Vacation rentals in Middle Island

4.88 out of 5 average rating, 139 reviews

Apartment in Medford

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!

4.92 out of 5 average rating, 203 reviews

Apartment in Coram

Private Apartment- close to shops, Pt. Jeff., SBU

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

4.88 out of 5 average rating, 218 reviews

Apartment in Patchogue

Private 1br Apartment on Long Island

Bright & clean 1br apartment with private entrance on a quiet street. Refrigerator, microwave, keurig incl 2 miles to downtown restaurants, bars, breweries, shopping 10 miles to winery & vineyards 3 miles to beaches 3 miles to Fire Island Ferry 30miles to NYC 3 miles to Baseball Heaven 10 miles to Stonybrook University & hospital 1 mile to public horse farm & stable 3 miles to St Joseph's College .5 mile to Long Island Community Hospital 1 mile to hiking 45min to JFK 10min to McArthur airport

4.89 out of 5 average rating, 493 reviews

Cabin in Rocky Point

Great little place just for a couple

The outdoor courtyard is especially nice and private ,with a fire pit, grill and comfortable chairs. It is a rustic location easy walking distance to North Shore Beach. If you want an ocean beach you can drive straight south for 20 minutes and reach Smiths Point State Park right on the ocean. The North Fork with its vineyards is a short drive and the Hamptons also only 30 minutes to West Hampton. You can fish, golf, walk among the wooded area and relax in peace. A pleasure. linen 100% cotton.

4.96 out of 5 average rating, 141 reviews

Apartment in Patchogue

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.

4.74 out of 5 average rating, 163 reviews

Apartment in Ridge

The Silver Pine Cone

Welcome to the hamlet of Ridge. The gateway to Long Islands many treasures. Whether you are venturing out to the North Fork wineries or a scenic drive on the south shore beaches on your way to the Hamptons. A beautiful cozy private (not a shared space) full one bedroom downstairs lower level apartment, living room w/full size sofa sleeper, kitchen/dining room, full bathroom and a completely separate yard with patio furniture exclusively for your use. Everything you need to enjoy your stay.

Guest suite in North Fork

4.9 out of 5 average rating, 271 reviews

Beachy En Suite /Gateway to The North Fork

Adorable,quiet,clean, w private entrance, private bedroom and bathroom,breakfast nook and patio.We are located in a beach front town dubbed“Gateway to the North Fork”.Walking/driving directions to local beaches,15minute walk to our community beach,Wildwood StPk(.6mi away).Niks deli nearby.Minutes by car to wineries,breweries,farm stands,EastWind,TangerOutlets15min away,35min to Hamptons,Greenport!Hosts live in adjoining house.NoTV but Wifi is good so bring your device for entertainment.

4.99 out of 5 average rating, 104 reviews

Place to stay in Coram

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.

Apartment in Farmingville

4.88 out of 5 average rating, 105 reviews

Studio Apt W/Private Entrance & Patio

Enjoy your stay in this private space offers a bedroom with a Queen size bed . Living room includes a smart TV 43" with twin sofa bed and desk for at-home work, kitchen where to find enough crockery for four people, microwave, refrigerator,coffee maker, Free parking on premises. Convenient location with many necessities nearby (gas station/restaurants). We are located 2 mins from I-495 and 14 mins from Macarthur airport. Keep it simple at this peaceful and centrally-located place.

Apartment in Port Jefferson Station

4.9 out of 5 average rating, 116 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.

Guest suite in Stony Brook

4.8 out of 5 average rating, 640 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.)

4.94 out of 5 average rating, 239 reviews

Cottage in Patchogue

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.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Middle Island vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Middle Island

Guesthouse in Miller Place

4.76 out of 5 average rating, 58 reviews

Private guesthouse

LoriRating, 5 stars1 week ago

This place is very peaceful, in a great area with lots of restaurants and shopping nearby. The guest house is extremely clean and there is no clutter. I really enjoyed my stay here and highly recommend this Airbnb if you ever want to get away to someplace peaceful but close enough where you can find things to do.

Apartment in Port Jefferson Station

4.96 out of 5 average rating, 186 reviews

All Private Bright Spacious Close to All

MichaelRating, 5 stars2 weeks ago

I really enjoyed myself on this brief stay and would gladly stay again the next time I’m on Long Island. Everything was positive, from my communication with Edward, to their flexibility when I overslept, to the comfort of the bed. Highly recommended if you’re on Long Island and don’t feel like staying at a hotel.

Apartment in Middle Island

4.96 out of 5 average rating, 67 reviews

Modern Farmhouse Decor With Washer/Dryer

MariRating, 5 stars1 week ago

This is a lovely, bright and spotless apartment with a private entrance. It is immediately apparent the owner has made an effort to not only take care of the basic needs of the client but has also provided thoughtful amenities for their comfort as well. You will feel very comfortable. Communication was timely and all information was provided for entry. I highly recommend it.

Guest suite in Miller Place

4.9 out of 5 average rating, 105 reviews

The Dogwood Inn - An eclectic north shore retreat

JaniceRating, 5 stars4 weeks ago

Great week long visit. Lovely, quiet neighborhood- great for walks. One bedroom unit is clean, roomy, well supplied and with excellent bed. Unit is attached to one end of house but is private with very little noise between the two. Briefly used heater and AC and both worked well. Hosts responsive, friendly and helpful.

4.86 out of 5 average rating, 64 reviews

Cottage in Yaphank

Beautiful Waterfront Cottage

GlennRating, 5 stars2 weeks ago

A beautiful house that felt very spacious for its size. It was very stylish and super comfortable. The backyard was huge with a little bridge that went over the pond, and had daily visits from a rabbit, groundhog and turtle. This house is a great choice if you are visiting the area, with the Expressway a minute away, a Walmart at the next exit going east, and a deli, pizza place and gas station at the corners of your street. Looking forward to staying again

4.9 out of 5 average rating, 79 reviews

Guest suite in Shirley

A&D Airbnb.

CandiceRating, 5 stars1 month ago

Was a cute little basement area. Would book again.

4.98 out of 5 average rating, 50 reviews

Apartment in Shirley

Welcome to Bill & Debbies AirBnb

Kristen BethRating, 5 stars2 weeks ago

The apartment was fantastic! Great location, everything you need for a home away from home. This was perfect for my little family. And the VALUE?! Everywhere in this area is SO EXPENSIVE, so to find Bill's place was an absolute miracle! Highly recommend for your Long Island stay!