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Holiday houses in Portland

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Top-rated holiday rentals in Portland

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

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Guest favourite
Cottage in South Frontenac
4.96 out of 5 average rating, 55 reviews

Waterfront A-Frame Getaway on Thirty Island Lake

Welcome to the proudly Canadian enchanting A-Frame on Thirty! Your journey begins along a scenic country road, guiding you through a canopy of trees, where sunlight dances through the leaves, leading you to this charming A-Frame. Experience quiet mornings on the lake as you savor your coffee on the picturesque dock, fishing by the dock or embark on a paddling adventure to explore the pristine waters of Thirty Island Lake. This cozy waterfront retreat promises an unforgettable vacation experience

Top Guest favourite
Cottage in Perth
4.96 out of 5 average rating, 67 reviews

Gorgeous Island View Cottage near Perth Ontario

The perfect year-round getaway for friends & family, a romantic weekend, or simple peace & quiet. If your dates aren’t showing available send us a message, we might be able to make your dates work! This family friendly cottage has 3 bedrooms for up to 4 adults and 2 kids. Private, clean waterfront with a shallow entrance to the lake. Great swimming, awesome views! Located in a beautiful treed setting, large deck, heat/AC, wood stove, canoe, peddle boat, SUP, kayak, BBQ, TV. Pets upon approval.

Top Guest favourite
Home in Portland
5 out of 5 average rating, 16 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, 191 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, 222 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. DO NOT BRING BOTTLED WATER. To swim you must paddle out to a raft. There is a small sandy beach with a wading area for the little children.

Top Guest favourite
Cabin in Lanark
5 out of 5 average rating, 127 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 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, 104 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.

Guest favourite
A rustic log cabin is set among greenery, featuring a sloped roof with metal panels and a welcoming front porch. Large windows provide natural light, while a gravel pathway leads to the entrance. Surrounding grass and dandelions complete the peaceful rural setting.
Cabin in Merrickville-Wolford
4.95 out of 5 average rating, 275 reviews

Cottontail Cabin with Hot Tub and wood fired Sauna

Cottontail Cabin, nestled on 22 acres of serene woods! This is the perfect retreat for those seeking a relaxing and rejuvenating getaway in the heart of nature. The cabin is fully equipped with all the amenities you need to make your stay comfortable and enjoyable. With 2 bedrooms and a pull out couch, the cabin can accommodate up to 6 guests. The cabin features infloor heating and a woodstove to keep you warm and cozy. We have a full-size hot tub and a wood fired sauna!

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.

Top Guest favourite
Tiny home in Perth
4.93 out of 5 average rating, 348 reviews

Off-grid A-frame cabin, come relax in the forest!

Welcome to “The Hemlock” cabin One of two unique cabins on the property. A unique stay situated minutes from historic Perth, Ontario. The Hemlock sits on 160+ acres of private, natural forest. Enjoy 3 season lake access for kayaking & canoe. Year round trails for hiking, snow shoeing, exploring etc. Beautiful scenery and wildlife in a peaceful, private setting, relax and unwind by the fire! We look forward to having you!

Guest favourite
A wooden deck features two blue chairs and a small table with colorful glasses overlooking a calm lake. Lush green trees line the shore, reflecting softly on the water's surface under a serene sky, creating a peaceful outdoor space.
Cottage in Perth
5 out of 5 average rating, 11 reviews

Bass Bay Cottage

Welcome to Bass Bay Cottage, a peaceful, pet-friendly getaway on Big Rideau Lake. This cozy 2-bedroom, 1-bath cottage with a bonus bunkie sits just steps from the water. A screened-in room offers bug-free evenings for relaxing, games, or reading. Enjoy calm mornings, sunny afternoons on the lake, and quiet evenings. Perfect for families or couples looking to unwind. A serene retreat in a quiet bay.

Popular amenities for Portland holiday rentals

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  5. Portland