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Holiday houses in Winchester

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Top-rated holiday rentals in Winchester

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Guest favourite
The exterior of a charming two-story building is illuminated by a warm glow from the interior. A fire pit with a crackling fire is positioned in front, surrounded by wooden Adirondack chairs. Tall trees frame the scene under a twilight sky.
Cabin in Ingleside
4.89 out of 5 average rating, 150 reviews

Lost Village Guest House 1860s Renovated Barn

Original 1860 Building Moved From The Lost Villages During The St Lawrence Seaway Project. Lots of Character & Charm❤💕 Whether You’re Looking To Soak Up The Sun At The Beaches, Have Fun On The Water, Bike Around The Parkway, or Enjoy The Sledding Trails and Ice Fishing In The Winter Months. Enjoy The Natural Light Offered In Every Area of The Home. This Home is Dedicated Exclusively To Airbnb Guests And Sleeps Upto (2) Adults Comfortably Ideal For Any Vacation, Renovation or Work Stay!

Top Guest favourite
A secluded guesthouse is shown, featuring a rustic exterior with grey wood siding and a vibrant red door. A path leads to the entrance, complemented by a welcome mat and a recycling bin. Flowering plants add a touch of color to the outdoor space.
Guesthouse in Newington
4.92 out of 5 average rating, 525 reviews

Trees, open spaces, and the milky way at night

8 min. from 401 & St Lawrence River, at Ingleside, pet friendly, secluded studio guesthouse, tranquil, safe location for those seeking a road break or destination traveler's seeking the St Lawrence and its environs. Sit by a fire, listen to wind and birds or watch the sky. $50 cleaning fee per pet through extra fee request if necessary before arrival. There is no reliable internet but good cell coverage available; the smart tv can tether to your own device and streaming service provider.

Guest favourite
A cozy loft space features a spacious bed with neutral bedding against a vibrant teal wall. A small dining area with a table and chairs sits to the left. Soft lighting highlights the contemporary design, while a wardrobe and bookshelves add functional accents to the space.
Loft in Cantley
4.84 out of 5 average rating, 300 reviews

Breakfast box included-Spa/sauna dispo with extra$

Private Studio, with no direct interaction with the hosts. About 15 minutes from Gatineau and 20 minutes from Ottawa by car. For an additional fee (and subject to availability), you can access the spa, sauna, and cold plunge pool. A lunchbox breakfast is included. Perfect for workers or tourists. We have 2 dogs and a cat (they do not have access to the studio). The studio is independent, yet attached to the house, and we ask visitors to maintain an appropriate noise level during their stay.

Top Guest favourite
Townhouse in Gatineau
4.98 out of 5 average rating, 297 reviews

Trendy basement- 10 mins to downtown Ottawa

CITQ 302220 - Come and enjoy our bungalow with free parking and everything you may need for confort. We are less than 2 kilometer away from either the « Centre sportif de Gatineau », « Maison de la culture», and the « Centre Slush Puppy » . We are but a few kilometers away from the downtown Ottawa core, Gatineau Park, several museums, Nordik Spa, Casino du lac Lemay, Byward Market, Rideau Canal, various restaurants and night life. Ideal for couples, small families and business travelers .

Top Guest favourite
A bright living room is shown, featuring a leather couch and a cozy red armchair. A wooden coffee table rests on a light-colored rug, while a decorative piece hangs on the wall. Large windows allow natural light to fill the space, offering views of the outside.
Guest suite in Nepean
4.89 out of 5 average rating, 158 reviews

Forest Suite in the City: 1bd/1bth + parking

Take it easy at this unique and tranquil getaway. Located 12 mins from the airport and 18 mins from downtown, this private guest suite is attached to our family home nestled in Pinhey Forest, with access to over 5km of year-round trails. You will have the use of your own private entrance leading to a full suite, including a fully-stocked, eat-in kitchen; 4-piece bath, queen bedroom with closet space, and a bright and cozy living room with smart TV. On-site parking is included.

Top 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, 257 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
The cabin is set amidst tall trees, illuminated by warm interior lighting that highlights its log construction. The night sky sparkles with stars above, while the surrounding foliage creates a natural, secluded ambiance.
Cabin in Plantagenet
4.92 out of 5 average rating, 425 reviews

PERCHED CABIN at Mariposa Farm

The Perched cabin is one of our three cabins. We also have the Apple Tree and the Poplar cabin. This is glamping at its best. Window walls letting light into every side. A sleeping loft. Built with logs. Well equipped for cooking. Heated with woodstove - firewood included. In the middle of the forest. A lot of trails to enjoy. No neighbours. The perfect spot to unwind. We are farmers, a precise time of arrival is important. You are welcome to visit the farm.

Top Guest favourite
A wooden dock extends into the water, featuring two Adirondack chairs facing the river. Behind, a modern home with a large window displays a Canadian flag and a unique barrel sauna. Lush greenery surrounds the setting, providing a peaceful atmosphere.
Cottage in Kemptville
4.83 out of 5 average rating, 100 reviews

Rideau River Retreat - Waterfront Home

Relax with the whole family at this peaceful all-season home on the Rideau River, only 30 minutes from the heart of Ottawa and 5 mins to Kemptville. Take in the river view while relaxing inside our Cedar Barrel Sauna or sipping morning coffee on the dock. Easily explore the neighbouring towns of Manotick and Merrickville or boat, fish, kayak, or canoe in the middle of the largest stretch of the Rideau River (46km of open water from Manotick to Burritts Rapids).

Top Guest favourite
The A-frame chalet is set against a backdrop of vibrant autumn foliage. Its striking black exterior contrasts with warm wooden accents. A large glass front showcases an inviting interior, while a stone terrace framed by fallen leaves adds to the natural ambiance.
Chalet in Val-des-Monts
4.97 out of 5 average rating, 143 reviews

Les Refuges des Collines – Gatineau Park

On the shores of a lake, Parc de la Gatineau is a superb A-frame chalet perfect for disconnecting from the city while being ideally located to allow you to enjoy all that the Gatineau/Ottawa tourist region has to offer. Our mini-chalets are equipped to allow you to relax with their hot tub or to telecommute in their office equipped for this purpose. Our chalets will be a place you'll be eager to return to, as you'll feel at home here.

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, 189 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
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, 108 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
A modern living area showcases a light-colored sofa positioned near a cozy bean bag. Natural wood accents are visible in the dining area, featuring a round table surrounded by dark chairs. Soft lighting highlights the open space, contributing to a bright and airy feel.
Apartment in Ottawa
4.98 out of 5 average rating, 132 reviews

Whispering Timber Suite

Enjoy the peaceful calm of being surrounded by nature in Whispering Timber suite. You'll have exclusive access to the in-law suite of our home, complete with a bedroom (queen size bed), a sofa bed, a full bathroom and a small kitchen. The suite is located at the back of the home with it's own exterior entrance. Extra towels, sheets and comforters are provided, along with dishes and cookware in case you want to make a meal.

Popular amenities for Winchester holiday rentals