Holiday rentals 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, 141 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 cozy bedroom is highlighted by a plush queen-sized bed, adorned with soft linens and a decorative throw pillow. Two bedside lamps provide warm light, while floral artwork hangs above the headboard, enhancing the serene feel of the space.
Flat in Kemptville
4.97 out of 5 average rating, 31 reviews

Road trip Luxury Private Guest Suite off 416

Our super clean cozy private entrance guest suite just off the 416 in the quaint small town of Kemptville (20 min from Ottawa) can often host last minute bookings. The suite is separated from the rest of the house by a locked door and there are no shared spaces. The self contained suite has a queen-sized bed, 2 TVs, couch, chair, desk, mini-fridge, microwave, coffee-maker. On the main level of a bungalow. Not in a basement! 10 foot ceilings, tons of light! Must have car, no uber, no transit.

Superhost
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
4.91 out of 5 average rating, 104 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 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.
Guest house in Newington
4.92 out of 5 average rating, 507 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 well-lit entrance features a decorative front door with a glass pattern, complemented by a small bench and shoe rack. The tile floor extends throughout, while beige walls provide a neutral backdrop. Natural light filters in, enhancing the welcoming atmosphere of the entryway.
Guest house in St-Albert
4.96 out of 5 average rating, 28 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 vibrant sunset illuminates the sky with shades of orange and pink, reflecting on the calm water. A boat is docked at the edge of the water, with the serene landscape framed by trees in the background.
Cottage in Kemptville
5 out of 5 average rating, 37 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
A welcoming living area is observed with a sectional gray sofa and an accent chair in turquoise. A small coffee table is situated in front of the sofa, and a decorative area rug adds warmth to the space. Natural light is provided by large windows.
Home in Winchester
4.96 out of 5 average rating, 179 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. Check us out at theloftynest dot ca.

Top guest favourite
An open-concept living area is illuminated by recessed lighting, featuring a dining table with four cushioned chairs. A spacious seating arrangement is visible in the background, alongside a fireplace, framed by neutral-colored walls and natural wooden accents. Greenery adds a touch of vibrancy to the space.
Home in Manotick
4.94 out of 5 average rating, 217 reviews

Spacious Walk-Out Basement with Scenic Views

Spacious, private walk-out basement with a separate private entrance. The basement includes a large living room, dining area, kitchenette, bedroom + ensuite bathroom (includes standing shower and bathtub), walk-in closet, and patio area. Access to WiFi, TV (shows+movies), mini fridge, microwave, hot water kettle, air fryer, coffee maker, countertop flat burner, & toaster. Located close to highway 416, Manotick Downtown, and Barrhaven Marketplace.

Superhost
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
4.71 out of 5 average rating, 116 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
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, 108 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.

Guest favourite
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.
Flat in Prescott
4.98 out of 5 average rating, 117 reviews

Ships and Stacks. Ship/River themed 1 Bed Suite

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 favourite
The modern home features an inviting wooden deck leading to an entryway with large windows. A red metal roof complements the dark exterior. Surrounding the house, tall trees add to the serene setting, while a well-maintained lawn extends before the structure.
Cottage in Ottawa
4.9 out of 5 average rating, 183 reviews

Beautiful Waterfront Home | 30 Minutes from Ottawa

Escape to a serene 3-acre waterfront retreat on the beautiful Rideau River, just 30 minutes from Ottawa. Modern home with 400 feet of shoreline, situated next to Baxter Beach and the scenic trails of the Rideau Valley Conservation Area, it’s the perfect spot for outdoor enthusiasts. Riverside patio, complete with a fire pit and BBQ, as you take in stunning sunsets and the peaceful surroundings. A heavenly getaway!

Popular amenities for Winchester holiday rentals