Holiday rentals in Portland

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Top-rated holiday rentals in Portland

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Top guest favourite
A sunlit porch features natural wood paneling, creating a warm and inviting space. A small wooden table and chairs are positioned near the window, with soft cushions placed on the seating. Decorative elements, including a figurine, enhance the calm atmosphere of the area.
Cabin in Belleville
4.89 out of 5 average rating, 141 reviews

ZenDen Cabin By The Pond

This unique little eco friendly hobby farm has a vibe all its own. Close to many amenities yet secluded in middle of it all. Wild bird watching, fishing in the pond, long walks in the field to catch the sunset. Enjoy a bonfire or just chill with the view. You will be transported to a peaceful place. Bay of Quinte, Sandbanks, Scenic Caves, Wineries all for you to explore. 8 minutes drive to Shannonville motor sports park Fresh eggs from my hens when they're available Geodesic Dome Greenhouse.

Top guest favourite
A modern living space is highlighted by a high ceiling with exposed beams. The room features a gray sofa, two vibrant yellow chairs, and a minimalist kitchen with sleek appliances. Large windows provide abundant natural light and stunning views of the surrounding landscape.
Cottage in Elgin
5 out of 5 average rating, 156 reviews

Gecieve Opinicon - A Modern Water's Edge Retreat

Escape to your own private sanctuary on beautiful Opinicon Lake. A refreshing and unique gem, this retreat has been meticulously crafted to encourage comfort & relaxation without any fuss – no roughing it here! Whether you choose to unplug & enjoy the serenity of lake life or stay connected online & power through work, you're covered. A few feet from the water's edge, panoramic views are spectacular. *NEWLY RENOVATED *PRIVATE *FAST WiFi *A/C *BOAT LAUNCH *HOT TUB *NO PARTIES * QUIET RETREAT

Top guest favourite
A master bedroom features a queen-size bed with a textured white coverlet. Large windows and sliding glass doors allow for natural light and offer views of the waterfront. A small table is positioned near the window for additional functionality.
Cottage in Hammond
4.97 out of 5 average rating, 175 reviews

River Ledge Hideaway

New construction home designed specifically with the thought of guests in mind overlooking the Saint Lawrence River. Enjoy a memorable fall or holiday getaway to this waterfront oasis. Highlighting this home is a large master bedroom overlooking numerous islands speckled throughout the expansive water view. Outdoor fire pit and grilling area will be set up for the fall season. Walk down our path to your own private waterfront. Great place for couples, small families or friends getting together

Top guest favourite
The exterior of a two-story cottage is shown, featuring a spacious deck with chairs and a table. Large windows allow natural light to fill the interior spaces. The surrounding area is green with trees providing shade, creating a serene lakeside environment.
Home in Lyndhurst
4.94 out of 5 average rating, 221 reviews

Wonderful Canadian Lake House

Imagine vacationing on a beautiful lake with everything you need to enjoy time on the water – kayaks, canoes, paddle boards, pedal boat and rowboat. . Inside is a fully equipped kitchen, very comfortable beds, central air-conditioning, walk-in shower and soaker tub. We have an entire house R/O system, so all the water from every tap is perfect. We live on a bay with many weeds. To swim you must paddle out to a raft. There is a small sandy beach with a wading area for the little children.

Guest favourite
The cabin is situated on a gently sloping green lawn surrounded by trees. A spacious deck is visible, complemented by outdoor furniture. A landscaped area with stone walls and plants can be seen in the foreground, enhancing the natural setting.
Cottage in Leeds and the Thousand Islands
4.92 out of 5 average rating, 231 reviews

Smugglers Getaway on the St. Lawrence River

Enjoy your privacy in this waterfront cabin in the historic Smugglers Cove on the St. Lawrence River in the heart of the 1000 Islands. You'll have use of the entire cabin with fantastic River views from your own patio. Conveniently located off of the 1000 Islands Parkway, one of the most beautiful scenic drives in North America, guests may enjoy walking, hiking and cycling the paved and scenic 37 km Waterfront Trail. You're welcome to arrive by boat or car; private entrance to your cabin.

Top guest favourite
A serene lakeside view showcases a charming cottage with a large deck and a spacious dock. Two stand-up paddle boards rest on the water beside the dock, while adirondack chairs provide a relaxing seating area with scenic views of the surroundings.
Cottage in Verona
4.91 out of 5 average rating, 103 reviews

Birdhouse cottage right on the lake

Charming, renovated 1940s cottage on Howes Lake - 25 minutes north of the 401. Main cottage has a large deck and open kitchen/dining/living room with two bedrooms. Access to the 3-piece bath through master bedroom. Bunkie (when booking 5+ guests, extra charge) is bright and open with a double bed, couch- no heat. Water is great for swimming, fishing & boating. Three stand up paddle boards are provided seasonally. Only 3km from Verona with LCBO/Beer/ Grocery store etc. No wifi, no pets.

Top guest favourite
A two-story historical house combines brick and modern design elements. Large windows provide natural light, and a landscaped garden features colorful flowers in front. The gravel driveway leads to the entrance, while greenery surrounds the property, creating a rural ambiance.
Farm stay in Perth
4.99 out of 5 average rating, 239 reviews

Motherwell House-entire house-countryside stay

Welcome to the historical Perth area. We hope you will enjoy your stay at our rural setting, close to amenities but surrounded by the sounds of the countryside. Our house has all the comforts of home with beautiful open vistas visible out each window. This property was deeded to the Motherwell family following the War of 1812, staying in their family name 100 years. The interior of the house is fully renovated with some exterior projects ongoing. HST included in our pricing.

Top guest favourite
The exterior of the loft showcases a wooden structure with a rustic design, featuring a steeply pitched roof and two prominent garage doors. Flanking the entrance are tall evergreen trees and well-maintained shrubbery, contributing to a natural, inviting environment.
Loft in Hammond
4.93 out of 5 average rating, 200 reviews

Come to The Lake House Loft for a relaxing visit!

The Lake House Loft is located in Upstate New York on Black Lake, known as “Freshwater Fisherman’s Paradise”. It is the largest St. Lawrence County Lake and is over 20 miles long. Its located near the Canadian Border, close to Ogdensburg and the Thousand Islands. This is a smoke-free, two-bedroom loft, with a full kitchen, and a bathroom. There is a 100-foot waterfront boat dock available, Wi-Fi, A/C, Heat, and is fully furnished. Paddle Boat and canoe also available to use.

Top guest favourite
A charming cottage exterior is framed by lush greenery. A metal roof and blue wooden siding complement the three front windows and central door, while orange daylilies add a pop of color to the surrounding garden. The front porch features steps leading to the entrance.
Cottage in Leeds and the Thousand Islands
4.97 out of 5 average rating, 406 reviews

Lyncreek Cottage

Lyncreek Cottage is open year round. it sits on private property on Lyndhurst river in Lyndhurst, Ontario. Observe various types of waterfowl or enjoy the sound of our meandering river as it flows into Lyndhurst Lake. This is all part of the natural surroundings in your own private cottage. A great place to stay if you are travelling through the area or while enjoying all the area has to offer including excellent fishing, paddling and hiking area trails.

Top guest favourite
The exterior of a cabin is presented, showcasing wooden siding adorned with climbing greenery. Large windows allow natural light to enter, with flower boxes situated beneath them. The structure is framed by trees, creating a harmonious blend with the natural surroundings.
Cabin in Verona
4.97 out of 5 average rating, 120 reviews

Place: Bright and Cozy Woodland Retreat

Custom-built year-round retreat in the Frontenac Arch, nestled in the woods—private, quiet, and steps to the lake for canoeing or SUP adventures. Relax on the deck under the stars or soak in the hot tub after a day of adventure. Enjoy vaulted ceilings, soaring windows, a wood stove, outdoor fire pit, custom kitchen, heated floors, rain shower, clawfoot tub, and a bright open layout. 25 mins to Frontenac Provincial Park and 40 mins to Kingston.

Top guest favourite
An inviting exterior view of the property features a wooden deck adorned with soft lighting. A covered seating area includes a small table and chairs, enhancing the outdoor space. Lush greenery surrounds the home, creating a tranquil setting for relaxation.
Place to stay in Spencerville
5 out of 5 average rating, 110 reviews

Honeybee Haven - Dog Friendly, Free Parking

Escape to a cozy, dog friendly haven, perfect for embracing the magic of the winter season. Nestled in a picturesque landscape, our property offers all the comforts you need for a memorable stay. Whether you’re here for adventure, romance or relaxation, Honeybee Haven is your ultimate winter getaway. Located minutes off of Hwy 401 and the US border crossing, an hour from both Kingston and Ottawa and two hours from Montreal.

Top guest favourite
The exterior of a charming cottage is presented, featuring a shingled facade and distinctive gabled roof. The structure is surrounded by greenery, with a wooden fence in the foreground, displaying a vintage bicycle resting against it. Steps lead up to a deck at the side.
Loft in Lanark
5 out of 5 average rating, 201 reviews

Cozy Waterfront Loft | Hot Tub + Forest Views

Welcome to The Loft at Closs Crossing! A cozy, open concept space where you can relax, unwind and reconnect with nature. Enjoy your morning coffee on the deck, listening to the birds. Spend the afternoon on your private waterfront dock, reading a book or kayak up river and float back down. In the evening, roast marshmallows on the campfire or take a relaxing soak in the hot tub. Your cottage country escape awaits you!

Popular amenities for Portland holiday rentals

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