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Holiday rentals in Portland

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Portland

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

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Top guest favourite
The Swim Spa hot tub is illuminated with soft blue lights, creating a serene atmosphere. It is positioned on a wooden deck with views of the modern lake house. Large bay windows reveal a softly lit interior, enhancing the tranquil evening setting.
Home in Portland
5 out of 5 average rating, 18 reviews

Waterfront Lake House

Take in the breath-taking views of Big Rideau Lake from this beautiful, four-acre lake house. The luxurious property is private, with no direct view of neighbours, and you can watch the sunset from any room or on the dock while enjoying the beautiful shorelines. Unwind and relax while taking in the sounds of nature while sitting in the Swim Spa hot tub or while walking in the woods. This year-round lake house is brand new and the perfect place for friends and families to make special memories.

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
4.96 out of 5 average rating, 202 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
Dome in Westport
5 out of 5 average rating, 19 reviews

The Big Dipper - Geo-Desic Dome

Sleep amid the stars and the deer in the Big Dipper Geo-Desic off-grid dome. A perfect getaway for 2 (or on your own), you’ll sleep comfortably in a queen-size bed with all of the must-have amenities, including an in-unit compost toilet and a woodstove. Cook your meals over the fire or grill and bask in the sunsets from the wood-fired hot tub (seasonal) or cozy in the dome through the panoramic window. Enjoy some modern comforts while getting up close with nature so you can truly unwind.

Top guest favourite
A charming cottage is nestled among the trees, featuring wooden decks and outdoor seating areas. The sunset reflects on the calm lake water, providing a serene view. Lush greenery surrounds the property, enhancing the natural setting.
Cottage in Tichborne
4.94 out of 5 average rating, 120 reviews

3 BR Lakefront Beach Retreat; Hot Tub, Fire Pits!

Relax with the whole family at this cozy lakefront property. Complete with your very own sandy beach, kayaks, hot tub, and multiple outdoor dining and fire pit options, this cottage nestled in the Canadian wilderness is a must-visit! Whether you're coming during the summer to enjoy swimming in the clear water at Bob's Lake or you're searching for a cozy winter escape, look no further. Close to the K&P trail system, hiking, snowmobiling, and water sports, adventure and relaxation await!

Top guest favourite
Cabin in Lanark
5 out of 5 average rating, 132 reviews

Waterfront Cabin | Cozy Treehouse + Hot Tub

Welcome to The Cabin Treehouse at Closs Crossing! Escape to a private waterfront retreat on the beautiful Clyde River. This unique stay pairs a cozy two-bedroom cabin with a dreamy treehouse, set on a quiet peninsula surrounded by water on three sides. Sip your morning coffee under the pergola as birds sing, paddle upriver by kayak, or unwind on the dock. End the day by the campfire or relax under the stars in the hot tub. The perfect blend of comfort, nature and tranquility awaits.

Top guest favourite
An evening view of the cabin's entrance is lit by soft outdoor lighting. A welcoming porch features a wooden railing and decorative elements, while plants surround the steps. The structure has large glass windows, allowing a glimpse of the interior ambiance.
Farm stay in Newburgh
5 out of 5 average rating, 127 reviews

Escape Goat Hideaway at Barking Goat Farms

“Glamping” at its best. Come experience an off grid all season cabin, tucked away in a very private location at Barking Goat Farms, between Toronto and Ottawa. Enjoy your morning coffee on the lovely screened in porch and spend you evenings around the campfire star gazing amid the peaceful surroundings. Many local attractions to visit or just unplug and relax. Perfect for a couples romantic escape or a fun girls getaway. Enjoy a complimentary meet and greet with our goats and donkeys

Superhost
A geodesic dome structure is illuminated at dusk, featuring large windows that provide views of the wooded surroundings. A wooden deck extends from the entryway, leading into a peaceful natural setting.
Dome in North Frontenac
4.77 out of 5 average rating, 88 reviews

The Nest at Bellevue

Escape to our secluded dome in the woods, offering unparalleled lake views. Relax in our cozy retreat with a king-sized bed, fully equipped kitchen, and modern bathroom. Outside, enjoy the cozy hot tub or navigate a staircase to the lake's private seating area and dock. At night, savor the lakeside propane fire pit, watch a movie on the projector from your plush bed, or gaze at the stars through the dome's large porthole. Immerse yourself in nature's tranquility and cosmic beauty.

Top guest favourite
An open living area features a modern kitchen island with bar stools, complemented by a comfortable seating nook. Natural light floods the space through large windows, revealing a peaceful winter landscape. The rustic coffee table and simple decor enhance the cabin's cozy ambiance.
Cabin in South Frontenac
5 out of 5 average rating, 116 reviews

Our Lakeside Getaway

Enjoy the beauty of South Frontenac from the quiet comfort + modern luxury of our lakeside cabin. Located in Eastern Ontario’s cottage country, our cabin is nestled on a small, peaceful lake 15 minutes west of Westport, Ontario. This space is ideal for 1-2 adults. This newly renovated cabin sits on a shared 3-acre property with our family’s lake house. This home-away-from-home has been in our family for 17 years + we’re thrilled to share a piece of our paradise with you.

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, 422 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.

Guest favourite
An aerial view captures a well-maintained pool surrounded by a spacious patio and lounge chairs. Lush greenery and trees frame the inviting landscape, while the heritage home stands gracefully in the background, highlighted by a soft sunset sky.
Home in Portland
5 out of 5 average rating, 32 reviews

The Sheldon Manor & Vineyard

The Sheldon Manor, a slice of Canadian history, is a heritage home built in 1865 with sandstone quarried from the land. The home exudes timeless elegance with its sandstone exterior, wraparound porch and stately sitting rooms. The property boasts modern comforts including a hot tub, heated pool, fire pit and vineyard. Rich in history, the manor offers serenity on its sprawling 4.5 acre lot, beckoning guests to explore its enchanting charm.

Top guest favourite
A charming cottage exterior features large glass sliding doors and a well-maintained deck, adorned with red chairs and vibrant flower beds. Lush green grass surrounds the cottage, which is framed by tall evergreen trees, creating a serene outdoor setting.
Cottage in Portland
4.99 out of 5 average rating, 97 reviews

Beautiful Waterfront Cottage on the Big Rideau

Enjoy your getaway on the prestigious Big Rideau Lake, the largest lake in the Rideau Canal System, a UNESCO designated site. We are located in Portland On. We are walking distance to Len’s Cove Marina. This is very convenient to rent a boat, launch your own in the public boat launch or go for lunch or dinner at their licensed Galley Restaurant. Our cottage has heat and air conditioning. We can communicate in French and English.

Guest favourite
A rustic cabin is positioned on a gentle rise, framed by lush greenery. Reflections of the structure and surrounding trees are visible in the calm water of the private canoe pond. Soft light emanates from the windows, hinting at a cozy interior atmosphere.
Home in Perth
4.89 out of 5 average rating, 27 reviews

Livnlife in nature’s paradise!

If you’re seeking privacy, a romantic escape, or quality time with family and friends, this nature lover’s paradise is for you. Take in unbelievable views overlooking your own private canoe pond and explore a secluded beaver dam hiking trail right on the property. Located just 15 minutes from downtown Heritage Perth, with Murphys Point Provincial Park only minutes away, this is the perfect blend of seclusion and convenience.

Popular amenities for Portland holiday rentals

  1. Airbnb
  2. Canada
  3. Ontario
  4. Leeds and Grenville
  5. Portland