Vacation rentals in Portland

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Top-rated vacation rentals in Portland

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Top guest favorite

The custom-built chalet is surrounded by lush greenery, with a spacious wrap-around deck featuring outdoor seating and an umbrella. Large windows provide ample light, offering views into the natural landscape. The elevated structure is complemented by a gentle slope down to the surrounding wilderness.

Cottage in Westport

4.98 out of 5 average rating, 153 reviews

Longview: Hilltop Chalet, Stunning Forest Views

Enter Longview and discover endless forest views and an oasis on 88 private acres of wilderness parkland. A custom built chalet complete with all the amenities was designed with care and attention: Scandinavian box bed, rolltop cast iron tub, library loft, fireplace and a huge deck perched over the forest make Longview a truly unique experience and getaway. Ski, snowshoe, hike or spend time with the horses and never leave the property. Longview invites you to unwind and regenerate. Naturally.

Top guest favorite

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, 148 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 favorite

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, 144 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

Guest favorite

An open concept cottage is nestled within lush greenery, showcasing surrounding trees and a well-kept lawn. The structure features a front porch with outdoor seating. A gravel pathway leads up to the cottage, enhancing the sense of privacy on the spacious property.

Place to stay in Lyndhurst

4.94 out of 5 average rating, 71 reviews

Open concept cottage with water access.

Open concept cottage provides a cozy getaway for couples or small groups. There is a boat ramp available on the property that is on the Morton Creek. The waterfront is not great for swimming due to the weeds but there are swimming spots within 10 minutes or take the kayaks and canoes up to the bridge for a swim. 2 acres for lots of privacy and spots for tents. Full kitchen, washing machine, and a full bathroom with a stand up shower. $175/night or $1000/week. The cottage is fully furnished.

Guest favorite

An inviting outdoor fire pit area is surrounded by four Adirondack chairs, with a stone circular seating arrangement at its center. The guesthouse's wooden exterior is visible in the background, framed by lush greenery and a lawn, offering a peaceful and open atmosphere.

Guesthouse in Mallorytown

4.91 out of 5 average rating, 140 reviews

Adorable country guesthouse on Graham Lake

Enjoy the countryside on 15 acres of woods backing on to Graham Lake. Tucked away from the road, our guesthouse is family and pet friendly. The bathroom is newly renovated. Outdoors it boasts a lovely campfire area, a patio table and a large grass yard. Enjoy our gardens in the summer and our laying hens year-round. Take a 5 min stroll down a wooded path to the lakefront where you will find another campfire pit, a dock, a canoe and SUP to use and plenty of space for activities year-round.

Guest favorite

A charming A-frame cottage is set among lush greenery, featuring a wooden front deck equipped with seating. The exterior displays blue siding and light-colored accents, framed by tall trees. Stacked logs provide a decorative element along the foundation. A clear blue sky is visible above.

Cabin in Leeds and the Thousand Islands

4.9 out of 5 average rating, 118 reviews

A-frame Cottage Lakeside, Charleston lake

Welcome to Minnow Cottage, the perfect place to enjoy the lake and nature, spend quality time with loved ones, and relax and recharge! Imagine peaceful mornings on the deck with coffee serenaded by the lake's loons. Swim in one of the clearest lakes in Ontario. Explore the lake on our kayaks, paddleboards and canoe. Bring your fishing gear for some excellent fishing. Savour cozy evenings around the firepit, creating lasting memories under starlit skies. Your lakeside getaway awaits!

Top guest favorite

A modern tiny home is set against a backdrop of lush greenery under a clear blue sky. The exterior features a blend of dark metal and large glass windows, with a welcoming porch and steps leading to the entrance. Comfortable seating is arranged outside.

Tiny home in Lanark

4.98 out of 5 average rating, 149 reviews

Highland House

Step into rural life at Highland House, a charming tiny home perched high on 5 acres in the Lanark Highlands. Perfect for guests looking to unwind in nature, starry skies by the fire, & those incredible sunsets. During the summer months enjoy the farm-fresh experience with hand picked vegetables from the garden and eggs straight from the coop. Home to a friendly pig, chickens, & three fluffy sheep. Experience tiny living in a big way for time with family & friends or a romantic getaway!

Guest favorite

A screened-in porch features a cozy seating arrangement with soft gray cushions on wicker chairs. A round glass table is positioned nearby, and ambient lighting is strung along the wooden beams. The view beyond overlooks green fields and trees, inviting relaxation in nature.

Cabin in Lanark

4.92 out of 5 average rating, 190 reviews

The Owl's Nest Cabin, a peaceful retreat

Welcome to The Owl's Nest, a woody pine cabin overlooking beautiful fields and forests. This completely private cabin offers a cozy, clean, open concept design with large bright windows designed to let the natural beauty of the land inside. Spend days unwinding at the cabin, walking our nature trail, or explore nearby attractions. Hike to the lookout at Blueberry Mountain, or visit local boutique shops, restaurants & beaches around historic Perth. Come Be in nature, explore & relax!

Guest favorite

The interior space features warm wood paneling and an open layout. Two comfortable recliners are positioned on the floor, facing a wood stove. A dining area is visible in the background, with a wooden table and chairs. Bright natural light enters through large windows.

Home in Perth

5 out of 5 average rating, 6 reviews

Romantic and Cozy Winter Waterfront Wonderland

Relax with your special person, a few good friends or your family at this peaceful place to stay. You will love how quiet and serene the lake is. Only 20 minutes to Perth or Westport, 5 minutes to a new hiking trail and 15 minites to Foley Mountain conservation to name a few special places to enjoy nature. This cottage is on a private lake with no public access and is an absolute slice of heaven. Enjoy walks on the quiet road after a fresh snow fall or have a fire lakeside.

Top guest favorite

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, 379 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 favorite

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 favorite

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.