

Family · Value · Quiet