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Vacation rentals in Winchester

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Top-rated vacation rentals in Winchester

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

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Top guest favorite
The living room features a spacious gray sectional sofa, accented by orange throw pillows. A round coffee table is positioned on a decorative rug, with a television mounted on the wall above a gas fireplace. Natural light fills the space through large windows adorned with sheer curtains.
Townhouse in Ottawa
4.99 out of 5 average rating, 422 reviews

Large family home: Downtown. Airport. Shops. River

WELCOME To this stylish large new house in the upscale safe neighborhood of Riverside South, Ottawa. Perfect for families, co-workers & friends GREAT LOCATION 2 min to shopping, Park & Ride, Rideau River, parks & trails. 10 min to Barrhaven Town Center with all major stores & restaurants. 11 Min to Via Rail – Fallowfield Station. 14 min to airport, E&Y Centre Amazon, 416, and 417 hwy 21 min to TD Place stadium 24 min to downtown. 26 min to Canadian Tire Center. We can't wait to host you!

Top guest favorite
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.

Top guest favorite
The exterior of a two-story brick home is visible from the water, surrounded by lush greenery. A staircase leads from the riverside to the upper level. A patio is seen above, along with a small dock featuring seating by the water's edge.
Guest suite in Ottawa
4.99 out of 5 average rating, 121 reviews

RiverBend Landing near Mooney’s Bay

Cottage life in the city! You will be close to everything in the Nation’s Capital when you stay at this prime location on the banks of the Rideau River. Just a 15 minute drive to the Ottawa airport, 8 minutes to Mooney’s Bay Park & Beach and easy access to Colonel By Drive for a scenic 20 minute trip to the popular Byward Market. You are welcome to sit by the water, or enjoy the patio with a view and a beverage! In the winter months, access to the Rideau Canal Skateway is 5 minutes away!

Top guest favorite
A charming bungalow is surrounded by a well-maintained yard with a large tree displaying vibrant autumn foliage. The front of the house features multiple windows adorned with flower boxes. A paved driveway leads to a carport on the side.
Townhouse in Gatineau
4.98 out of 5 average rating, 295 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 favorite
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
4.9 out of 5 average rating, 157 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.

Guest favorite
The image features a well-lit entryway leading into the living space, showcasing a modern green armchair beside a large potted plant. A glimpse of the bedroom is visible through an open door, with light-colored bedding and a small shelf in the background.
Guest suite in Sandy Hill
4.9 out of 5 average rating, 250 reviews

Cute 1-bedroom suite steps from downtown

Take in the best of Ottawa while relaxing in a newly-renovated suite in the heart of the city. Clean, modern and stylish with a comfy bed, private bathroom and living room with TV, microwave and mini-fridge. You'll be steps from the University of Ottawa, the Rideau Canal, and historic Strathcona Park. Just a five minute walk to the O-Train, giving you easy access to everything the nation's capital has to offer. Downtown and the Byward Market are within walking distance.

Top guest favorite
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, 254 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!

Top guest favorite
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 favorite
A large mural featuring a vintage ship against a textured brick wall adds character to the space. The artwork includes the text 'Ships and Stacks' and 'The Future of the St. Lawrence Seaway,' reflecting the local maritime heritage.
Apartment in Prescott
4.98 out of 5 average rating, 117 reviews

Mid-term Stays - Nov to June - 1 Bed Suite

Mid-term stays Nov-June. Nautical-themed, luxurious and romantic 1 bedroom suite. Enjoy your own 1100 sq/ft space in downtown Prescott (1 block from the River). With an industrial, modern design, this space showcases unique and custom art, literature and partial river views. NOTE: Unit access is from the exterior stairs only. This unit is on the 3rd level and is not recommended for individuals that may struggle with stairs or heights.

Top guest favorite
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, 188 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 favorite
Apartment in Ottawa
4.98 out of 5 average rating, 130 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.

Top guest favorite
A modern A-frame chalet is nestled among tall trees, featuring a unique sloped roof and large windows that allow natural light to filter in. Soft illumination from inside enhances the cozy atmosphere, while the natural surroundings create a sense of tranquility.
Chalet in Val-des-Monts
4.97 out of 5 average rating, 119 reviews

Haven at the Hills - Lac McGregor

Near a lake, the McGregor is a superb A frame cottage, perfect for disconnecting from the city while being ideally located to allow you to fully enjoy everything the Gatineau/Ottawa tourist region has to offer. Our mini-chalets are equipped to allow you to relax with our spa or to work remotely in our office, according to your needs. They will be a place you'll be eager to return to since you'll feel right at home there.

Popular amenities for Winchester vacation rentals