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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!

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.
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
Cottage in Kemptville
4.98 out of 5 average rating, 43 reviews

Rideau River Getaway Waterfront 30min to Ottawa

Welcome to the Rideau River Getaway! A serene 4-season retreat just 30 minutes from Ottawa. With breathtaking sunset views, a 70-foot dock, outdoor kitchen, and Starlink WiFi, it’s the perfect escape for families, couples, and friends. Enjoy kayaking, paddleboarding, fires by the water, and hikes right across the river. Inside, relax in a newly renovated home with luxurious touches, top-tier appliances, and space for up to 8 guests. Peaceful, private, and packed with charm.

Top Guest favourite
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
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.

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