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Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

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

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Top guest favourite
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 favourite
A welcoming entrance to the studio guesthouse is framed by vibrant yellow chrysanthemums in a large terracotta pot, alongside decorative pumpkins, one orange and one white. A small blue birdhouse adds a charming touch near the steps leading to the door.
Guest house 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 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, 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 favourite
Guest house in St-Albert
4.97 out of 5 average rating, 33 reviews

1 Bedroom Furnished Guest House

Discover the perfect blend of comfort and convenience in our smoke-free guest house attached to our home. This furnished space features: - Free Parking - Internet Access - Cable TV: For your entertainment. - Washer/Dryer: In-unit laundry. - Complete Kitchen: fridge, stove, and microwave - Queen Size Bed - Private Entrance - Patio: Extend your living space outdoors with access from both the bedroom and living room. - Generac Generator: Peace of mind with a reliable backup power source

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
4.9 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.

Top guest favourite
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 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).

Guest favourite
A well-maintained garden path is surrounded by lush greenery and flowering plants. A gazebo with seating is visible in the background, providing a shaded area for relaxation. A trellis adorned with climbing vines leads towards the gazebo, enhancing the peaceful outdoor setting.
Flat in Williamsburg
4.72 out of 5 average rating, 122 reviews

Kim's Country Retreat

Come and stay in this cozy cottage-like century home/apartment complete with pine wood flooring accented with country antique decor. Clean, bright and quiet. Perfect for travelers, long and short term temporary workers or students. 10 minutes south to Morrisburg amenities, and Hwy 401. 10 minutes north to Winchester amenities, and Hwy 43. Kemptville and 416 is only another 20 minutes. Easy commute to Ottawa, Brockville or Cornwall.

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, 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 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.
Flat in Ottawa
4.98 out of 5 average rating, 131 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 favourite
Holiday home in Kemptville
4.9 out of 5 average rating, 123 reviews

Boathouse Café Airbnb

Getaway at our stylish and open concept airbnb just steps from the Rideau River. Our Airbnb boasts views of the Rideau locks from the front, and of our 6 acre property from the back. Take our canoe or paddle boards out on the river, enjoy a campfire under the stars, hike the nearby trails, or go exploring in the nearby town of Merrickville. Enjoy your own private courtyard with dining table, BBQ, and lots of privacy.

Popular amenities for Winchester holiday rentals