Holiday rentals in Winchester Springs

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Top-rated holiday rentals in Winchester Springs

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Guest favourite
The exterior of the house is depicted with warm wooden siding and expansive windows. A spacious upper balcony and lower patio area are visible, featuring outdoor seating. Lush green lawn and well-maintained shrubs surround the home, with trees providing additional greenery in the backdrop.
Home in Iroquois
4.84 out of 5 average rating, 138 reviews

Relax on Butternut Bay

Breathtaking views of the St. Lawrence Seaway from this river side house among mature trees, lawns and perennial gardens. Three bedrooms, one with on-suite bathroom, in total sleeps 8 with two double beds, a queen bed, a double sleeper sofa bed and a set of bunk beds. 2 full kitchens w/gas stoves, family room w/walk-out to patio & BBQ. Living and dining area with walk out deck. The shared beach is good for Swimming, canoeing, fishing in Butternut Bay. Watch cargo ships navigate the river.

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, 183 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
A modern kitchen area features rustic wooden cabinetry and a sleek granite countertop. A stainless-steel refrigerator stands beside a sink, with light fixtures hanging above. The open space leads to a cozy living area in the background, where a spacious bed is visible through an entryway.
Farm stay in Summerstown
4.95 out of 5 average rating, 102 reviews

Unwind in the Countryside at Fraser Creek Farm

Unwind in the countryside of South Glengarry. Our location is close to Ottawa, 124 km SE, and Montreal, 81km West, 20km east of Cornwall and 10km south of Williamstown. Embrace the peace and beauty of the orchard during the spring, summer or fall. Breathe in the refreshing winter air. This is our home property, you may see children exploring with one collie, chickens free ranging and waking to a rooster. Ideal for fishermen who want the St. Lawrence River. We start pizza in Spring ‘24.

Guest favourite
The exterior of the log cabin features a green metal roof and natural wood siding, complemented by snow covering the ground. The front porch is supported by wooden posts, with two chairs placed outside, inviting relaxation in the tranquil wooded surroundings.
Cabin in Merrickville-Wolford
4.95 out of 5 average rating, 271 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
A spacious heritage home is set amidst lush greenery, framed by stately trees. The exterior features a blend of stone and large windows, allowing natural light to illuminate the interior. A well-maintained lawn complements the inviting atmosphere of the property.
Home in Merrickville-Wolford
4.96 out of 5 average rating, 112 reviews

Heritage Stone House & Spa on the Rideau Canal

Experience heritage and relaxation! Stay in this beautifully renovated 1827 stone home on the Rideau Canal, accommodating up to 14 guests. Enjoy kayaking to Merrickville, book farm experiences nearby, or unwind in our new sauna and cold plunge. Watch boats glide by from the deck, soak in the serene setting, and make memories with friends and family. Pets welcome ($25 fee). *NEW - Massage from RMT as well as Manicures & Pedicures - message us for more info

Top guest favourite
Home in Morrisburg
4.9 out of 5 average rating, 264 reviews

StoneCropAcres Winery and Vineyard Guest Home

Our home is located at our StoneCropAcres Winery and Vineyard. Please check the Winery's website stonecropacres for Winery hours of operation. Our Guest Home is a country style, spacious, bright and clean home with wonderful views of the rural surroundings including our vineyard, farm fields, and the apple farm just around the corner. Both the Guest Home and the Winery are wheelchair accessible and there is an electric medical bed available for use.

Top guest favourite
Flat in Winchester
5 out of 5 average rating, 23 reviews

Bright Modern Apartment Backing onto Golf Course

Bright, modern lower-level apartment with stunning golf course views. Perfect for couples or remote workers, this private suite offers peace, luxury, and comfort with large windows, natural light, in-floor heating, AC, advanced air filtration, and pure remineralized water. Features include a modern open layout, dedicated desk, ample parking, and thoughtful design—your ideal retreat to relax, recharge, or work in quiet comfort near Winchester.

Top guest favourite
The exterior of the home features a welcoming porch framed by wooden beams. A white railing surrounds the area, with a small seating arrangement positioned beneath it. The light grey siding complements the blue sky, creating a serene first impression.
Home in Winchester
4.96 out of 5 average rating, 190 reviews

RARE Tiny House 2 BEDS + Free WiFi + 30m to Ottawa

Welcome to The Lofty Nest! Located 30 minutes south of Ottawa (Canada's Capital City) in the intimate village of Winchester. This 2-bed Century home was gutted and lovingly restored, using reclaimed materials, sweat and love. Visiting for work, play or just the experience of living in a tiny house, the Lofty Nest will charm you with its 'Instaworthy' decor and hotel standards. Perfect for 1 or 2 guests; can accommodate up to 4.

Top guest favourite
Place to stay in Spencerville
5 out of 5 average rating, 115 reviews

Honeybee Haven - Dog Friendly, Free Parking

Escape to a cozy, dog friendly haven, perfect for embracing the magic of the spring 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 getaway. Located minutes off of Hwy 401 and the US border crossing, an hour from both Kingston and Ottawa and two hours from Montreal.

Guest favourite
A serene view of the river at sunset, with vibrant colors reflected on the water's surface. Several kayaks in various colors are lined up on the grassy bank, surrounded by lush trees that frame the scene.
Cottage in Chase Mills
4.92 out of 5 average rating, 151 reviews

Lazy River Cottage

This well loved family-friendly river cottage is ready for you. The river is just steps from the house with breath taking views and sunsets to remember. Great fishing from the waterfront and dock. Enjoy a fire in the fire pit near the shore. The water is wonderful for those swimmers in your family. There are paddle boats and kayaks in season. Conveniently located close to St. Lawrence University and Clarkson.

Guest favourite
The exterior of the chalet is showcased, featuring a wooden structure with a green roof. A spacious deck extends from the front, furnished with red chairs. A grassy yard leads to the surrounding trees, and a kayak is visible on the ground nearby.
Cottage in South Stormont
4.82 out of 5 average rating, 227 reviews

4 Season Waterfront Chalet Ault Island Sleeps 12

Unique and cozy 4 season waterfront chalet located on Ault Island, only a few minutes away from Upper Canada Village and Upper Canada Golf Course. The chalet has 3 bedrooms, loft, rec room, living room with wood burning fireplace and kitchen combined with cathedral ceilings and windows overlooking the St. Lawrence River. A must see...!

Guest favourite
A spacious deck surrounded by wooden railings overlooks a calm river. Lush greenery lines the opposite bank, and a clear blue sky with scattered clouds adds to the serene environment. A table and chairs are visible on the deck, inviting relaxation by the water.
Cabin in Waddington
4.92 out of 5 average rating, 109 reviews

Waddingtons Getaway!

This rustic Cabin is located on Big Suckerbrook in the Village of Waddington, just a few miles from where the Bassmasters is hosted! There is dock access, kayaks and canoe for use and swimming! This is the perfect fishermen, family or friend get away! With the cabin sitting a mile off the highway it makes for a very peaceful stay.

Popular amenities for Winchester Springs holiday rentals