Vacation rentals in Long Island

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Top-rated vacation rentals in Long Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favourite
A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.
Treehouse in Sanford
4.91 out of 5 average rating, 585 reviews

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Top guest favourite
A wooden deck leads to the entrance of the yurt, featuring two green Adirondack chairs flanking the doors. The surroundings are wooded, with a carpet of forest floor visible and trees providing a natural backdrop.
Yurt in Chebeague Island
4.98 out of 5 average rating, 176 reviews

Yurt on Chebeague Island

Imagine staying in a yurt in the woods of Chebeague Island, nestled in a private clearing in the woods. Explore island beaches and hidden trails. This yurt is “glampy” inside with leather chairs and a substantial log bed. The yurt has a rusticator kitchen with all of the basics for cooking: fridge, stovetop, sink, water, firepit & firewood. Outdoor shower. WiFi . Cozy heater for cool spring nights. Ferry options on Casco Bay Lines or CTC Ferry. Host provides transport to/from ferry to the yurt.

Top guest favourite
The image captures an aerial view of a serene landscape with lush green trees surrounding calm waters. The shoreline curves gently, leading to a private dock that extends into the water. A soft sunset glow reflects off the surface, creating a peaceful ambiance.
Home in Georgetown
4.99 out of 5 average rating, 115 reviews

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Top guest favourite
A serene waterfront scene features a small boat gliding across calm waters, reflecting the surrounding buildings. A cluster of white cottages stands on pilings, with a dock visible, under a soft pastel sky as day transitions to evening.
Cottage in Brunswick
5 out of 5 average rating, 207 reviews

Lobstermen's ocean-front cottage

Be our guests & experience the life & beauty of Midcoast Maine. Relax & enjoy the views, warm up in the sauna or go for a refreshing dip. The cottage is part of an over 100 year old working lobstering, and now oyster farming property we call, Gurnet Village. Located right on historic Route 24, we are conveniently situated between Brunswick & the islands of Harpswell. All rooms have ocean views. The tidal beach & the floating dock (May-Dec) is ideal for seasonal fishing, lounging & swimming.

Top guest favourite
A spacious living area features a custom birch couch, accompanied by a wooden side table. Natural light enters through a large window, illuminating the light-toned wood flooring. A staircase with a wooden handrail leads to a loft area above.
Cabin in Georgetown
4.99 out of 5 average rating, 208 reviews

Sauna+Near Beach+Pond+Outdoor Shower+Fire Pit

Relax at your own private forest retreat! * Private Cedar Glass Sauna * Minutes Reid State Park Beach & 5 Island🦞 * Private Outdoor Shower * Private Fire Pit w/S'mores * 100% Cotton sheets/towels * Rain Shower & Heated Bathroom Floor * AC/Heat * SmartTV & Record Player w/Vinyl * Fast Broadband Wifi *Pine Cabin is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart and separated by a privacy screen and natural landscaping.

Guest favourite
A glamping Geodome stands elevated against a twilight sky, illuminated by warm lights. A small fire burns in a metal pit near a seated figure. Surrounding trees add greenery to the serene outdoor setting, creating a calming atmosphere.
Dome in Buckfield
4.84 out of 5 average rating, 256 reviews

StreamSide Getaway- HOT TUB / AC/ Wi-Fi

The Streamside Getaway offers a luxurious glamping experience in a new solar and wind-powered Geodome. Equipped with custom furniture, new hot tub,luxury appliances, free high speed wifi, AC/Heat Unit and modern bathroom and kitchen facilities, guests can enjoy a homely and comfortable stay in nature. A glamping site built in 2022 offers a contactless check-in process with a custom key code. Additionally, we have added archery, axe throwing, and kayaks to enhance your outdoor activity!

Guest favourite
A wooden dock extends toward calm water, with a gentle sloping pathway leading down from the boathouse. The clear water reveals stones at the bottom, while green trees frame the picturesque lakeside view.
Guesthouse in New Gloucester
4.89 out of 5 average rating, 161 reviews

On the water Boathouse!

In the water! Two story boathouse. Originally built in 1939 and parked boats in until 1972. Converted to living space in the early eighties. The upstairs consist of a bedroom walk in closet and a balcony. The downstairs is a living room, kitchen and bathroom. Walk out the door to the patio , dock , and beach! You won't find anything closer to the water! The balcony is the perfect place to watch the sunset, thunderstorms, or sip your morning coffee. Watch the fish out the window!

Guest favourite
The cabin exterior is showcased with large glass walls, allowing natural light to fill the interior. A wooden deck is lined with outdoor lights, leading to a hot tub. Surrounded by trees, the peaceful setting is visible, creating a serene outdoor atmosphere.
Home in Naples
4.98 out of 5 average rating, 181 reviews

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

Top guest favourite
The exterior of the A-frame cabin is showcased, featuring a unique wooden facade and metal roof. Sunlight streams through tall triangular windows, illuminating the surrounding wooded area. A gravel path leads to the entryway, enhancing the cabin's connection to nature.
Cabin in Freeport
5 out of 5 average rating, 120 reviews

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Top guest favourite
A modern cabin structure is surrounded by trees, featuring large glass walls that reflect the evening sky. Warm lights illuminate the deck, highlighting the inviting outdoor space with comfortable seating. A cozy ambiance is created by the gentle glow against the natural surroundings.
Home in South Berwick
5 out of 5 average rating, 133 reviews

Romantic Mirror cabin in the woods

Stay at Hidden Pines Cabins. The Mirror cabin is Maines only 3 sided floor to ceiling mirrored glass cabin. Unwind in the hot tub while looking up at the sky full of stars. Take a sauna while surrounded by nature all around. Located in the majestic forest of mount Agamenticus, the extensive trail system is off of our road. Short drive to the Ogunquit/York beaches, Outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

Top guest favourite
A spacious house with large glass windows is featured, set against a colorful sunset sky. A wide deck extends around the home, with black outdoor furniture positioned for views. The structure is framed by trees and a grassy area, providing a serene atmosphere.
Home in Long Island
4.99 out of 5 average rating, 73 reviews

Whole house on a great island in Casco Bay!

Nona's View is a beautiful spot located on Long Island, Maine in Casco Bay. Long Island is only a 45 minute ferry ride from Portland and this quiet island is great for anyone looking to get away from the stress of the mainland. You will see breathtaking sunsets and will have access to the best beaches in the bay! The house also comes with a golf cart to use during your stay and will be left at the dock for you.

Guest favourite
A scenic view of the ocean framed by green trees and a grassy area. A distant lighthouse is visible on the horizon, while the sky is partly cloudy, creating a peaceful atmosphere. The landscape includes several large rocks scattered across the lawn.
Home in Peaks Island
4.9 out of 5 average rating, 117 reviews

Stunning Ocean Views From This Peaks Island Home

Completely remodeled classic Peaks Island home with stunning Atlantic Ocean white water views. Welcome to the newly renovated Valhalla on Peaks. This classic home underwent a complete renovation for your family's enjoyment. From the minute you step onto the property, your senses will be overwhelmed by the views, ocean breeze, salty smell, and the property's nostalgic feel.

Popular amenities for Long Island vacation rentals

Frequently Asked Questions

  • Where should I stay in Long Island?

    Make yourself at home in Long Island by choosing from our most frequently booked neighborhoods. We have over 1,040 vacation rentals in Peaks Island, over 90 vacation rentals in Cliff Island, and over 1,040 vacation rentals in Saint George.

  • Are there pet-friendly vacation rentals in Long Island?

    Four-legged friends are welcome in Long Island. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Long Island?

    Yes! Work meets play with ease at over 20 vacation rentals in Long Island featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly cottage rentals in Long Island?

    Long Island has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Long Island?

    Experience the best of Long Island with our house rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Long Island have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Long Island. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Long Island have a bbq area?

    Absolutely! We offer over 30 house rentals with a bbq area in Long Island. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Long Island?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with a bbq area, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Long Island

  • Total vacation rentals

    Explore 70 vacation rentals in Long Island

  • Nightly prices starting at

    Long Island vacation rentals start at $151 CAD per night before taxes and fees

  • Verified guest reviews

    Over 2,170 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    60 of Long Island vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Monthly stays, Gym, and BBQ grill across Long Island rentals

  • 4.9 Average rating

    Long Island stays are highly rated by guests—averaging 4.9 out of 5!

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