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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!

Guest favourite
A spacious king size bed with soft bedding is positioned against a wall with three large windows above. Two lamps on either side of the bed provide gentle lighting, complemented by a ceiling fan and a serene view of the surrounding outdoors.
Bungalow in Kemptville
4.92 out of 5 average rating, 107 reviews

South Suite - at Abbott Road Suites

Beautiful 600 square foot suite, in an executive bungalow, totally private without any shared areas. King size bed, walk in slate shower, private entrance. Tastefully furnished with Egyptian cotton bedding, a couch, reclining chair, plus dining table and chairs. Fridge, freezer, microwave, cooktop, convection oven, coffee maker, kettle, with all dishes,cutlery and cookware provided. A beautiful view of the quiet, rural property. 5 minutes to downtown Kemptville. Access to a washer/dryer too!

Guest favourite
A grassy area is highlighted by a large tree featuring a playset with a slide. In the background, tranquil water reflects the sky, while a shed stands nearby. The scene is framed by scattered clouds and greenery.
Apartment in Edwardsburgh/Cardinal
4.88 out of 5 average rating, 163 reviews

1000 Islands waterfront accommodation

Amazing hot tub & patio both with awesome river view!-DSL hi-speed wifi-17 min Brockville-Gorgeous 1000 sq ft walk-out St. Lawrence River secluded waterfront accommodation! Ambient in-floor heating to compliment beautiful gas fireplace! Grand rm features custom kitchen with hand-crafted pine cabinetry & a wall of 4 very tall south-facing windows/patio doors-Hi-end 4-piece bath-Mstr quarters offer king-sized bed/his & hers closet space-2nd bdrm has queen murphy bed-Enjoy kayaks/fish from dock!

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.

Top Guest favourite
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, 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
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, 256 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.
Apartment 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 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
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, 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
A fire pit surrounded by large, smooth stones is seen at dusk, with flames dancing warmly against a backdrop of the Ottawa River. The calm water reflects the soft evening light, and distant hills outline the horizon.
Guest suite in Dunrobin
4.99 out of 5 average rating, 262 reviews

Tranquil Getaway on the Ottawa River

Welcome to River Edge. Our studio suite is sparkling clean, elegant and ready for you. Enjoy up close, the peaceful view of the Ottawa river and the Gatineau hills. Just 40 minutes from downtown Ottawa, our neighbourhood is one of the best kept country-living secrets of the NCR. River Edge is best suited to guests who prefer tranquility, peace and restful quiet.

Popular amenities for Winchester holiday rentals